Love And Hope And Sex And Dreams

Now that we’ve finally strung together a week or so of genuinely pleasant temperatures, many of you are probably thinking about going outside. Invariably, that means a lot of you are also looking at our online dating profiles with new fervor; spring fever, at least in my experience, is a real thing, and I’m sure plenty of you are all horned up as we speak. Although I really, genuinely think you should delete your Tinder profile for the summer and see what happens, I’m old enough to know that no matter how good an idea is, people do whatever they want anyway. In that spirit, now seemed like the time to set some extremely simple ground rules for good first date behavior.

I can’t improve your personality or help you be better at talking to strangers, but after the better part of a decade dating in New York and zillions of Internet-based first dates, I’ve found some variables in date procedure that can easily be eliminated. If the stuff below goes by the book, it’s that much easier to worry about whether or not you actually like the person sitting in front of you.

Just pick the fucking location.
Dudes, huddle up: this is the subtlest and easiest of flexes, and it’s always something I notice and appreciate. By the time I agree to go on a date, we’ve almost always gone back and forth a bit on where we work, where we live, and one or two food and drink opinions. You’ve got all the info you need to look confident in your taste level, logistical capabilities and knowledge of fun places, and you should seize the opportunity to look like a functional adult. When all “planning a date” requires is considering a handful of data points and making a decision that doesn’t wildly inconvenience your date, weaseling out of the duty just makes you look kind of fussy and nervous.

This is another guy thing: gender roles are fucked up, but as they stand, women will feel like you’re not really interested if they have to chase you down to make sure you guys are still going to hang out. If you made the date several days in advance, text the afternoon before to firm up place and time. If you made it only a day or two before, text the morning of. This isn’t rocket science, it’s common courtesy.

Be on time and wait outside.
This goes for everyone involved in a date. Any decent bar in the city is going to be slammed after work almost any day of the week when it’s warm out, and no one wants to push their way through a crowd in search of a quasi-familiar face that may or have not have even shown up yet. Lean against a parking sign and play it cool until your date arrives. If you feel like you need to go inside to snag the last table, text the other person and tell them where to find you. Small, considerate gestures add up. (Actually, that last sentence could be this entire column, but I don’t think I’d get paid if that’s all I submitted.)

Ask questions.
The most awkward dates I’ve ever been on were situations where I asked the appropriate questions of the man I was with, and when he was done answering them, he just sat there and looked at me blankly instead of reciprocating. The best ones, on the other hand, were situations in which we were both genuinely curious about each other. Be curious, and be aware if you’re the one doing all the talking.

Paying is tricky and situational for everyone.
Personally, if a man wants to go on a second date with me, paying is a good move. Not because I’m hurting for the $30 of happy hour drinks or because I believe men should pay, but because paying is like picking the location: it makes a man look cool and confident and interested, and that’s the most attractive combination of characteristics a man can have on a date. On the other hand, though, I have female friends who sincerely want to split the first date check no matter what. My advice for men would be to offer once, and if your date politely offers to split, say that you’ve had a great time and you wouldn’t mind letting her get the first round next time. If she still offers, split the check–no need to belabor the point or make her feel uncomfortable. On the other hand, if the date was unexceptional, an offer to split from either party is fine.

Don’t fuck, or, I don’t know, maybe do?
I’ve had plenty of first date sex in my life but I rarely have it any more. For me, the anticipation of getting to fuck someone I really vibe with helps carry the momentum of the first date into the second one, and momentum is so precarious in the very early days of a new situation. If that’s not the case for you, then do what you want, but it’s a dynamic worth considering. Either way, definitely make out on the sidewalk like teenagers until the Uber arrives.

If you want to see her again, text the next day at the latest.
Can you believe there used to be some kind of bullshit three-day contact rule after first dates? It seems like a thing that could never have possibly been serious, but if it was, it’s definitely long gone. And again, I know gender roles are dumb and bad, but you can’t slay that dragon by yourself on a date-by-date basis, so bite the bullet for the sake of your potential relationship. You don’t have to make plans for a second date immediately, but thanking your date for her company the day after is another thing that can help sustain between-date momentum. If you had a really great time, text her when you get home that night to make sure she got home safe. I know dozens, maybe hundreds, of single women in Brooklyn, and not a one of them would find that too forward after a good date.

Be realistic about how things went.
We’ve all interacted with potential romantic partners before. We know what it looks like when things go well or when things go poorly. We know the difference. Don’t kid yourself into thinking things were great just because you were really hoping they’d be great. Ride off into the sunset with your dignity intact and spare your date the duty of rejecting you explicitly. Take the L. Love yourself.


  1. Basic politeness are what most people – men and women – arrive at with a little bit of thinking and maturity, but yes, I agree: some of us would certainly benefit from first date advice. However:
    “Can you believe there used to be some kind of bullshit three-day contact rule after first dates?” Well, reading the above make me surprised that this rule is actually considered archaic. The writer claims to “know gender roles are dumb and bad” but man, that’s one entire column dedicated to how to reinforce them.

    Emotional intelligence, anyone..?

    • Like clockwork: men get the most upset about gender roles when the ones that require them to show an ounce of consideration and care for the women in their lives are mentioned.

      Personally, I’m not interested in walking back the social expectations on men and dating until we get to walk back the ones on women, too, and that’s entirely out of my hands.

      • Like clockwork? I don’t mean to be obnoxious but it sounds to me like you may have a type. Unless you assume (incorrectly) that I am a man and meant that to indicate that my reply arrived like clockwork? Whatever the case may be: this guide reads as pretty rigid and judgemental to me (and tad bit bitter too, based on your reply.)
        A final thought: isn’t it in all of our hands to make and be the changes we want to see?

  2. ”Gender roles are fucked up”… then why should ”the guy” pay? Why is this article only written for heterosexuals? Why are women, according to the author, incapable of picking a location or confirming things?

    • It’s advice for the world we actually inhabit, not the one we’d all prefer. Nothing in my time dating in New York has indicated to me that idealism will get any of us very far, and it’s way more practical to understand the expectations our partners have been socialized to have and step up when it’s appropriate to do so and we feel comfortable doing it. If you’d like a different set of expectations for your actions, my advice would be to be very clear with potential partners before the first date. If you’re not, don’t fool yourself.

  3. Confirm? All it does is give your potential date the chance to cancel if something or someone better comes along. If I say I’ll be there, I will unless I can’t and then I’ll politely explain what happened. Confirming means you’re really having to ask your date twice to go out with you. If she thinks you’re going to flake on her, she doesn’t really want to go out with you unless she has nothing better to do.

  4. Apparently dating in Brooklyn is only for straight women who know that gender roles are fucked up but still supports them (but it’s ok because she knows it’s fucked up and so that makes it ok to embrace them sometimes isn’t that cute).

  5. You said: I had sex many times on the first date….., and you think you can give advices about dating? What kind of nonsense is that. It really looks like you are a serial dater and you meet with guys for free drinks and food instead of really looking for that special one. Giving advices about the first date is the last thing you should do based on what you said about yourself.


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