What are the odds?

Newly single adventures in online dating.

A True Life Built is a living photo essay on starting over and building a truer life. It’s for anyone, at any age, who is finding the courage to begin again. Subscribe for free weekly posts.

Photo meetup, February 2022.

Last February, I did something utterly unlike me: I voluntarily signed up to mingle with strangers. Normally, that falls near the bottom of my list of fun activities, but I was craving human connection: my divorce had recently ended and my friends were hunkered down with Omicron. I wanted some variety, something to break up the monotonous slog of deep winter.

On a whim, I signed up for three events on Meetup, free gatherings organized around common interests. There are dozens each week in New York: pickleball and Harry Potter ornament making, chess and smutty book clubs, pussy plate painting and Jane Austen trivia. True to my inner introvert, I picked a photo walk, a trip to the Guggenheim, and “coffee and conversation,” a Sunday afternoon gathering in a café. This being Valentine’s season, the discussion prompt was “dating apps.” I figured I could meet both men and women—and everyone would probably be single.

I didn’t have a lot of experience on the apps, but I did have opinions. I had dabbled in online dating and had discovered the standard truths: the thrill of variety, the tedium of texting, the frustrations of ghosting. I quickly learned how to screen out anyone who set me on edge. But Bumble fed me 50 new matches a day, and even after I narrowed the pool, there were just so many options. I knew dating was a number’s game, and I wasn’t in any rush, but I felt daunted by the infinite permutations.

When you meet people through work or friends, there’s a certain level of commonality baked in. But in online dating, the only baseline is that you’re both single (probably) and both live in New York. You can have a perfectly pleasant online chat and then grab a coffee and learn that your date loves mosh pits or hates his ex or has Homer Simpson tattoos. I’d leave dates bemused by the randomness of it all. I like order and patterns; I wanted my efforts to generate a predictable result. But online dating defied predictions, the apps pinging with the clatter of a casino.

Armed with my dating opinions and bright lipstick, I slogged through the snow to a nondescript midtown café for my first meetup. It was hilariously awkward: a dozen strangers clutching coffee and trading dating stories. There was a guy who talked too much, a nervous man taking notes on a legal yellow pad, a lovely British woman with wild hair and a warm laugh, and an Indian guy who reminded me of my ex and who kept trying to catch my eye.

Then there was a guy a few seats down who—wait a minute!—looked oddly familiar. I’m terrible with faces, and it took me a while to place that we’d met online and gone on an unremarkable date the summer before. My heart raced as I racked my brain trying to remember how it ended: Did he ghost me? Did I ghost him? Oh dear, I hope not?! Also, honestly, what were the odds?

There are several million Bumble users in New York, and I had only been on a handful of first dates. There are millions more on Meetup, and this was my first event. The odds of this particular Venn diagram were—someone help me with the math here—extremely unlikely. For the first time, I regretted not taking statistics. My father had always told me it would come in handy, presumably for situations like this one.

I finally placed that it had been a mutual ghosting and breathed a sigh of relief. Both of us discussed dating apps; neither of us mentioned our date. I left the meetup with the phone number of the British woman and none of the men’s. I was relieved to leave and proud of myself for going. Against all odds, I had walked into a thoroughly awkward situation and enjoyed myself—and left with a funny story to tell.

Photo meetup, February 2022.

Two weeks after the meetup at the café, I walked into my local pharmacy to pick up a prescription, feeling like hot garbage. I was sick and grieving my divorce, in sweats and snow boots, my morning hair standing straight up like a Treasure Troll. Since I was there, I grabbed some tampons and pads—they only had a jumbo pack—and made my way to the counter to pay.

“You look familiar,” the pharmacist said, ringing me up. “Were you at a meetup recently?” I looked up over my mountain of period products and froze: It was the Indian guy who’d been trying to catch my eye. I quickly tallied the absurdity of the situation: my disheveled state, the tampons, the last name on my prescription that clearly indicated I’d been married to an Indian, my presence at the Valentine’s meetup that suggested I no longer was.

Mortified, I made a few flustered comments about the event while shoving my drugs and pads in my purse. He offered to text me when the refill came in. I declined, unclear on the protocols of flirting with one’s pharmacist, and hurried out of the store, my cheeks burning. Then I started laughing hysterically and sending breathless voice memos to my friends. Of all the pharmacies in all the world, and I had to walk into his. Seriously, what are the odds?? Absurdly improbable.

For the rest of the year my pharmacist and I chatted whenever I came into the store. I was friendly but reserved, not yet ready to entertain the idea of dating seriously. The meetups had proven that I could connect with strangers, and even enjoy the experience, no matter how awkward the encounter. But I didn’t yet trust myself with what came next, to pick someone who was safe to love.

I knew the type of man I had picked at 21, and I knew clearly what I didn’t want again. But I didn’t yet know what I did want, what type of partner that would suit me at 41. I had learned some romantic lessons the hard way and it shook my faith in my own judgement. I trusted my taste in friends—my life was filled with delightful women—but not my taste in men. My desire to control the dating odds was actually a desire for certainty: Who will love me? Who will I love?

But there was no way to know without showing up, without walking into rooms with strangers, brave and open, with little way to predict which way the encounter might lead. Which part of me would light up? Which part of them? To learn the answers, I first had to live the questions, to trust enough to let the unknown unfold as it may.

In November, nine months after my first meetup and a year after my divorce, I decided to give online dating another try. A girlfriend and I declared it Manvember and dove into the apps, swapping ridiculous profile photos of men wearing unicorn suits and posing with penguins. We hyped each other up to embrace the randomness, and I regaled her with the unlikely tale of my pharmacist.

Then, one evening, a familiar face popped up on Bumble: my pharmacist. According to his profile, he had joined Bumble the week before. I was one of his first matches. I yelped in surprise and dropped my phone. Then I immediately texted all my friends: “I JUST MATCHED WITH MY PHARMACIST DO I SWIPE RIGHT OR LEFT???”

“Which way is YES??” a friend texted back immediately.
“Is it weird that he knows your prescriptions?” another said.
“I mean, the universe is telling you to meet, you cannot deny that,” said a third.

Yes, it was weird he knew my prescriptions, and he also now knew for sure I was single. This was our third chance interaction in a year. It was no longer a Venn diagram but a fractal, apparent randomness with an underlying symmetry. A chance discussion on dating apps had arced back to the apps themselves. The odds were astronomical, irresistible. Anyway, I needed to pick up my prescription. I swiped right.

We met at a café near the pharmacy, drinking lattes from crystal whiskey tumblers and chatting easily without a counter between us. He handed me my prescription—a dating first—and told me about his life. I couldn’t stop laughing at the randomness of all, at the string of chances that brought me to this table, to talk to this man.

I had no way of knowing which way this moment might lead: I might have a fun fling or I might need a new pharmacy. Maybe that was OK. Maybe I could be brave enough to simply show up and meet people in all their unpredictable glory. Maybe I could relax and enjoy the unfolding story without knowing how it ends.

Photo meetup, February 2022.

One of the unexpected joys of starting over has been hearing from others on similar journeys. If something resonates with you, I’d love for you to leave a comment, drop me an email or share a post with a friend!

Liz is a writer and photographer based in Brooklyn.