first person

All the Possible Futures

My dating profile recovered the person I used to be. My daughter forced me to confront who I wanted to become.

Photo-Illustration: Sunny Wu
Photo-Illustration: Sunny Wu

My first date was with a coffee roaster. This was a year after I left my marriage. He was a few years younger than I was and maybe an inch taller: bearded for a long time, sober for a short time, earnest in his cowboy boots. Somehow the four years between our ages widened from a data point into a mild-mannered chasm when we sat across from each other in a diner booth, drinking black coffee from heavy mugs that felt good to hold in my numb hands. In those days, I was directing approximately 20 percent of my mental and emotional energy into keeping my daughter’s hands in mittens, but my own were usually cold.

At 32, the coffee roaster was not just unmarried and childless but seemed almost awestruck by the fact of my child — as if I were a kind of celebrity for having a kid, rather than just someone who’d gotten divorced a decade earlier than most of her friends. Sitting in a diner booth, asking him what he’d been like in junior high, or grad school, or early sobriety — I sensed the messy trajectory of my own adulthood lurking behind our small talk, every clever comment or eager question buckling under its weight. It was like I’d mistakenly opened on the wrong page in a novel of manners and was now reading the chapter about courtship when I’d already read it years ago (several times, in fact.) And yet here I was.

It had been a year since I’d moved out with my daughter, who was barely 2, and in that year I mostly had been living on what I called Planet Women: surrounded by friends, leaning heavily on my mother. I was on the verge of signing papers that would finalize my divorce. It was deep winter: short days, bone-chilling cold, everyone and their runny noses clumped together on the subway. It had been a long time since anybody but my daughter had seen me in underwear.

For the first year of my separation, I’d resisted dating for a few reasons: I was exhausted, for starters — by daily caregiving, getting divorced, and mourning my marriage, in addition to my actual work as a writer and a teacher — and I wanted to prove to myself that I didn’t need anyone, at least not any man. I also worried that perhaps I was bound to keep repeating the same mistakes, so why repeat them so quickly?

Even more than I’d resisted dating, I’d resisted the apps. For all the usual reasons — the churn and scale, the bad dates, the men who were emotionally evasive and unavailable — and then some: I was afraid that only men far older than me would actually think I was young enough for them; afraid of being thrust into claustrophobic, gendered scripts where I wanted more commitment than a man I didn’t even like that much wanted from me, that we’d get stuck in the ruts of those advice-column gender archetypes. I was afraid that even having these problems (But it’s been a day and he hasn’t texted back??) would be an embarrassment at my life stage, a kind of failure. A regression.

Which is all to say: I was afraid of rejection, and I was afraid of getting addicted to crumbs of affirmation. I was a sober alcoholic who hadn’t had a drink in a decade, but from the way I chased “likes” on a tweet, it was clear that the old self was still there, thirstier than ever. I was afraid that giving her an app would be like giving her a glass of wine: She’d just want more, and more, and more. The apps felt like an explicit confession of intentionality and desire: I want this, I’m seeking this. And that intentionality made me uncomfortable. I preferred the version of things in which the universe just ambushed me with a meet-cute in a coffee shop and I didn’t have to claim responsibility for all my wanting.

Underneath this, there was an even deeper self-suspicion: What did I even deserve? After leaving my marriage, I sometimes felt that I’d had my chance and used it up. Dating again felt like claiming more than my fair share.

I’d fought hard for the tranquil sweetness of the life I’d built with my daughter since my separation, which wasn’t paradise (it was, unsurprisingly, quite tiring) but had a dyadic sturdiness that I felt safe inside of. I didn’t want to disrupt its rhythms: slipping into sweatpants once I got home from work, bundling my daughter like a plush caterpillar in her sleeping sack. It felt almost like a betrayal to want something more, as if I were admitting that somehow this wasn’t enough.

But I did want something more. I wasn’t lonely so much as I was curious, not just about the men who were out there but the possible dynamics we could have, the versions of myself I might become. I’d gotten married quickly, at 30, soon after my ex and I met, and I wanted to meet another version of myself besides the version I’d become in that marriage. It wasn’t really affirmation I was looking for, I think — it was a sense that the world could still surprise me. That I had no idea what would happen next.

My friends said, “Just put up a profile.” And, gently, they reminded me that the outside world wasn’t as all-or-nothing as the inside of my mind. I could go on a few dates, see how they went. Putting together my profile, I was fine with the text stuff. I was a creature of text, after all! (Let’s make sure we’re on the same page about: Epic Road Trips. Infinite Jest. Lunch Dessert. And by “on the same page,” I meant, You need to love all of them.) Photos were harder. Either I looked ugly or else it looked like I wanted everyone to think I was hot. (“But you do want them to think you’re hot,” my friend said, which was a fair point and sort of got to the heart of the matter. It felt unthinkably vulnerable, almost embarrassing, to want to be wanted.) In the end, I got so much input it felt like I was working with a White House cabinet of advisers: full-body shot, for sure, but no bathing suit unless I wanted even more explicit sex messages. (It was starting to seem clear I would get plenty anyway.) I shouldn’t just post flattering photos, my friend said, but photos where I was doing something. This forced me to ask myself, never one with many hobbies, What did I actually do? The one of me wildly gesticulating in front of a row of bookshelves, grinning. “That’s you,” my friend said. And she was right.

Sometimes I cringed imagining the many parts of my profile that might categorically turn someone away — the fact that I was a mother, that I didn’t drink — but then I hated myself for worrying about this, as if I were disowning these parts of myself, when anyone turned away by them obviously wasn’t a good partner for me anyway. But I wanted their messages, I wanted them to want me, wanted everyone to.

Because I was afraid of getting addicted to the apps, I only registered for one. And like Odysseus asking his men to tie him to the mast of his ship as they sailed past the Sirens, I set myself some ground rules: I could only spend a half-hour on the app every other day. Well, maybe 20 minutes every day. Not in the morning (my best work time). Not at night (too close to sleep). Never around my daughter. This last one felt especially important. The idea that I’d be distant or distracted when I was with her, squinting at some dude’s rock-climbing selfie to see if he was really as tall as he claimed, instead of listening to her try to pronounce the word avocado — it was unacceptable. Plus, and this part I wasn’t as honest with myself about, the less frequently I checked the more would be waiting for me there. It was like that famous experiment where the kid who waits longer gets double the marshmallows.

Before too long, however, I was breaking all my rules, eating marshmallows straight from the bag. I would let go of my half-hour rule and my not-before-sleep rule and I’d just lie in bed scrolling through possible faces, possible futures.

I liked to tell myself I was open-minded. My main nonnegotiable was height, but I was surprised by how many of these men were six feet tall, or more! I asked my friend, “Have men gotten taller?” She looked at me like the idiot that I was, almost squinting in disbelief. “They haven’t gotten taller. They just lie.”

From all these improbably tall possibilities — the finance guys and “user experience” specialists, the Jersey songwriter who loved ugly Christmas sweaters, the Rikers Island CO, the banker who bragged about his roof deck and started texting every single morning to ask “How are you?” — I decided on the coffee roaster as the first man I would meet for an actual date. He looked handsome. He seemed kind and playful. No bullshit but witty. Over the app, we traded fake mocktail names inspired by Infinite Jest; which made me feel faintly nostalgic, almost like I was going on a date with a prior version of myself: a 20-something grad student who prioritized deep talks and intellectual communion above all else.

The diner where we met was called Little Purity, which seemed like about as much purity as I had left. It’s not that I felt stained by my past, exactly, but I felt barnacled with experience and history and breakups and guilt and memories of my divorce lawyer’s office, with all the ways I’d let myself and others down.

Near the beginning of our date, I asked the roaster if he hated the coffee we were drinking — this seemed like an abiding peril in the world that knowing too much about anything made you less able to take pleasure in it. He said he was enjoying it, and it looked like he meant it, and I felt a great surge of tenderness for him, for the spirit of kindness and goodwill he seemed to bring to his dealings with the world and, weirdly, a sense of fierce gratitude for this goodness in him that felt so palpable, like I could trust him with my life, if it came to that. But why would it? I wasn’t even sure I would go out with him again.

I liked his mind, his easy sense of humor, his soft-spoken masculinity, and absolutely my 28-year-old self would have gone out with him in a heartbeat, or my 22-year-old self, or really any prior version of myself, before this one, who lived in a world of baby wipes and food pouches and changing-table shticks — what would me and the toddler riff about this time?

It wasn’t that I couldn’t imagine this bearded saint who I barely knew welcoming my child into his life but that I already somehow felt like his mother. I felt unglued from our first-date script. Like he was my student, or my bartender, or my son. A few times during the date, I was ambushed by sudden strange imaginings of impossible displays of closeness, like leaning my head against his chest, right there in the diner, in the middle of the afternoon, and smelling the earthy scent of ancient roasters, listening to the slow, blue-whale steady beating of his heart. It was as if the only modes my psyche knew were either to take care of someone or to beg him to take care of me.

At the end of our date, we hugged on the sidewalk. When he texted later that night, I said he was lovely but I didn’t think we should go out again.

I kept trying. Soon, in fact, I found myself dating two men at once. This wasn’t something I’d ever done before in my long career as a serial monogamist — devoted to consuming love affairs that left little room for anyone, really anything, else. There was a younger man who loved literature and Sweetgreen salads and SoulCycle workouts and honestly just the sheer fact of being alive. From the very first moment I sat down beside him, eating olives in a little Italian restaurant on a cold night, the energy between us felt fluid and forceful. It seemed to exist apart from us, as if it had preceded us. He was ridiculously good looking and knew it, with a smile so large it narrowed his gaze to a squint, but the knowledge of his attractiveness hadn’t soured him. He brought it with him everywhere, like a slim leather wallet. On our first date, he held my hand across the table, in the shadow of our towering focaccia, and cupped his palm around my waist when I got up from my chair. It was thrilling to be around someone with so much confidence, so much ease in the world. Someone so unbroken.

“Were you popular in junior high school?” I asked him. (I liked asking this question.) Yes, he confessed. And so I asked a follow-up question. (I liked asking follow-up questions.) What was it like, being popular? The question was like asking to see someone’s photographs from an exotic vacation. Speaking of which: He sent me more selfies than anyone else I’d ever met. My phone started running out of storage. He sent me a selfie that just showed his paper bag from Sweetgreen and his loafers on the midtown sidewalk. “I should be shot,” he texted.

Perhaps, I thought. But not yet. 

Then there was the second man, a few years older than me, who was also divorced but had no children. He’d gotten a Ph.D. in philosophy, but now he worked at a hedge fund. He made more sense, but he also made me anxious. I never quite felt like enough for him. I could imagine our lives coming together, our shared bank accounts and Park Slope brownstone, but I did not feel, with him, that same sense of giddy infinitude.

Dating these two men at once — one who felt pointed toward a past version of myself, the other toward my future — crystallized something about the fertile purgatory of that moment in my life, when I was 36 years old, stranded between youth and middle age: I felt so young on early dates, in those moments of wondering whether someone would kiss me on the sidewalk and what it would feel like. But I also felt my age: the essential difference between what I’d done with men before and what I was doing now. The difference was my divorce, the life I’d tried to build, and the difference was my daughter, the life I needed to build with her.

It was daunting to imagine dating in the high-stakes landscape of this single-mother life, as if dating someone was implicitly asking for their total immersion into this land of diapers, tantrums, bath time, nightmare crying. I’d always escalated quickly in relationships, and now it seemed like I’d created another trap for doing just that.

Dating two men at once was meant to be a way of keeping myself from getting too serious too quickly; another version of Odysseus tying himself to the mast, this time so I couldn’t hear the siren song of premature commitment. It was a therapist-supported venture. She and I had spent years discussing my relationship to escalation, how it was one way of evading uncertainty. Making something serious was one way of convincing myself I’d never lose it. But this was part of dating I was coming to understand: the tenderness of tentatively letting yourself want things — particular people and the lives they represented — while knowing you might not get to have them, or you’d only have them for a little while and that really having wasn’t the right language. It wasn’t something you got to possess, this kind of connection. You just got to show up for it.

Like the drizzly Sunday afternoon when I ate shakshuka with the SoulCycler and drank too much coffee and raced back from the bathroom to keep talking to him because there was so much to say and we’d never say it all. Some part of me hadn’t fully believed it would ever feel that way again with anyone. When I brought him back to my apartment, the air was bruised and misting with rain and I let him take off my clothes as the light faded beyond my windows. Then he went back to Manhattan to watch the Super Bowl with his friends while I took a bath and watched cell-phone videos of my daughter taking baths. There are no do-overs in this life. But sometimes you meet someone who lets you believe there could be.

When I told my mother I was seeing two different men, she said, “Well, eventually it’ll be one. Or zero.” Then she asked how nap time had been going. My daughter would always be more interesting to her than any man.

I kept telling myself I should end it with one of them. Next week always seemed like a good time for that.

Before I could end anything, the whole world ended instead. The pandemic hit. My university closed. The grocery stores ran out of cleaning supplies and baby Tylenol. When the world brought me back to my daughter — just the two of us, stuck in that apartment with no company besides my COVID — it almost felt like I was being punished for wanting more. This is your life, the world said. Don’t pretend; don’t forget.  

This quarantine was a reminder that my life was textured, more than anything, by daily rhythms of responsibility. “Let’s make sure we’re on the same page about epic road trips,” I’d written on my profile, but in truth, I was looking for someone to share a life composed of domestic moments more than spontaneous travel; someone who could help make sure there were five different flavors of ice cream in the freezer and Band-Aids in the medicine cabinets.

With the SoulCycler, I’d felt like I was in my 20s again, back when I believed that what mattered most in partnership was whether you never ran out of things to talk about. I used to think of this as the white-room test: Trapped in an empty room, with bare walls and nothing to do, how long would you remain fascinated by someone? This hadn’t even been a foolproof relationship rubric back in my 20s, but it seemed even less relevant now. Life wasn’t a white room. It was full of logistical frustrations, domestic chores, child-care tallies, sick days and snow days and work deadlines and, if you got lucky, years spent in the company of someone whose anecdotes you were still charmed by, even if you’d heard them many times already. What I needed now was someone with whom I could live in all the other rooms: putting away groceries in the kitchen, chatting about our days while we clipped our toenails in the bathroom, figuring out how to get the kid back to sleep in her nursery  —someone with whom dailiness could feel not like the enemy of wonder but its conduit.

If I’d worried, in the beginning, that dating again was a betrayal of the cozy domestic life I’d built with my daughter — an attempt to flee it for a prior version of myself — during quarantine I started to come around to the opposite idea: that perhaps romance didn’t represent my urge to run away from daily life but simply my desire to share it with someone else, to disrupt the story I’d told myself that the end of my marriage was a sign that I’d failed at domesticity or that some part of me didn’t want domesticity. Maybe I was just hunting for a version of domesticity in which I could be happy.

I didn’t know everything about who I was, and what I wanted — if anything, I’d learn how to not know these things about myself more gracefully. But I knew I wanted to lie in bed, in the dark, talking about our days: Venting about petty squabbles at work. Laughing so hard our sides hurt. Poring over my daughter’s latest shenanigans. Curling up in bed, even with pinkeye and a hacking cough. This wasn’t so much, was it? It was just a life. It was everything.

All the Possible Futures