How to Have a Good First Date

I have been on 76 first dates in the past three and a half years since moving from a small town to New York City. I know this because (like many before me) I have been keeping a spreadsheet. 

Dating had always felt like an experience I’d missed out on during the two relationships I’d been in for most of my 20s. But once I was actually doing it, I felt overwhelmed by the sheer number of prospects. I needed a way to keep track of them all—and I wanted to be able to observe patterns from my experiences.

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The reality is, a lot of first dates do not turn into second dates. You have the same conversations over and over, go on mediocre date after mediocre date. It can feel like a chore. Dating in New York necessitates efficiency, but it can be hard to make quick decisions. If someone’s dating app profile seems only okay, should I still give them a chance? Can a mediocre first date turn into a great second date? What if I’ve already met the right person but discounted them too quickly?

I wanted to use data to make the process more efficient—to figure out what made a first date good. And I’ve found that instead of approaching every first date as the search for a partner, it’s important to be open to whatever unfolds, and to embrace the unexpected adventures that appear along the way.

My spreadsheet columns are simple: basic biographical information, first date activity, and general notes. Other friends have told me about more elaborate categories: Early on in my spreadsheet, I had a conversation with a friend at a dinner party who was so moved by an 1896 painting of three Dutch girls peeling potatoes at the Met that he would surreptitiously lead each date to the gallery and note their reaction. (He has since moved to California to be with a woman who he never took to see it.) 

Forty-six of my 76 first dates involved getting drinks, 13 were walks, and 11 were coffee. A little less than half of those dates (35) led to second dates. 

Less than a quarter of my first dates (15) led to four dates or more. I have gone on dates with four Matts, four Joshes, and four Dans. 

I met 56 men via dating apps, and the other 20 through mutual friends, dating events, and parties. Dating apps get a lot of hate, but I will say, they’ve led to better first dates.

There’s a scriptedness to dating in a big city: How many messages you send on Hinge before one person asks the other out. The standard first date activities. The typical first date questions. Who pays. How long you wait to text afterwards if you had a good time. When it’s acceptable to mutually ghost if you didn’t. 

It’s a dance that nobody choreographed, but with distinct steps we’re supposed to pick up as we go. I can tell if somebody is an experienced dater by where they sit in a bar (next to somebody allows for casual physical contact, across from them doesn’t) or the kinds of questions they ask (“so how’s your New York dating experience been?” to suss out where I am emotionally.)

My spreadsheet chronicles 40 months of rom-com worthy exploits: I’ve (accidentally) dated multiple people in the same community choir at the same time, then found out one of them was also dating one of my close friends. I reconnected with a college crush. I went on a date with a barista I’d long admired (who turned out to be so unpleasant I had to stop going to my favorite cafe). People I’ve dated have set me up on blind dates. I was asked out on the street by a Parisian doctor, and met somebody just before midnight at a New Year’s Eve party.

Some dates have been lackluster (next to Joe from 2023, I wrote: doesn’t believe that climate change is “that big a deal”). I’ve been ghosted, strung along, rejected. In one of the spreadsheet columns, I put an x if somebody has treated me poorly: lowercase for little things like ghosting or rudeness (14)—uppercase for worse (2). 

And yet—and I may be the only person to have ever written these words—dating in New York has been so much fun. And the key to that, for me, has been learning how to enjoy first dates.

It’s strange to meet people within such a predetermined context, as if this is their audition for a romantic position in my life, with no other options for what the relationship can become.

Often, on a first date, somebody will ask: What are you looking for? 

The problem is, if (like me), you’re “looking for” love, or a life partner, then every date where that doesn’t happen can feel like a failure. If dating is framed as the search for something missing, how do you enjoy the process of finding it? 

I like to approach first dates as an opportunity to step into somebody’s world. When else do you get to spend a few hours getting to know a stranger? I like to see how my date approaches meeting someone new, the questions they ask, the way they carry themselves. I like to see who I become in their presence.

I try to get something out of every date, even if it’s not romance. I’ve discovered my favorite neighborhood bars, learned about new sci-fi books, picked up a new favorite question to ask other people I go on dates with (what qualities do you look for in friends?), and had conversations about how trying to do something you love professionally changes your relationship to it. And I’ve made many friends (as many as 15, my spreadsheet says). 

Dating is most fun when I can hold multiple truths at once: It can be the search for a partner, and also an experience, an adventure, an opportunity to learn something new.

Dating has also made me a more confident person. It’s influenced the way I approach new experiences, and how I think about the world. I think it’s made me better equipped to find the kind of relationship I want. 

I’ve learned to evaluate people based not on the facts of their lives (like their job or hobbies) but on how I feel when I’m with them. Are they kind? Do we laugh? Do I feel like myself? 

A former circus coach of mine had a strategy for when we got stuck trying to choreograph new sequences, that I think about when the monotony of dating has taken hold. Instead of trying to create something perfect, she’d have us improvise. She’d tell us to notice the patterns we fell into, the movements we gravitated towards. She’d have us pay attention to the boredom, and then change one small thing. She’d tell us to focus on what felt good, rather than what looked good. 

Dating also needs some improv. It requires moving in directions that feel right, without trying to control what those directions are. It’s about finding ways to venture through mediocrity until you stumble on magic.