Is a first date ever fun?

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Hi Meredith,

I'm 25, almost 26, never been in a relationship. I want to be close with somebody, but I'm very anxious and tend to overthink things, and the few times that I've managed to go on dates, the whole process of negotiating the time/place/manner, of trying to be myself but not too much, of trying to be chill, leaves me so stressed and performative that even if the other person has a reasonable time, I don't enjoy it at all and can't see myself enjoying any future time spent with the person.

I mostly tell myself that for now, there's more to life than dating, that I'm not ready for it yet, that if work hard in therapy one day I'll be ready. Every few months I get back on the dating apps for a week or so to check how I feel and gauge my progress, and things do seem to be easier each time. And whenever I think I might be interested in someone I know, it's easy to convince myself they're off-limits, out of my league, not worth risking the friendship, etc. So I've mostly been holding still the past few years.

But I'm tired of feeling like I'm putting my future on hold while seeing my friends get new partners or announce engagements seemingly every month. And I also know I'm a perfectionist, and that the best way to get more comfortable with something is to just do it more, and that the best way to meet people is to put yourself out there. So I'm thinking about getting back into it for longer than a week this time. My question is: How do you relax and be "authentic" interacting with someone when there's so much potentially riding on it? How can you lower the stakes and treat dating as "practice" while still being genuinely interested in the person you're dating? Is there any such thing as a genuinely fun first date?

– Thanks, No Chill

"Is there any such thing as a genuinely fun first date?"

Sure, but maybe not for you. (Don't worry, I’m with you. I'm more of a sixth date kind of person.)

The most important thing is that yes, quantity helps. You explained it best; when you put yourself out there, "things do seem to be easier each time." The process becomes more familiar. You don't have to work as hard to feel like you have some control over the process.

You should accept, though, that when you're uncomfortable on a first date – when you're trying to be present while also finding control – well ... that is your authentic self. You're the kind of person who might need a second date with someone to figure out whether you like them. You might be the exact person who'd benefit from a Zoom first date, where you can control your own surroundings and pay attention to someone for forty-five minutes without having to think about what you're wearing, who's around, whether the other person is having a good time, etc.

I think you can do work in therapy while dating. Multi-tasking is good. But also, use your therapy time to put these dates in context. There isn't much riding on any one interaction. There's potential – maybe some hope – but it's not like you're taking a pass-fail class. A second date should be pretty low stakes too.

Also, make sure your friends know you're looking. Ask them for advice. Your community should be thinking of you.

– Meredith

Readers? What makes a first date fun? What mode do you put yourself in to enjoy it? Are all first dates performative?