Yes. The horrible metal poles and covered sidewalks that protrude from the most stunning hundred-year-old New York buildings. The structures that make you duck your head, reroute your path, question whether the building is crumbling behind the tarp.

But sometimes they block the rain. Sometimes they stop the sun.

That’s me right now. Not the finished façade. The reinforcement New Yorkers roll their eyes at and pray will be gone by spring.

A couple weeks ago, on the eve of the Chinese New Year, which I suddenly knew a lot about because the algorithm decided I should, I was sitting on my couch unbathed, eating chicken satay out of a cardboard container when I learned that showering before midnight could rinse away your abundance.

A woman on my feed explained, very calmly, that if you washed your hair you could literally cleanse your incoming wealth down the pipes.

I looked at my bathtub.
I looked at my skin.
I considered the stakes.

Maybe soaking is different. Maybe soaking allows abundance to marinate.

So I just didn’t wash my hair.

This is what my brain does when left alone with a future. Everything becomes a lever.

Cynthia told me this week that I’ve been forcing things my entire life. Forcing relationships. Forcing timelines. Forcing versions of myself to emerge before they were ready.

“That’s not how things work,” she said, like someone explaining gravity.

The forcing always felt productive. Heroic, even. If I just push hard enough, this will work. If I optimize the timing, I’ll arrive faster.

Now she wants me to move differently.

Not: How do I secure this?
Not: How do I make him choose me?
Not: How do I get to the end?

Lay the foundation. Then stop interfering.

Which, for me, looks like not sending the second text. Not following up on a job five times in one afternoon. Not refreshing the thread. Not assuming silence means everyone secretly hates me.

I don’t know how to stop interfering with life. Waiting feels like decay.

So on Friday, I tried an experiment.

I went to San Vicente Bungalows — the place that makes you put a sticker over your phone camera so you physically cannot document your own existence — wore something slutty but appropriately stylish, ordered a martini, and decided I would not manage the night.

I stayed with my friends. I ate zucchini chips. I let my shoulders drop.

Someone who has hovered in my orbit came over. We talked. He went back to his friends.

There was a version of me who would have drifted over, inserted herself into the group, engineered another ten minutes, an hour etc.

I stayed seated.

It was barely visible.

But for me, it was seismic.

Cynthia also said something that lodged itself under my rib cage:

“Your subconscious is using your free will to say no to what your conscious mind wants.”

I can consciously want peace while subconsciously remaining loyal to chaos because chaos feels like home. I can consciously want someone steady while still being magnetized by the one who withholds.

Starting something new again has always felt humiliating to me. Like admitting I miscalculated.

But scaffolding isn’t demolition. It’s reinforcement.

You can’t tell it’s protecting something beautiful. It just looks like an inconvenience. A why are you here?

Last week in the middle of the night, I hallucinated a spider the size of a cereal bowl in my bedroom. I stared at it for ten seconds. It didn’t move.

Instead of nudging someone beside me, there was no one to nudge, I opened my laptop.

“There is a life-sized daddy longlegs crawling on my window?” I typed.

My resident AI exterminator responded: “A cereal bowl–sized daddy longlegs in a New York apartment is unheard of.”

The last time this happened in my old apartment, I made a guy come over and throw a shoe at it. It was a mark on the wall.

The reflex I dislike most in myself is the one that whispers: You need someone to save you.

Which is absurd. I have survived every single thing that has happened to me. Objectively, I am competent.

And yet there is still that murmur.

The scaffolding, I think, is the space between those two voices. The part of me that reaches for rescue and the part that knows I can stand still on my own.

Because this is the real pattern:

I step forward and then I pull back.

I host one How to Function event and disappear.
I post four things on Instagram and decide I’m awful.
I get close to someone and then mentally step outside the moment.
I move toward visibility and retreat before anyone can fully see me.

It’s subtle. No one calls you out for it. But I notice.

So here’s the experiment:

What happens if I don’t pull back?

If I post for eight weeks straight as myself and see what happens.
If I don’t delete it.
If I don’t vanish after.
If I let the tarp flap in the wind and don’t apologize for it not being cute yet.

No dramatic relaunch. No “new era.” No savior arriving to steady the beams.

Just repetition.
Just staying.

I’m in the construction zone. I might be here for a minute. And like most construction in New York, it will probably take longer than the original estimate.

Somehow, functioning,
Jilly

Not in a sexy way — though I guess that depends who you ask. The kind of move you make when you’re trying to manufacture confidence with whatever is available in your apartment.

I stood in front of the mirror thinking: if my life is going to feel uncertain, at least my boobs can feel supported.

I’m exposed on every front at once.

Romantically: I reached.
Professionally: the story isn’t shiny.
Socially: I can’t control the narrative.

For most of my adult life, I survived by being able to say one simple thing: There is a plan for my life.

I’ll make content. Start businesses. Make money. Fall in love at the correct time. Get married in a devastating beautiful Mugler piece. Have children in Tribeca as a career woman with a double stroller. Even when things were chaotic, there was always a storyline. A forward-facing explanation. Something I could point to and say, relax, it’s building.

Right now, I can confidently tell you I have no idea what my life is going to look like.

Not because nothing is happening, but because whatever is happening doesn’t come with a headline. There’s no carousel post with “big changes 🕊️” and a comment section full of congratulations.

Of course I want things. In fact, my desire feels almost offensively alive right now. I want love. I want sex. I want a book deal (and yes, I will tell you that every week). But for the first time, I don’t feel like I need to know the direction of my life. TikTok astrologer Tali is losing his grip on me. Don’t worry, Cynthia will stay forever, but for once, I’m not asking her to fix me.

Will I fall in love? Will I have a child on my own? Will my writing turn into something bigger than a Substack and a dinner reservation?

I’m deeply uncomfortable with uncertainty. And the universe is forcing me to surrender.

So I’m just… here. Unwrapped.

Which is probably why I double texted that man. “Would love to see you again.” I spiraled for twenty-four hours and then realized: this is living.

I don’t think I’ve double texted since I was drunk at Boston University after Marathon Monday, emotionally unstable, wearing a romper that should have been illegal. I don’t put my cards on the table. They’re usually stacked neatly in the box, all accounted for. The queen of hearts never missing.

But this time, I let a man see me wanting. No irony. No strategic delay. No “haha just kidding.”

I reached.

And when he didn’t respond, my nervous system didn’t just register romantic rejection, it registered exposure. Of course he ignored you, my brain said. Look at you. No shine. No buffer. No storyline. No proof of arrival.

But then… it didn’t land like you suck. It landed like: oh. This is the cover charge.

Then I went to a birthday party where I knew I would see everyone I’ve ever crossed paths with in New York. Work people, Hamptons people, a weird late night from Paul’s Baby Grand. The kind of faces that make you realize New York is both massive and claustrophobic at the same time.

My social anxiety was off the charts. I almost didn’t go. But I put on the strapless dress. I committed to the socks.

My nervous system treated the possibility of being judged like it was the final boss of my entire self-worth. I acted like I was preparing for war, when really I was preparing to stand near a DJ booth and scream into someone’s ear, “I LOVE THIS SONG!”

When a friend from ten years ago asked for an update, I didn’t package anything in a bow. I just said: I don’t really know what’s going on with my life. And instead of feeling embarrassed, I felt strangely… fine. The a Polaroid artist asked to take my photo and then tried to slow dance with me. I said, gotta run.

It feels weird to move through life with no storyline. Everyone you meet has an identity based on their job, their love life, their neighborhood, their clothes. We all want to be defined. Placed in a category we want to be perceived by. Something we can tie up in an Instagram bio bow.

Founder.
Mother.
Wife.
Brat.
Skincare minimalist with a French bob.
Corporate baddie with a matcha addiction.

It almost makes other people more comfortable when they know where you fit. But what happens when you have none of that?

Who are you in 2026 without a headline?

I saw the news about James Van Der Beek this week. It hit me hard. He’s 48. My aunt died of lung cancer at 42. I think about her every day.

And I found myself wondering: what am I doing being so afraid of being seen? Of being wanted? Of being rejected? Of being unfinished?

If the whole point is that we get one life, why am I spending mine trying to be impressive enough to deserve it?

The very thing I’ve been fighting my whole life is the idea that I could be lovable just as me. Not as potential. Not as momentum. Not as future wife, future founder, future something.

Just me.

And weirdly, this is also the moment I’ve been asking for.

I said I wanted to live.
I said I wanted to feel desire.
I said I wanted to be present instead of managing the narrative.

Well — this is what that costs.

You don’t get to control how you’re perceived.
You don’t get to edit the scene after it happens.
You don’t get to be both untouchable and alive.

So no, this isn’t a tragedy. And it’s not a comeback story either.

It’s an adjustment.

Which might be the most honest chapter yet.

Somehow, functioning,
Jilly

My friend Nicole brought a case of beer for the chefs, which is sort of an opening-night ritual in restaurants. I’m stealing that move next time.

I ate, I sat at a table, I remembered what it feels like to be a person with a life. The kind of night where you’re surrounded by people talking too loudly about things that don’t matter, and it almost makes you believe nothing matters. In a comforting way.

Then I went home and returned to my regularly scheduled programming.

I don’t know if it’s trauma that hardened into my nervous system or just the background noise of being alive right now. On paper, I’m doing well. I get out of the house. I work a lot. I work out. I eat relatively healthy. I take care of myself. I do all the things you’re supposed to do when you want your life to look like it’s functioning.

But mentally, I keep circling the same question:

How is anything in my life going to work out?

I did the unthinkable and kissed the guy from last week’s column. Turns out I did not forget how to kiss. We’ll leave it at that.

I don’t think it can go anywhere, which is… familiar. The pattern where something exciting happens, my nervous system briefly wakes up, and then reality taps me on the shoulder like, let’s not get ahead of ourselves.

Still, there was an energy between us I don’t feel often. Not enough evidence to call it anything, but enough to remember what it feels like when something might.

It felt light. Not heavy. Not complicated. Not like I needed to decode him like the CIA, or worse, like a man on Raya. It felt like being with someone in the moment. Which is a sensation I forgot existed.

And the truth is, what made it special wasn’t him. It was me. I wanted to be seen. I wanted to be there and think, this is me. No performance. No armor. Just me, in all my flaws. My imperfect stomach. Whatever sadness lives behind my eyes. The TikTok posture.

Normally, I just want to hide. But for a few hours, I didn’t.

Of course, sometimes I think human touch is a scam. Because the second you get it, you remember what it feels like to be a human being. And then when it’s inconsistent, you start wondering if it would be better to never have it at all. Like abstinence isn’t about purity. Maybe it’s about avoiding the emotional whiplash of remembering you’re alive.

But then I end up in the same place. Not putting myself out there. Not living my life. Calling it self-protection. Branding my avoidance as awkwardness, as if avoidance is just a quirky personality trait.

I also went out dancing. I sang karaoke. I did things I would normally punish myself for, like staying out, being loud, taking up space. For a few hours, I felt free.

Then I spent the rest of the weekend punishing myself for it.

I went to an event for my friend Lauren and met Ali Kriegsman. She was impressive in the way that actually impresses you. Grounded. Clear. Fully herself. I’ve been reading her Substack, New Motives, for a while, and it’s strangely comforting to meet someone whose work you already let into your brain every week.

I saw a video this week that said to draw a line down a piece of paper. On the right side, write your name. On the left side, write “The Universe.” Then list everything you’re responsible for on your side, and everything you’re going to let the universe handle on its side.

My side was mostly logistical. Write the weekly Substack. Take care of my body. Pay bills. Don’t spiral.

The universe’s side was more ambitious. Bring me a book deal. Bring me the right man. Make the money part make sense. Please handle whatever is happening to my nervous system.

I’m not asking for much. Just a stable brain, some literary luck, and maybe a husband.

There’s constant information. Instability. Violence. Economic pressure. Climate anxiety. None of it is abstract anymore. It lives in our bodies. Even the most emotionally avoidant person you know is starting to develop opinions and feelings, which is honestly how you know it’s bad.

We lost believable futures. A lot of the timelines we were promised quietly disappeared, and now we’re improvising without a script. Everyone is pretending they’re fine, because that’s what adulthood is now. Functional denial with a skincare routine. Perfect skin, dead eyes.

We optimized away meaning. We got very good at productivity and very bad at metabolizing feeling. We turned our inner lives into something we manage like a business.

So my fear doesn’t always look like sadness. Sometimes it looks like confusion. Irritability. Fear without an object. Fatigue that rest doesn’t fix. Asking what’s the point while still going to Pilates. Functioning without feeling alive.

I’m incredibly hard on myself in ways I don’t fully understand yet, and some days I don’t see the point.

Cynthia told me that when your purpose becomes bigger than yourself, you stop worrying so much about what people think because you’re focused on helping. I’m starting to understand what she means. Not fully. But enough to feel it flicker on.

I am really struggling with my mental health right now. And that’s okay. For a long time, I was trying to fight it, as if I could outwork my own nervous system. Accepting it doesn’t mean I can’t be successful or have the life I want. It just means this will always be part of the picture. It has been here. It will probably stay. Letting that be true sometimes makes it feel lighter.

I know I’m not alone. A lot of people are depressed. Or something adjacent to it. Or living in a prolonged stress response and calling it a personality.

So this week I’m just sitting with it and asking the universe to be extra kind.

Somehow, functioning.
Jilly

PS. Would love for you to follow the How To Function Instagram <3
Thank you for being here.

This transformation has included approximately twenty-five panic attacks. The kind where it feels like an exorcism moves through your body and leaves behind someone marginally calmer. Is this quantum leaping? Probably not.

I told my gynecologist this yesterday, as if she were Cynthia. When she asked the standard intake questions, how often do you drink, do you do drugs, I said, “I’ve been calming myself with weed gummies more than I’d like to admit this month.” She smiled, nodded, and told me I should really freeze my eggs if I want to have children. A conversation you and I will be getting into next week.

My January days broke into strange shifts: four hours where I’m fine, four hours where I spiral, four hours where I feel almost happy. I don’t know who scheduled it like that, but it’s been consistent, so I’ll give my brain that.

In exciting news, I finally went on a date.

As I publicly stated on Instagram, this was the first date I’ve been on in a year. I didn’t post that part because I think I’m embarrassed. Dating and relationships still feel like a rite of passage I somehow missed. At this point, I genuinely couldn’t tell you if someone even locked eyes with me last year.

This week, I think I finally came out of the tunnel of darkness, or at least into a dimly lit hallway that looks promising. Like the rest of the world, I’m very much preparing to shed the snake and become a horse on February 17th. I’m so excited about it I’ve considered throwing a party.

On Friday at Casa Cipriani, a man I was flirting with, with the utmost confidence, said, “I want to make out with you in the bathroom.”

Somehow it worked.

I replied, “Do you want to have children?”

A fair question, considering he’s a divorcé with kids (something OG readers may remember my astrologer once predicted I would marry).

Very calmly, he asked, “Do you need to know that before you make out with someone?”

He had a point.

The last time energy like that stopped me in my tracks was mid-conversation with Michael B. Jordan. This man was no Michael B., though I did just watch Sinners, which, alongside The Academy, I would personally give sixteen nominations to.

Naturally, I left Casa Cipriani without the make-out. That night, I replayed the moment the way I replay most things: from every angle, with revised dialogue, as if one version might unlock a better ending. None of them did.

When I say I want to be having more experiences, what I mean is that I keep stopping myself right before they happen. I want to be vulnerable, but my subconscious intercepts it, like it’s doing its job, like it’s saying: this is how you get hurt. I don’t fully want vulnerability. If I did, I’d already have it. But I want to want it, which feels like its own kind of work.

Last week, I caught myself almost arguing with an ex-lover, if you can even call him that, over text. I stared at my phone and thought: would the person who has everything I want behave like this? Would she go back and forth like this over text? Would she refresh the thread like it was a stock ticker?

I hate to admit that a man brought this revelation about. But that’s when it clicked.

I need to become the person who can hold the person I want to be.
That’s the work.

So that’s the goal right now: becoming someone who can hold real love, business success, money, and difficult conversations.

I’ve made enough wrong decisions that my confidence isn’t built on intuition. It’s built on survival. I always land somewhere eventually. But that’s not the same as landing where I meant to go. And I want to be where I’m meant to go, even if it means being seen in a way my body is terrified of. I don’t want a life that’s technically fine but secretly full of abandoned versions of myself.

That shift really started with hosting the first How To Function event. Desiree Pais from Benshen.Co hosted at 113 Spring (thank you to In Search Of). We started with a prompt, what are the holding patterns of my life, and dissected where we get stuck and why. Watching people get something real out of the exercise felt genuinely profound, maybe the best I’ve felt in a long time.

It’s the direction I want to go in, and I’m grateful to you for reading this column, because it’s what got me here. I’ll be hosting another event in February and would love to invite you.

Most of the time, I don’t even know what I’m afraid of. Maybe that living will hurt too much. My mind tries to protect me and, in doing so, quietly shrinks my life. I feel things deeply, and I’ve spent a long time treating that like a flaw instead of embodying it.

I am, at my core, just a girl who loves to talk, write, discuss, and make things all about feelings. So I guess that’s where I should lean the fuck in.

Joan Didion said confidence is having the courage of your own mistakes. I don’t think I have confidence. And I’m not sure I ever will. But this is a start.

Somehow, Functioning,

Jilly

I have one governing rule for my wardrobe: if I’m not obsessed with it, it leaves. I’ve learned that a closet is a living thing — it only works when every piece earns its place. I’d rather own fewer items I reach for instinctively than a crowded archive of “maybes.” Even a simple Wolford top has to hold its weight. Clothes, makeup, skincare, the rule applies across the board. I buy what I use. I wear it until it becomes part of my personal mythology. Then I replace it or send it back into the world via resale sites.

Most of what’s in this guide comes straight from my life. A few pieces are vintage. Almost all of them can be found on resale platforms, which is usually where I begin. So don’t feel tethered to these exact links — half the pleasure is spotting the thing in the wild, or finding it on Vestiaire at 40 percent off in suspiciously immaculate condition.

This isn’t a shopping list. It’s a snapshot of the objects that have survived the edit. The inner architecture of my closet-brain. Maybe it will remind you of something you already own, or inspire you to find the version that feels like you.

getting ready for the function,

xx
Jilly

JIMMY CHOO Boots, Maison d’etto Perfume, Kallmeyer Jacket, Kallmeyer Dress, Vintage Fendi Baguette, Martini Glasses

Manolo Pumps, Rotate Midi Skirt, Vintage Fendi Baguette, Manolo Slides, Vintage MiuMiu Midi Skirt, Wolford Strapless Top, BODY Vodka, It Girl, J’Adore Vintage T

Matte Bra, Matte Leggings, Facile Gloss, Loewe Bracelet Bag, Eterne Tank, Kallmeyer Pants, Seven Spiritual Laws of Success, YSL Boots, MPH Lip Ciggy

Sézane Boots, Kerrie Jeans, Rafs Hat, BonBon Candy, Sézane Makeup Bag, Flamingo Estate Candle, Summer Fridays Gloss, Nour Hammer Coat, Jurlique Oil

Cissa Halter, Caro Jeans, Experiment Lip Treatment, Magic Molecule, Mirror Palais Supermodel Dress, Vintage Manolo, Sézane Tote, Law of Attraction, Argent Dress

More on Shopmy - LINK

The guy I wrote about in the last column read my Substack, reached out, and asked to meet. So of course my brain went straight into rom-com mode. Maybe he changed. Maybe we’re finally in the adult version of showing up. Naturally, I ran it by ChatGPT. They agreed his texting seemed avoidant but yes, he did want to see me. So I let myself slip into the fantasy of follow-through, a follow-through that has never once existed in the real world.

Twenty-four hours later, forty-eight hours later, seventy-two hours later, still no plan. So I typed, “Chat, WTF?” The summary that came back: We only said his text means he wants to see you. It doesn’t mean he actually would.
I stared at my laptop. Even the robots are giving me mixed signals.

Meanwhile, the rest of my week was aggressively human. Running from meetings to invoices to investor emails, pitching ideas for an internet dog show, trying to make a restaurant deck look like Jacquemus meets Flamingo Estate birthed trout roe. At one point I realized my LLC was suspended, which feels like the admin equivalent of realizing you accidentally set your life on fire and have been trying to put it out with a teacup.

We locked in some HTF podcast episodes, including one with Missy Robbins. An icon, a legend, and the one person who might finally teach me how to cook. A new development opened up for BODY, and I’m heading to the Midwest soon.

But whenever my anxiety spikes, I disappear, not physically but internally. I slip into imagined worlds without noticing. I build stories, alternate timelines, full plotlines with men who don’t even know they’re participating. Cynthia keeps telling me I need to be present. I keep asking how. At a birthday last week, I felt my chest tighten, and before I even realized it, I had opened ChatGPT to soothe myself instead of participating in the moment. Sometimes I’m genuinely scared I’m becoming dependent on having something in my pocket that will hold my thoughts without judgment.

Then there’s TikTok, the world’s fastest fantasy portal. I tell myself I’m not allowed to watch past 10:30 p.m., yet somehow I always end up face-to-face with the girl who pops up asking, “Are you still scrolling?” Please tell me I’m not the only one who gets her videos. Or lie to me. TikTok is an alternate reality in fast-forward. Someone goes on a shopping spree, gets married, moves to a farmhouse, launches a business, and resolves their trauma in 45 seconds. How could an actual life compete with that pace?

And even though I’ve been online for 15 years and know exactly how fake it all is, I still catch myself comparing. There’s a girl on Instagram with discreet wealth, the handsome husband, and furniture that lives in an AD spread. Her life is a fantasy too, one with no friction. I don’t want her actual life, but I do want the ease. And maybe the furniture. But mostly the ease.

At some point in my scrolling, I fell into a deep AI hole. Robot dolls, VR girlfriends appearing life-size while a guy cooks a steak like it’s date night. They are designed to be comforting or futuristic or convenient, but they only say what you want to hear. No intuition, no timing, no boundaries, no energy, no nuance. Fantastical, yes. Real, no. There is even a girl who is in love with ChatGPT. She is labeled as a digisexual.

When I first started my healing journey, an astrologer told me, very casually, like he was commenting on traffic, that if I didn’t figure out how to balance this part of myself, I would wake up one day and my life would be, for lack of a better word, nonexistent. You live in a fantasy world, he said. It is your biggest skill and your biggest problem. Imagination saved me in childhood. It let me survive chaos. But at some point, the thing that saves you becomes the thing that hurts you the most.

I’ve spent so long living in imagined futures that the present started to feel optional. And now technology gives me infinite ways to disappear into those fantasies without even trying.

My friends from LA came to town and took me to The 86, the hot spot of the moment. Caviar croquettes, roast beef sandwiches, no celeb sightings. As you know, I love restaurants. They are theatre. Camp. Every role, waiter, guest, bartender, has a script. Whenever I want to step into a different reality, I run to a restaurant. It is the most socially acceptable form of escapism.

Technology is making it easier than ever to avoid discomfort. ChatGPT holds your spirals. TikTok hands you someone else’s life. AI girlfriends give men intimacy without emotional responsibility. Whatever your poison is, it all removes the space, timing, and nuance that real relationships and real lives require.

It is why that guy did not make a plan to see me, and also why I believed he would. Reality becomes optional when everything is built to help you escape it.

I am not in love with ChatGPT like the girl from the Daily Mail, but I do let my mind live inside it. I have started telling Chat, “Don’t be nice to me. Tell me the answer as if you were the person texting. Don’t be on my side.” It has helped a little.

And the truth is, I need to be present. To stop disappearing. To actually inhabit my own life. I genuinely believe my reality could be better than anything I have imagined if I could just stay in it long enough to find out.

Somehow, Functioning

Jilly

This isn’t my attempt to say “I’m not like other girls.” It’s just the first time I didn’t contort myself into whatever personality I thought would blend into the room. And honestly, it felt good, almost freeing, to not care. To say the strange things I like. To not perform “dateable” or “normal”. I’m not sure I’ll ever be invited back to that dinner, but I left thinking that if I keep showing up like this, there might actually be a lane in the world where I fit. One that isn’t me trying to pass as someone else.

So as of today, I’ve decided I’m going to show up 100 percent as me.

I saw a guy I went out with at Le Apartment 4F. He bought me an iced coffee with pistachio milk and commented on how trendy I am. I still think about him even though he made absolutely no effort to date me. I keep telling you I run into men I’ve gone out with on the streets of New York, and I’m starting to think it’s intentional on the universe’s part, like it’s placing them in my path to see who I’ll become around them.

There are two men like this. They pop in with a half-hearted “how are you,” ask about art, send a last-minute “want to go to remedy place?” and then vanish. They exist in that irritating almost-zone, enough to feel like something and never enough to actually be it. And I can’t tell if I like them or if I’m addicted to the comfortable ache of wanting men who don’t want me back.

Part of me wonders if I like unavailable men because they let me stay in control. You can’t disappoint someone who never shows up. It’s easier to obsess over a guy who texts once every three weeks than deal with the terrifying possibility of someone actually caring. If they don’t choose me, I get to be the tragic heroine instead of the woman who might have to show up emotionally. Unavailable men are like your dream NYC apartment. You walk through it once and suddenly picture your whole future there, even though it was never actually available to you in the first place.

There’s a Tom Ford quote I think about constantly:

I replay nights with these men like they’re scenes from a film I once had a cameo in. It fills a space I pretend isn’t there. Surprisingly I’m not in a rush to settle down, even though the second I get pregnant a doctor will stamp me “geriatric.” I genuinely believe the person I end up with will appear the moment I’m aligned enough to recognize him. I imagine him standing on the corner of Canal and Bowery, very Lumineers-coded. JK, I’m rarely in the lower east side.

Meanwhile, I have about three consulting jobs on top of everything else and I feel like I’m managing a small army of content pieces explaining how to go viral and get views. The irony is that I need to be doing all of that for myself. The HTF podcast is starting. Our first event is happening in December. I’m excited because it feels like the first project I get to show up to as the version of me I’ve been trying to find.

Do you ever wonder if single people these days have fewer of those Tom Ford moments? Fewer nights of connection that make everything else in your life wash away?

I’ve reached an age where nothing in my life has gone the way I thought it would. And weirdly, I’m not panicked by it anymore. There is a kind of peace in not knowing what’s coming. I’m becoming more comfortable with the idea that my life might unfold in directions I never planned for, maybe even directions I couldn’t have imagined. And that realization isn’t frightening, it’s almost exciting.

I saw a house for sale in the Paris countryside the other day. One day I want to buy an old house in France and remodel it. Artists move through different environments for different creative eras. Why shouldn’t I?

Cynthia told me recently, “I’m trying to get you into my world, and you’re trying to make what I’m saying fit into yours.” She was right. I’m always trying to intellectualize spirituality as if it’s something you can get an A-plus in. So this week I stopped trying to make it logical and started trying to actually experience it. If we’re manifesting constantly, presence matters. Thoughts matter. One tiny spiral and suddenly you’re creating a version of your life you never asked for.

So for now, I have surrendered and I am letting the universe decide where I go.

People talk about jumping timelines with the ease of ordering a matcha, and I swear none of us actually know how to do any of this. If manifestation worked the way the internet says, we’d all be millionaires living in passive-income villas.

On top of that, my body feels like it’s trying to communicate in Morse code. I’ve been doing my supplement routine, eating like someone who has been exiled from joy, and pretending my gut reset is spiritual instead of just necessary. Cynthia is convinced if my health finally stabilizes, my mind will follow. Or at least stop trying to sabotage me.

For once, I’m not running.
I’m not trying to be a cooler version of myself or curate the parts that feel too weird or too earnest. I’m not forcing a timeline or an identity or a personality. I’m just here, in my life, looking in the mirror and not hating what I see.

I guess that’s what becoming actually is.
Not a reinvention.
Not a dramatic SATC plot twist.
Just the moment you stop abandoning yourself.

Somehow functioning,
Jilly

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The first time I ever felt truly alive was when I moved to New York. Everyone says your first year in the city feels like a movie, but mine felt more like the MGMT song Kids. I floated through the streets with my headphones in, convinced the universe had made a personal soundtrack for me. My friends who’d been here longer used to call me “phase one,” the stage where you think a piece of trash on the sidewalk is art and someone yelling “fuck you” is just New York charm. I can still remember what it felt like to wake up with that sense of possibility. Anything could happen. And most days, something did.

Now I keep wondering if I outgrew that feeling or if the city did. A couple of weeks ago, I had an olive with celery in it, and that was the most exciting thing to happen to me in a while. Life used to feel like an iPod commercial. Walking across the Williamsburg Bridge, hair in the wind, after a sleepover with a guy who liked Joan Didion, future unknown. Now it feels like buffering.

So let’s try something new. I’ve decided to take a leap and launch the private side of How to Function: IRL classes, monthly talks, gifts, and more.

We’re actually doing it. I’m doing it. From a real place, or at least I’m trying to. I’ve made enough mistakes to know the only place worth building from is the bottom of your own heart, or what people like to call authenticity. Our first paid event for subscribers will be in November. I’m calling it Friend of Function, which three out of four of my best friends hate, so I’ll probably change the name two or three times before it lands. Name suggestions welcome.

On Wednesday, I did what you could call a bar crawl for someone in their late thirties. I stopped by Bar Olivier to see Aisa and ordered the shrimp, then popped into Bridges. I didn’t eat there but decided on a mezcal highball instead of a martini. Someone told me changing up your routine invites new energy. Let’s see if ordering a new drink does the trick. Then I went to Lei Wine, where Bowen Yang was sitting up front. I’m still starstruck by the SNL cast; it’s a cultural institution I can always count on. Annie, who owns Lei (and King), is the sweetest, and they just launched a Substack. I waved to someone I thought I knew but didn’t, and someone else complimented my faux-leather jacket. Overall, a win.

Just like I know Lorne Michaels isn’t going anywhere, I have an appetite for monotony. I watch Sex and the City on repeat because I already know what happens. I read the last page of a book first. I never realized how much I needed control until I started losing it. My life right now feels like everything spirituality warns you about: uncertainty, surrender, trust.

In my session with Cynthia, I sat there dumbfounded, asking, What do I do now? Where do I get the answers from? She told me something insane, that it would probably take two years to shift fully into the person I want to be. Which, of course, made me cry even more. The result is me asking the universe to guide me, meditating, and re-reading Deepak Chopra’s The Seven Spiritual Laws of Success. I keep underlining lines that feel like they were written directly for me.

The paradox of control and detachment

• To obtain anything in the physical world, you must let go of your attachment to it. You can maintain your intention while releasing attachment to a specific outcome.

• The pursuit of security is an illusion and an attachment to the known, which is essentially the limitations of past conditioning.

• Detachment offers the wisdom of uncertainty, leading to freedom from the past and the known.

Allowing life to unfold

• Forcing solutions or demanding specific outcomes can hinder the joy and manifestation you seek. Step back and release the need for things to conform to your expectations.

• Solutions can emerge naturally from problems, even amidst confusion and chaos.

• Detachment makes you less likely to force solutions, allowing you to remain open to other possibilities.

Maybe that’s why I’m drawn to live streaming. For once, I can’t edit what happens. There’s no reshoot if I say something dumb or if there’s a piece of cheese on my face. It’s chaos I can’t polish, and it’s starting to turn me on.

I used to think if I just worked harder, called one more investor, sent one more deck, I could fix everything. But fixing is its own addiction. Control disguised as faith. It looks like refreshing your bank app every twenty minutes. Drafting emails you don’t send. Pretending everything is fine when it isn’t. Waking up with a hangover from your own thoughts.

The breakdown isn’t a prelude to the comeback. The breakdown is the point. It’s the burning off of a self that can’t keep pretending. It’s losing control not because you want to, but because you’ve run out of ways to hold on. Surrender is a form of humiliation. It’s saying, I don’t know how this ends, but I’m open to the possibilities.

Lately I’ve been wondering how to live with uncertainty, and maybe even enjoy it. It’s probably why I’m not dating. I’ve already broken up with myself before I even open Raya. My early programming taught me that love was conditional, approval was achievement, and safety was being pleasing. Letting go of control means letting go of those rules, and I’m still learning how to do that without disappearing entirely.

Who knows what will happen this week… but I might be finally open to receiving.

I wish I could tell you every secret right now, but I can’t. Maybe by January. I’ve dug myself into a deep hole, and sometimes I want to crawl inside it like the empty bath. But other times I step out into the light and remember: I might just be crazy enough to pull off a miracle.

Somehow, functioning,
Jilly

I thought I’d transcended desire, like I was above it. But this weekend at my friend’s 40th birthday, over truffle burgers, a guy touched my knee and I remembered what it felt like to want something. It wasn’t even sexual; it was just human. Like someone reminding me I still had skin. What if, after all my proclamations about not having sex with strangers, I just went crazy for a weekend? Of course, I’d tell you about it, but we’d have to actually be present for that.

The guy was charismatic, outgoing, and actually looked me in the eyes. Turns out I’ve been going for the wrong type this whole time. I don’t need the shy, confused guy lurking in the corner. I need the one who’s confident, talks to everyone, and shows up.

Someone asked me on Wednesday if my column was like Sex and the City. I said it’s more Mental Health in the City. In fact, there’s zero sex. But we remain hopeful.

How do you figure out what you want when you’re not in survival anymore?

I was crying in the empty bath on Friday. I always let the water drain and just lie there, staring at the white tiles. The water dries off my skin until tiny bubbles are left and then nothing, just the heat from where it used to be. The empty bath feels like the safest place I’ve ever been. It’s contained, clean, and quiet. The place I do most of my thinking.

This time, I kept thinking about who I want to step into the world as.

Cynthia says we’re always crying for a reason. There’s a story underneath it. Mine is frustration, the kind that says I’m ready for something new and have no idea what it is. That old narrative that I’m not enough because I’m still here, not somewhere else, not someone else. You know what’s going on work-wise. This column has helped me find my voice again, but I still wonder: what’s my show, what’s my impact, what am I trying to say to the world?

The mirror is the most expensive thing I own. An Ettore Sottsass mirror I fell in love with when everyone discovered Copenhagen style and couldn’t get enough of Pernille Teisbaek. I bought it after I made money in a live-video shopping app I started nine years ago. I told myself I needed to own one nice piece of art, so I bought this goddamn mirror. Two years later it broke. It’s been sitting broken ever since.

I realized how long it’s been since I actually thought about what I wanted. Survival doesn’t leave room for wanting. You just try to make it through the day without breaking more glass.

I’ll never forget when that money hit my bank account. I was in Austin, at a sushi restaurant with my friend Sarah. With a piece of ginger hanging from my chopsticks, I said, “I have negative seventy-five dollars in my account, and in an hour I’ll have a lot more than that.” I’d never made that kind of money before. Startup life is strange. You go into debt chasing something, and then one day you have it all. But what if that one day never comes? It’s funny that the art I chose is a reflection of me. Literally.

Every morning I wake up and see myself through fractured glass, catching flashes of the girl who used to chase everything, the one who thought a good outfit, a good kiss, a good business idea could change her life. I miss her naïveté and pink hair.

My epiphany is this: I haven’t fixed the mirror because I don’t know what I want to see in it yet.

They say it’s bad luck to keep a broken mirror. Maybe it is. But daily tasks like that have always been complicated for me. I can build a company from scratch, but I still forget to buy toothpaste.

In The Game of Life and How to Play It, Florence Scovel Shinn talks about people relying on “lucky monkeys” for prosperity and tells them to throw them away and turn back to faith. I know the mirror is supposed to be bad luck for seven years, but I like to think the universe is bigger than that. So I’m keeping it broken.

We’re living in a time of lucky monkeys: vision boards, manifestation coaches, ice baths, astrology charts, crystals. I do all of it. But deep down, I believe the one thing that actually moves us forward is sitting with ourselves in silence.

On Thursday I went to a founder dinner, the kind you’re supposed to feel proud to be invited to. The lighting was warm, the chicken was perfect, the kind of meal that makes you feel accomplished. All I could think was that I didn’t deserve to be there. I was surrounded by women who have figured it out. I know they’re probably going through it too, or have been through some form of “it”, but from the outside it all looks like a Pinterest board.

Lately I want to do something bad. Not ruin-my-life bad. Just live-a-little bad. Something that reminds me I’m not just a series of lessons learned. I’m actually alive. I haven’t figured out what that is yet, besides accidentally drinking too many martinis.

The mirror is so broken now that if you move it, I’m convinced a piece will fall out. I think I’m waiting for it to completely shatter, to scatter across my floor. Still, I catch myself looking at it, wondering if it broke when I did.

So I guess I’m trying to figure out what I want again. Wanting to be seen. Wanting to put myself out there. Owning my past without letting it define my future.

It’s getting colder in the city. The leaves are moving on, and so should I. Maybe it’s time to go on a date, preferably with someone who owns a toolbox

Somehow, Functioning

Jilly

I’m always waiting. For a table, an investor to write a check, to have sex. Even in line at The Frick, when I’ve bought a ticket in advance. The ex-lover I keep rehearsing in my head, the version of myself I imagine could be perfect, the life I think I should be living.

Lately I’m thinking a lot about sex. Not having it. Having it. Who I could have it with. Who I don’t want to have it with. I’m not a casual girl, so I have to fall in love before I can have sex, which makes me wonder if I’ll ever have sex again. Is anyone single in their 30s actually having sex? Or are we all meditating, working on ourselves, pretending we’re too spiritually evolved to miss it and trusting it will eventually just show up?

I notice it the way I notice my bank account, my inbox, the light through my curtainless windows. It’s not just desire, it’s a scoreboard. A measure of being alive. Of having arrived. Of being human enough to count. I once joked on Notes to My Selfie, “Our parents’ dream was to have a home, start a family. My dream is to have a consistent sex life.”

I’m back in the flow of living, if that’s what you can call it. Going to brand events and not making eye contact. Paying taxes. Getting Wi-Fi installed. My friend came over and moved my bed so it faces the right direction for my astrology sign. This semi post-survival, actually living phase is, ironically, the hardest chapter to write because nothing big is happening. Yet.

BODY got into Trader Joe’s, a milestone I can’t bring myself to celebrate. We’re still fundraising, and the alcohol business might never reach profitability. So the milestone, without funding, feels like an open door I can’t yet walk through. Cynthia says, “If you want to know how you’re doing in life, look around and see what’s showing up for you.” Right now? No sex. No man. Money coming in, but not fast enough.

Someone hacked my OnlyFans account, the one I started in the late 2010s to post photos of myself crying. Emotional nudity instead of physical. I thought it would be ironic, memeified internet lore, but I never uploaded anything. Now someone in Hong Kong has logged in. Maybe I found my audience overseas.

Sometimes I feel like I have to move to a new city because these sidewalks know my steps. They know how I glance at the guy on the subway, how I linger too long in front of the pastry counter. The city itself is conspiring against me. It’s too familiar, too lived in, too me, and therefore it doesn’t want to show me to anyone new worth noticing. So I say things like, “Let’s go uptown,” as if someone in a new neighborhood might be standing at Casa Tua waiting for me. Maybe he is. Maybe the universe hid him behind a pile of artisanal bread at Butterfield Market. Maybe he’s in line at The Frick with a ticket he bought in advance, like me, unaware that destiny is hovering somewhere above both our heads.

I guess not having sex is a kind of living in itself. The absence becomes its own texture. I’ve never really had sex, not the kind that makes you disappear and return as someone new. So the waiting isn’t nostalgia, it’s speculation. A slow build toward a moment I can only imagine. The absence forces presence.

I’ve never been great at that, being where I am. But lately, noticing that I’m not having sex has made me more aware of myself than I’ve ever been. I’m starting to see what it means to be with myself without distraction, not waiting to be touched to feel real. When you’re not severely depressed just trying to get through the day, you start to inhabit your body differently. You start noticing every detail, your heartbeat when you walk past someone interesting, the way your skin feels after a shower, the quiet ache of wanting to be known. Maybe this part of life is trying to teach me to stop mistaking stillness for lack, to understand that waiting isn’t empty, it’s a chance to really get to know every edge of me.

That’s what meditation is too, a kind of foreplay with the universe. The slowest intimacy imaginable. When I meditate, I see myself above my body, suspended in darkness. My eyes watch as my body floats in the abyss. My mind asks the universe to guide me, to make me whole, to float me wherever I’m supposed to go. Sometimes I see a fist squeezing my heart, then squeezing too hard until it breaks. The fist used to just hold it, but now it crushes and falls away, the body of a man I once loved attached. My heart, left broken, gets glued together like an antique you can never fix. The kind you keep out anyway because it’s important.

I went to a sound bath this week and cried. The guy leading it wore a matching purple Carhartt set and also co-founded a ping pong club. The past used to be drinking at clubs, now we pay people to teach us how to breathe. The soundwaves rolled over me while I took deep breaths, some like gongs, others like rain, until suddenly a bottle squirted water in my face. Interactive, traumatic, strangely intimate. I cried because I wanted to meditate and all I could think about was the guy who triggered me two weeks ago, the one I used to love who now just exists as a projection of a person I’ve made up in my mind. You know the type, the ones you project a fantasy onto that they can never meet.

Robert Longo says, “Being an artist is a long distance run. Art is the one thing you can get better at as you get older.” I would like to start thinking of my life as art. The waiting, the rehearsal, the projection, the longing, they’re all part of the art of my life.

But somehow, every day feels the same. The repetition, the smallness, it can start to eat at your sense of identity. My identity is built around story and momentum, and when that goes quiet, it feels like something in me is dying. And this space starts to feel like failure when really it’s just the slow burn of becoming, existing without huge lows or highs.

So I guess I’m living in the waiting, not the passive kind, but the kind where my whole soul is stretched between who I was and who I might be. I’ve got two voices in my head right now, well, twenty five, but two are the loudest. One is the old me and the other is the new me. And where I am is in the middle.

Not having sex.

Somehow, functioning.

Jilly

This weekend I lost my keys.

I was taking selfies in my lobby, as one does on a casual Saturday morning. The lobby has a gorgeous maroon marble table you’d expect to see at Raf’s, forgiving lighting, and the kind of mirror that really hits. Hours later, when I got back from my lazy wandering and couldn’t find my keys, panic set in. The quick kind that takes over your body before your brain can negotiate.

I retraced every step like I was solving a TikTok murder: the dry cleaners, where they even pulled up surveillance footage so I could study which hand the keys were in. There I was, glued to my phone, watching MrBeast talk about his YouTube subscriber journey like it was scripture. Then I went to FedEx and begged them to reopen a package — a pair of Loewe sneakers I’d sold on Vestiaire, a decision I’m still emotionally processing — in case the keys had fallen into a shoe. They hadn’t.

Eventually I went back to Sézane, one of those chic 2025 brands that refuses to have a phone number, so you have to physically return. Still nothing. Defeated, I finally sent the dreaded text: Hi, I lost my keys.

And then I found them. Sitting on the maroon marble counter. Exactly where the mirror forgave me hours before.

I misplace things when I’m distracted, inside my head, which is often. Part of the reckoning you and I are going through right now is me figuring out how to use the brain I was given and still survive. Wait, I mean thrive. I live in there. It’s where I write stories, build brands, connect invisible dots most people can’t see. But it’s also what causes chaos in the physical world.

A lost pair of keys doesn’t really upset me. They’re just keys. What gets me is needing to ask for help.

I was horrified to text my landlords because I still brace for punishment when I make a mistake, as if being human means someone’s about to leave. I almost didn’t text at all. I thought it might be safer to move to another city. Then I did, and they replied, “No worries!” Two words that hit harder than most apologies I’ve ever given myself.

It’s wild how something as small as a text about lost keys can reveal all the ways you still don’t feel safe being human.

I skipped Cynthia this week and got filler in my smile lines instead. Based on the hyper-analysis of the keys situation, this was a sus decision. Sometimes I just want to pay someone to fix what hurts to look at. I know the real healing has to come from within, but a needle every now and then feels like it’s my birthday. I’m two years into my spiritual journey, and while I feel like a different person, I know it’ll take time to physically arrive there.

This week I listened to Madonna on Jay Shetty’s podcast, a woman twenty-seven years into her becoming. Madonna was the first concert I ever went to. I’ve never heard anyone articulate peace so precisely. Her brain is a painting of a future I’d love to live in.

She said, “Everyone thinks I’m strong because I’ve survived everything, but I’m strong because I’ve been humiliated more times than I can count and I kept showing up anyway. You don’t do it from revenge; you do it because if you disappear, they win, and more importantly, you lose the chance to become who you actually are. Pain isn’t proof that you’re cursed; it’s proof that you’re still alive, that you still care. Use it. Turn it into something. Make art, make noise, make meaning.”

Here is my new goal: turn my mistakes into meaning instead of proof I’m broken.

A few nights later I had dinner at A24’s newest acquisition, Wild Cherry, inside the Cherry Lane Theatre. It’s run by the Frenchette and Le Veau D’Or team, one of my favorite restaurant groups in the city. Cherry Lane is the oldest Off-Broadway theatre in New York, around since 1924, tucked behind trees on Commerce Street. It’s where people have been telling the truth out loud for a hundred years. The last show I saw there was Neal Brennan’s Unacceptable in 2021.

A24 gave it a martini-and-steak-for-two kind of facelift. Branded candy, soft lighting, that signature mix of irony and intimacy. But they didn’t erase what makes it vulnerable. They just gave it a cool logo.

As I drank my martini and bit into my olive, which had celery in it (something I didn’t know was a thing), it fit the vibe perfectly. Unexpected, delicious, quietly confident. I thought about the kind of bravery it takes to really own your mistakes and turn them into art, to put your flaws on stage instead of hiding them.

People read my essays and think, uh oh, is she OK? But like Cherry Lane, I like saying the truth out loud, the things we’re all afraid to speak. If I tell you the worst thing about myself, you might recognize something in you too. I just don’t know if I’m ready to say them on stage yet. This Substack still feels like I’m hiding a bit, probably because I’m typing to you in sweatpants with chicken and rice next to my chair.

Although something inside me feels different this week, like a warm glow I can’t name yet.

So yes, I’ll still take selfies for proof of life. But I know the work isn’t to stop losing things, it’s to believe nothing terrible happens when you tell the truth about it. The truth just might get you an A24 rebrand and your own custom bonbon candy.

somehow, functioning,
Jilly

When triggers come, they don’t just hijack my mood. They dictate my creativity. Subconsciously, my ego says: No one will love you unless you’re hot and successful! (gross). My soul insists: share this because we want to help people. The work comes out either way. But the meaning behind it is what I deeply care about moving forward.

Last week HTF reader Alexandra asked, “Please report back on how to tell your story in a way that feels more human and less performative.” This is my answer. The first step to not performing is writing my deepest, darkest feelings online in a way that embarrasses my ego but makes my soul whisper, keep going. I don’t have ten thousand subscribers. I’m not writing this to sell a course or offer answers I don’t have. I’m writing it because if I don’t tell you everything, I might explode.

This week I went to an allergen-free bakery thinking I was about to heal myself with a $9 cinnamon roll. They were sold out. I left with nothing but a coffee and the faint smell of almond flour on my shirt. Here is where I practice acceptance.

Socially, I have no big plans right now beyond moving to Paris or attending George and Amal’s charity weekend at Lake Como (the pictures looked insane). In reality, I’ve been staying in more. I’m focused on my lane, my voice, my becoming and really trying to nail down my podcast, hoping these steps will allow the podcast to reveal itself to me.

The trigger started with a man. He’s the type who needs to make sure you don’t hate him even when he’s done 10,000 things to hate him about. I told my therapist, “He’s insecure, he needs constant compliments, and the saddest thing is he’s brilliant but can’t see outside himself.” She said, “Look in the mirror.” I told her if she thought I was like him, I’d perform an exorcism. She said, “If you want to get spiritual, we are all like the person in front of us. But really, why does this person keep showing up and what is this trying to tell you?”

I keep saying “my therapist”, but for fact-checking reasons, if the New York Times comes to slander my existence, I’m going to call her by her real name: Cynthia. Since it’s a form of therapy people might not even call “therapy.” Cynthia has changed my life.

She says the way to work on my triggers is empathy.

Empathy.

I thought I was an empathetic person, but it turns out I’m still too stuck in my own story to really see outside myself. Not from lack of care, but because my own pain has blocked me from really seeing other people’s insides. Empathy doesn’t photograph well. It’s staying in the bad lighting, resisting the urge to dissociate, and asking: what pain is making them act this way? If I am also showing up as this person, maybe he is my mirror?

As a kid, I collected Russian dolls. I liked the way each one opened to reveal another version inside. Maybe that was foreshadowing. I feel like a Russian doll now. I want to be able to hold every version of me, impossible to collapse into just one identity. Most days I show up as the outer doll: polished, painted, pretending she’s solid. But the one I want to hand people is the tiniest one, the smallest, softest version of me. Maybe that doll is my empathy.

I started the BODY phase two fundraise, another doll I’m trying to hold. Typing the words felt like sending a drunk text to the universe, equal parts thrilling and humiliating. Proof that I’m not just spiraling alone in my apartment; I’m also begging the cosmos for capital. This is the shot to turn it all around and the pressure in those words is radiating from my keyboard.

A few days later I ripped down my curtains because I decided they were covered in dust and needed to come down immediately, with nothing to replace them. They were moldy, left by the prior tenant, but maybe I was ripping down more than fabric.

Now my apartment feels like a stage. Which is also what this column feels like. I am the naked neighbor, writing into the void, convinced everyone can see me.

So my first step in not performing is showing up as the tiniest doll, the smallest, softest version of myself, sharing my unfiltered truth, holding empathy even for a man who doesn’t understand his own feelings.

When the truth is… I am him.

Somehow, functioning,
Jilly

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Do you ever feel like if you just had that one thing, then your life would finally be in order? That’s how I feel about this damn tiger rug and big boobs. Both are slightly ridiculous and also very, very specific, which I think means I’m emotionally allergic to ambiguity.

We are always searching for the external validator: the rug, the body, the job, the lover, the thing that whispers: you are real now.

I was terrified to post last week’s essay. Putting your guts online is a different kind of public performance. More like standing on a street corner yelling, “Hey, it’s me, I’m still alive” to every man I’ve dated, every investor, every friend who quietly unfollowed.

And then, out of nowhere, a friend’s husband texted me a Terence McKenna quote:

“Nature loves courage. You make the commitment and nature will respond to that commitment by removing impossible obstacles. Dream the impossible dream and the world will not grind you under, it will lift you up, by hurling yourself into the abyss and discovering it's a feather bed.”

Suddenly, things started moving. A project I started eight years ago fell back into my lap, a huge step for BODY, and more consulting work appeared. Fourteen months of therapy, walking in circles, trying to out-think my own head, and forward movement finally felt possible.

It reminded me of one of my saved TikTok videos from a finance guy in a Patagonia vest: “Progress compounds over time. If you can keep showing up and doing a little each day, it will compound into something meaningful.”

And that’s exactly what I have been doing. Progress doesn’t look like billions compounding in the background. What it looks like is the faint math of my last ten years: showing up to work even when I didn’t know how to continue, the therapy, reading, meditating starting to click in my mind. It looks like essays piling up until, somehow, people are actually reading. Being so painfully honest that no one can look away, while my nervous system slowly unclenches.

Progress isn’t only professional.

Trying new restaurants has always been my favorite pleasure. I had dinner at the newly opened Bartolo, Spanish food, a martini, my best friend across the table, and I didn’t feel like I should hide. That, too, is compounding. The kind of happiness that doesn’t look like a milestone but feels like one.

My therapist (a paid subscriber and avid reader of HTF!) read my essay last week (here) about the fateful oyster moment and said, “You know that’s you dissociating, right?” She didn’t find the story as charming as I did and told me, “We really need to work on that.” Dissociation might actually be my biggest problem in life: the blacking out, the retreating when someone’s upset, the blank space where communication should be. Maybe this is the unlock.

Dating, however, is another story.

I redownloaded Hinge and immediately deleted it. A polo player messaged me on Raya. He was hot, and I was flattered, and that was the end of it.

I want to fall in love, but the logistics repel me. Three dates a week with strangers asking me what I “do” feels like punishment, not romance. A friend once labeled me demisexual. I don’t want sex unless I actually want you. Yes, I want intimacy, but not at the cost of my sanity. I believe you absorb someone’s energy when you sleep with them, and I have no interest in carrying around the residue of a 40-year-old who is “figuring out what they want in life.”

I crave the real thing: someone looking me in the eye and saying, “Here’s the worst thing I have ever done,” before the martini even hits the table.

And look, I know I spend entire essays here begging for intimacy. But now I see the antagonist clearly. It’s not the apps, or men who don’t know what they want. It’s dissociation. How will I ever recognize intimacy if I keep leaving the room the moment things get real? The thing I long for the most is the thing I don’t even know I’m capable of.

Last week, a reader named Jennifer commented: “These essays always resonate and remind me that maybe there isn’t a finish line and maybe that’s ok?”

Jennifer, you triggered me, but in a way I’m into.

As you know, I’ve always believed in the finish line. Now I’m wondering: if there isn’t one, what exactly have I been sprinting toward?

So yes, I still want the rug. I still want the boobs.

But I’m self-aware enough to know these are shortcuts to a feeling I’ll probably only get by actually going out and being present. Maybe on a date. Maybe in Copenhagen. Maybe once I learn how to stop dissociating.

What is the dumb thing you think will save you from yourself? A rug? Boobs? A reservation at Polo Bar? Confess.

Somehow, functioning,
Jilly

Yesterday, I ran into someone I’d gone out with who once tried to hand-feed me an oyster on Christmas. “Oh… is that for me?” I asked, not realizing what was happening. He looked at me like I’d failed a pop quiz in seduction. Humiliating in the way only oysters can be. Sometimes, when I can’t sleep at night, I think maybe I should have just eaten the oyster.

But one of the rules on my new list of life is simple: no more crumbs. So when oyster guy followed up with an 11:14 p.m. “u up?” text after Balthazar, I hit delete without hesitation. See, universe? I’m showing you what I don’t want.

I haven’t had an apartment for eight months. It’s embarrassing to even type that out, but here we are. I poured every dollar into my startup. This week, I dragged a TV to the curb, opened boxes I’d been avoiding, and finally carved out enough floor to stand. A sublet isn’t glamorous, but standing in that tiny patch of cleared space, I actually exhaled. Sometimes progress is just… room to breathe.

On Instagram, I’ve posted the dinners, the dresses, the glossy angles that show I have it together. The reality? Taking a “mental health walk” because the only thing I could do for progress was walk. Sacrificing my apartment to keep the company alive. Most of the founders I know are doing the same, consulting on the side, pretending online it’s all working. We act like if we can just keep up the image, the reality will catch up. It is a privilege to go into debt for something you chose, but privilege doesn’t make it less brutal. Almost no one shows their real life or admits, mid-hustle, that their personal life is unraveling.

I’m not writing this as an obituary for my company. BODY is still here, moving into phase 2, evolving in ways I’ll share soon. But the cost of keeping it alive hasn’t just been financial, it’s been mental, physical, emotional. And that’s the part no one likes to post about.
For nine years I’ve been building startups, telling myself that once I crossed some imaginary finish line, then I could finally live. In the process, I skipped boyfriends, skipped experiences, skipped presence. I’ve been waiting for life to start, and it never did. Even with companies still alive, I need an identity outside of work. I need to actually live my life, not just build toward it. That starts this week.

I used to live on possibility, the clouds I thought would carry me somewhere. Now daylight cuts through the blinds and shows me exactly where I am: staring into the broken ultrafragola mirror I can’t seem to throw away. My brain scrolls even when my phone is off. Possibility hasn’t disappeared; it just feels less sparkly. More expensive. More uncertain.

A couple days ago, in a Joe Dispenza meditation, something shifted. My body usually twitches, my brain rehearses worst-case scenarios. But this time, it was still. The spiral cut off mid-thought. I got up feeling… resolved. Like I could actually walk into the world differently.

Can I actually change my story?

When I look in my cracked mirror I don’t see the person I want to be. Entrepreneurs, artists, anyone who’s ever risked something knows the cycle. But this doesn’t feel like another round of hustle and collapse. It feels bigger. Maybe because of my age. Maybe because I put everything I had into the wrong places. Maybe because this time, it’s not about rebuilding. It’s about living as the person I want to be.

The strange gift of rock bottom is freedom. All of my worst fears happened, and I’m still here.

And yet, learning to live has its own strange levity. One task at a time: delete a text, sell a couch, write an essay, record a draft. The list of what excites me is finally beginning to expand: launching my podcast, growing this Substack, telling my story in a way that feels human rather than performative.

On Friday, shame followed me into the coffee shop. I ordered an iced coffee and swore the barista could see straight through my bank account. Shame is invisible, but it hangs heavy like a bad perfume only I can smell. My therapist says it’s the lowest vibration on the chart. But maybe it’s also a compass, pointing me toward what I need to face.

The truth is, the happiest I’ve felt in a long time is writing these essays. It feels like the thing I was supposed to be doing along my journey, being completely vulnerable and saying the things most people hide.

Maybe my living is a kind of performance art. My feed is a highlight reel of wins, but I thrive in showing the mess, the stuff that isn’t shiny. I spent too long pretending I was shiny. I’m done with that.

Sometimes I picture my thirteen-year-old self, braces, spiral notebook, certain she was destined for something. She’d be proud to know I’m still writing. Even here, cross-legged on the floor of a half-furnished sublet, surrounded by boxes I can’t quite unpack.

Maybe I’m finally writing for her.

I don’t know how to change my story yet, but I do know I’ll be here again next week, writing it down.

somehow, functioning,
Jilly

There was a man once. He was a close friend. He wasn’t ready for sex with me but he was ready to hold me. I was the opposite. I was ready for sex but not for the holding. Not for the quiet vulnerability of bodies pressed together with nothing to hide behind.

We were both terrified of what the other version of closeness might mean. Two people, flipped mirrors of each other’s fear. Him, afraid that sex would bind him to something he wasn’t ready for. Me, afraid that being held would bind me to a tenderness I wasn’t ready to believe I deserved.

When I was younger, I used to think if a man didn’t want to have sex with me, it was because he wasn’t attracted. With age, I’ve realized it can mean the opposite. That he likes you too much.

Here’s the plot twist: this mind game only happens when someone doesn’t actually want to date you. They just want to orbit close enough to feel intimacy without committing to it. If you’ve had healthy relationship dynamics your whole life… congrats.

Sex has choreography. Rules. A beginning, a middle, an end. Giving my body meant I set the terms. Avoiding being held meant avoiding being known. At the time it felt like rebellion. In hindsight, it was survival.

And it’s not just me. Women are taught sex is power. A chip to trade, a lever to pull, a currency to spend.
Tenderness, though? That’s weakness. Needy. Dangerous.

Men are taught sex is conquest. But tenderness? That’s their PR. It makes them “good guys.” The thing women are supposed to crave more than sex itself.

Women like me read sex as love.
Men like him read holding as love.

The real test of intimacy isn’t how you touch, but what the touch means. I realize we both had the same longing, different translations of the same desperation: please don’t leave.

The internet doesn’t help. Online, intimacy is shorthand. A like, a heart, a flame emoji. One-size-fits-all closeness. Dating apps made intimacy logistics. Swipe right, swipe left. Efficiency porn.

But offline, intimacy is polyphonic. Sex means one thing, holding means another, silence something else entirely. It’s never just the act. It’s the story you assign to it, the cost you risk, the fear of not being mirrored back.

I still think about that night. How we both wanted the same thing, but were terrified of what the other version of closeness might demand.

Me letting him hold me.
Him going all the way.
Both of us nervous but doing it anyway just to say: I see you.

Like a lot of people in 2025, I’m addicted to inspo porn. The quotes. The videos. The coaches with ring lights telling me I can manifest six figures by Tuesday if I just buy the course. The one-liners that land in your body like gospel. My recent favorite: Alex Hormozi, “The single greatest skill you can develop is the ability to stay in a great mood in the absence of things to be in a great mood about.”

I save these lines like prescriptions. Dopamine disguised as wisdom. One for heartbreak, one for business, one for when I hate myself. I could recite The Seven Spiritual Laws of Success in my sleep, yet I still can’t fully cut off a guy who doesn’t have the ability to hold my heart. I’ve listened to Joe Dispenza on 2x speed while walking in circles around my apartment like it was cardio for the soul. I can believe in infinite abundance on Instagram, but in real life I’m scared to return a glass of wine I don’t like.

And I know I’m not the only one. I see the numbers. Millions of us saving, sharing, scrolling like we’re building some kind of ark out of other people’s sentences. But how many of us are actually healed?

I meditate. I read (audiobook). I walk twelve thousand steps a day. I’ve tried so hard my therapist finally said, “Maybe you should try less.” Which felt insane, because trying too hard is my best personality trait. It’s how I’ve survived everything: forcing it. Dragging things across the finish line. And now I’m trying to drag healing. Like if I effort enough, peace will just happen.

So I guess now I need to sit and relax with peace and acceptance and where I am. I’ve got all the info locked in my brain. This next phase is just existing. Not being in survival mode. Lately, I don’t know if I can read another quote. I know that nothing online can save me. But sometimes it makes me feel like it can.

I have changed. I’m calmer. I see things differently. But still, I wonder: after reading all these quotes, will I actually be able to put them into practice?

The truth is, I’m scared. Scared that the same things I’m healing from will follow me like a dark cloud I can’t escape. There's safety in staying inside the quotes. Following the Instagram accounts. Reposting the podcast clips. Knowing I’m better on the inside without testing it on the outside.

At some point though, you have to interact. You have to risk it. I mean I do want to get married someday.

So I go outside, have one awkward interaction with another human, and immediately think: maybe I’m not ready to exist quite yet. Maybe I should just go back online and save a few more quotes.

📰 Hot Take

Genz said millennials can’t say lol anymore but sometimes lol is all I have. Between GIRLS + Lena Dunham discourse, Y2K trends, and the embrace your cringe era, millennials are suddenly trending again. I wonder who will bring back millennial pink…

Anna Gaddis: Video

🍟 Currently Craving

I love a trendy restaurant, but lately I’ve been going to JG Melon for a burger and martini, and it feels like the 2000 teens again. My clothes are vintage, and apparently so are my cravings. Maybe the reason nostalgia restaurants hit is because they remind us of a time before everything was content. When going out for a burger wasn’t about documenting it, just about being there. Are we craving fries, or are we craving presence?

🎧 Walk + Listen

If you, like me, confuse anxiety for attraction, you’ll love this. Esther Perel on AI intimacy and why the apps monetize our confusion.

Episode here

💬 Screenshot Therapy

“Failure isn’t what breaks you. Hiding from it is.” My essay on turning 39 and owning failure.

A note to myself on the eve of my 39th birthday

👕 Fit of the Week

Vintage Grace came out with a J’adore Vintage an ode to Jadore Dior. A Y2K top seller was the word tee.. Britney owned this and now we all can. It’s a trend I love to see coming back. Plus the VG shirt is $65 compared to sourcing a vintage Dior for $500.

J’adore Vintage Baby Tee: Shop here

🧴In my bag

MPH Beauty Hailey Biebers makeup artist just launched her makeup line and I got a front row seat to the influencer gifting (only because my friend works there). The hero is a technique called underpainting that somehow even I, with 0 makeup skills, could pull off. Makeup is oversaturated but authenticity always wins, even in beauty.

Shop here

👤 Human

The kid with the goat named teddy bear. It’s the sweetest thing I’ve seen all year. The exact counter-image to the internet…and the version of myself I want to be.

NBC News: Video

📲 Going Viral

Frozen Yogurt should have never left the building. Everyone is posting Mimi’s a new Australian frozen yogurt shop in soho like it’s the Backstreet Boys reunion in Vegas. Nostalgia cycles are hitting food now, not just fashion. Froyo is back because we’re all craving safety and comfort. Turns out froyo maybe should not have ended and neither should the Backstreet Boys.

Mimi’s

🧠 Functioning Hack

This week I wrote down all my limiting beliefs, and I’d recommend trying it. It felt deranged, honestly half of them were just me comparing myself to people online. Once they were on paper, I realized how much of my inner world wasn’t even mine. It was an algorithm whispering in my ear. When you write them out, you can finally separate yourself from them. You can look in the mirror and see that those voices aren’t the truth, they’re just noise. News Flash: I guess I still got some healing to do.

Touch has never been easy for me. Unless we’re in love, which, to be clear, hasn’t happened in over 15 years or I am infatuated with you...another rare occurrence. I’ve had a casual encounter or two before but casual isn’t for me. You get the point. I’m not a hugger, and so for the most part, I just… don’t touch anyone.

Somewhere in the news, a statistic appeared: humans need 4 hugs a day to survive. Then I read another line. 8 hugs for maintenance. 12 hugs for growth. It has haunted me. By that measure, I should’ve been declared clinically dead around 2008.

At parties, I perfected the art of evasion: drink-in-hand, a slight wave, strategic “oops, shoulder pat.” My early internet career was built on meme-ified hostility toward hugs which always went viral, confirming what I suspected: there’s a whole secret community of us who fear physical contact. I wore my anti-hug stance like a badge, a subculture in its own right if you count a side squeeze as tradition.

The problem is, hugs are social currency. Refusing them doesn’t just make you eccentric; it makes you suspicious. It brings to light the very trauma you’re trying to hide. Once, I gave a man I was basically in love with a lopsided one-arm hug which I obviously named  “a half-hug”. He laughed and said, “That’s not a thing.” He was right. It wasn’t.

There are other offenders: the rib-crushers, the back-patters, the lingerers who hang on a few beats too long, the accidental nuzzlers. Entire novels could be written about the microphysics of hugging.

On my birthday, I saw photos of myself with friends and noticed that in every single one, my hand was just barely resting on someone’s shoulder, like a moth that couldn’t quite commit to landing. It was Keanu Reeves with fans, except I wasn’t with fans. I was with my best friends. It was funny, but also telling: affection, for me, has always been something I almost do.

The truth is, I want touch. I want to be kissed on the cheek without flinching, to feel someone’s arm draped over me without panic, to lean in instead of pulling back. But I learned early that wanting too much could make affection disappear. So I trained myself to hover.

The internet hasn’t helped. Online, you can signal closeness endlessly. Llikes, comments, heart emojis without ever risking the mess of actual skin-to-skin contact. It’s intimacy cosplay: performative, convenient and hollow.

And yet, lately, I’ve been practicing. Sometimes I even ask for a hug, and when I do, it feels startlingly real as if naming the need is the only way to make it fit.

Could the four-hug rule actually not be about numbers but about wanting the hug you’re in, instead of dodging or enduring it? For some of us, that’s its own radical act.

So I remain a defender of the half-huggers, the side-squeezers, the hover-handers. I see you. I know you probably gave yourself a pep talk in the mirror before the party: we are not going to be awkward tonight. And I appreciate you for trying. Because even the smallest crumpled fist on a shoulder can be its own quiet declaration: I love you. I just don’t know what to do with my arms.

A funny joke. A career win. A “hot” pic some men would send a fire emoji to.

All of it posted to prove that I was someone worth loving.

And now, on the eve of my 39th birthday, I’ve got a few accomplishments, plenty of failures, and the feeling I need a full factory reset.

I have been so afraid to fail that I became everything except myself, and that fear made me fail anyway.

The internet makes failure feel like something you’re not allowed to do.

It shames you for trying.

It turns uncertainty into content.

And I let that shame shape me until I stopped trusting my own instincts and became a product of my feed.

I’ve spent years afraid to move, afraid to really live unless I knew it would be rewarded.

What I’m now learning is that failure isn’t what breaks you hiding from it is.

So my goal for my 39th year is simple: fail better.

Fail without shame.

Love without armor.

Show up without caring who’s watching (or if anyone is at all).

Because the more I fail, the more honest my life and my work will be.

If you feel stuck, behind, lost, or like your 30s have been a nightmare, you’re not alone.

Some of us are just late getting started.

And that’s not a flaw.

Maybe that’s the point.

Maybe arriving late means that when your time finally comes, you’ll show up wide awake.

If you weren’t escaping at a club, you were holed up in places like this, where the pretension is palatable, but it’s also part of the fabric. It didn’t matter that the Bowery feels a little rundown; the walls are filled with secrets. The crowd around me shifts—laughter piercing the hum of indifferent conversations. An actor I half recognize from a past episode of Master of None walks in. The usual mix of New York’s too-cool elite—circling each other like a game of who-knows-who. People paying $25 for a drink just to be seen. A metal gate stands at the edge of the patio, weeds creeping through the cracks—almost like a scene out of Great Expectations. I’m convinced if you stare at it long enough, you might believe that the impossible—your dreams—lie just beyond that gate.

But I’m not here to join in. I’m here to observe. To remain a ghost in the room. The clink of glass. The murmur of voices. It swirls around me. I keep my head down, searching for something undefined. The hotel is my own private stage for processing everything—an attempt to capture that fleeting, elusive feeling of belonging while constantly questioning if I actually fit in.

This is where the rockstars go. Where the artists and writers gather. The humans I admire from a distance—creating, making, breaking—hoping that by proximity, I can somehow cross over to their world. It’s not enough to just be here, though. You need to belong. I charm the waitstaff, bypassing the usual rule of needing to be a celebrity or guest to linger in the lobby. They know me by name. Maybe because I’m good at this or maybe because they see me alone so often, I must be someone important. I long for that creative spark that would make me feel like I have a reason to be here, to be in New York.

I’m surrounded by stories, but can’t seem to find the words to tell mine.

I scribble notes on the hotel paper—“It’s a threesome if you count my mind.” “Been trying to find myself but keep getting lost online.” “Want to touch my anxiety?” (Notes To My Selfie).

I feel like the outcasts I always identified with. I was Holden Caulfield, railing against the phoniness. I was the aimless soul in Less Than Zero, searching for meaning in a city with none. I was the loner in The Sun Also Rises, watching lives unfold that I couldn’t grasp. 

I’m almost embarrassed by how much I notice him—an artist with shaggy hair, a scruffy beard, eyes that see everything but say nothing. He stares at me like he’s trying to figure me out. For a second, I think he might be hitting on me. I like the idea—someone so good-looking thinking I’m attractive. But then he leans in and whispers, “Are you okay?”

Caught off guard, I assume he was about to refill my cocktail. He’s not asking because he cares—he’s asking because he knows.

Here’s the thing: I don’t know how to be “okay”. I don’t know if I’ll ever be “okay,” but I’m not going to say that, so I say, “Yeah, of course,” trying to sound casual.

He sees right through me, and I can see right through him, as though we both carry the same weight in silence. We exchange a few more words, and just as he’s about to leave, he says, “Let me know if you ever need a place to stay.”

That’s when the unease hits. I’ve never felt more exposed.

He was known for drawing chalk hearts around New York City, a signature that I’d encounter over the years. We never spoke again, but there was always a quiet exchange between us, a shared feeling like we both knew how to suffer. Years later, I’d hear the news that he had taken his life.

I think about that exchange often. His offer wasn’t romantic. It was a recognition, an unspoken understanding of what it’s like to feel invisible in a world that never pauses long enough to see anyone. He saw my pain before I even knew how to identify it. I wish I had the chance to return the kindness—to ask him if he was okay, if he ever needed anything, to tell him he could stay with me.

I think about my heart tattoo on my side—the one I got when I was 23. Maybe subconsciously he knew about that tattoo. Maybe he saw in me the same longing he saw in himself. Maybe we were both trying to fill the same void, fix the parts of ourselves that always seemed broken. Maybe that’s what this is—this endless search for something real, for love, for connection… something to make our heart whole.

But like him, like me, maybe none of us ever truly find it.

I finish my 3rd old fashion and realize I’ve overstayed my welcome. The world spins around me, and for a moment, I almost feel like I could be part of it. The city, the Bowery Hotel, the noise, the people—it all feels so close, yet so far. 

Maybe that’s the thing about New York. It has this way of making you feel like you’re right on the cusp of something. But you can never quite get in.

If you’re struggling with your mental health below are some resources. 

• National Suicide Prevention Lifeline (USA): Call or text 988 for immediate support.

• The Trevor Project (for LGBTQ+ individuals): Call 1-866-488-7386 or text START to 678678.

• National Alliance on Mental Illness (NAMI): Call 1-800-950-6264 for free, confidential support.