How to Go on a First Date That Doesn’t Suck

Ryan Yates
Jan 18, 2021
COMMENT

We’re revisiting this classic Autostraddle piece on queer dating as we get back to dating basics in partnership with HER’s Queer Dating 101, a series of live edutainment events that brings in concrete how-tos, insights, experts and some of your favorite Autostraddle personalities to help you find love (or whatever you’re looking for) in the time of corona. Check out the event on Nailing the First Date, complete with a live first date followed by a loving critique, on 1/19 at 6pm PT | 9pm ET!


It’s easy to have a lot of mixed expectations, feelings, nerves, hopes, excitement, boredom, dread and dreams around first dates. Sometimes all at once! Here’s how to have a good first date.


1. Lower your expectations.

Be honest with yourself about what a first date actually is: a way to spend about 45 minutes to three hours with a stranger to determine whether you have enough in common to see each other again in a context that might eventually have sexual or/and romantic vibes. That’s all! It’s easy to put a lot of pressure on yourself or on the situation: What if you forget how to talk to strangers? What if she sucks? What if she thinks you suck? What if this is the only date you’ll have all year? What if when you have a relationship you look back on this evening and it’s weird? What if they’re “the one” (“the one” is a myth) and you mess it up by talking too much about your cat? What if what if what if? — but take a deep breath and let all that stuff go.

2. Save talking for the date.

If you’re looking for someone you can hang out with in real life, focus your initial energy on hanging out in real life. On a dating app, this means keeping the conversation brief and centred around when and where you’re going to meet, and then meeting — not making days of small talk and not sexting endlessly into that great night, unless those are the main things you’re interested in. It’s okay if those are the main things you’re interested in, but if you want to date in person, you need to meet in person. Making a plan quickly, saying something like “I don’t like to text a lot before meeting someone, but I’m so excited to meet you,” and restraining yourself from doing a lot of early back-and-forth or internet stalking can all keep your expectations realistic and make the actual date itself go more smoothly.

3. Pick the right location.

So you want to meet in real life… but where do you meet in real life? The best first dates have:

  1. One-on-one interaction somewhere a little interesting but not too distracting, and
  2. Built-in parameters.

If the point of a first date is just to get enough of a sense of each other to see whether you want to see each other again, pick somewhere you can get a chance to do that one on one. Movies are fun but all you learn about a person in a movie is whether or not they can sit still and not look at their phone for a few hours, you know? And only fuckbois invite their tinder first dates to bars with all their friends. Keep it simple, keep it one-on-one, and don’t pick an activity that you’ll want to focus on more than each other (unless all you want is a friend to do that thing with, in which case it’s not really a date is it?).

Going for coffee or a drink or ice cream or juice or whatever is a default for a reason: if the date goes well, you can easily order another round, and if it doesn’t go well, finishing the first can be a natural conclusion for your time together. There are other people around, there’s probably a bathroom, and you have an easy possible opening for conversation (“What are you getting?”) if you’re stuck. If it’s really bad you can be out of there in 20 minutes, and if it’s really good you can linger for hours.

Maybe she’s not a stranger, though. Maybe you’ve been running into each other for months and you finally asked her out and she said yes. Maybe they’ve been your friend for years and you matched on tinder last night and decided to go for it. Maybe there’s some other reason you want to get big and sweeping and romantic. I totally get that! But remember how you’re keeping your expectations low? Don’t put a lot of pressure on the situation, even and maybe especially if for some reason it already feels like there’s a lot of pressure on the situation. Keep it light, keep it simple. If you really like each other you’ll have so much time for the big stuff, and if you don’t it’s way better to find out by being yourselves then by trying to force something that isn’t there.

4. It’s okay if the conversation is a little awkward.

The best thing is to let the conversation flow naturally. Do you come here often? Oh, what’s your favorite [type of establishment you’re in] in [place you live]? How long have you lived here? Why’d you move here? What was that like? But it’s okay if the conversation doesn’t flow naturally! You don’t know each other (or if you do, you don’t know each other in a dating context), you haven’t established a shared language, you don’t know where the conversational landmines are, and you might both be a little nervous. That’s okay! There will probably be awkward silences and those are okay, too. Exchange your caution for curiosity. Ask questions. Say, “tell me more,” and lean forward a little. If you don’t know what to talk about, remember you can ask about pretty much anything — you don’t know about their neighborhood, their job, their roommates, their pets, their favourite tv show as a kid, whether or not they believe in astrology, whether or not they believe in weeding their houseplants, when they got that killer haircut, what they did this weekend, or anything else. Listen to their answers. Share yours.

5. Be your real self.

Dress how you normally dress, act how you normally act and care about things you normally care about. Don’t pretend you like movies (or, say, monogamy) just because she does and she’s really pretty and you want to see her again. Don’t pretend you hate tuna tartare just because they’re vegan. Don’t pretend to love cats when you’re allergic. Don’t wear clothes that make you feel anything other than awesome. The point is to be you, not a version of yourself that you think someone else might like. And the only way for someone to like you for who you are is to be who you are just as hard as you can.

It is okay to try to be the best version of yourself — the version that’s on time when you’d sometimes be late, the version that’s not still texting that one ex, the version that did laundry a little more recently — but make sure that you’re still being yourself. Otherwise, what’s the point?

6. Follow your feelings.

It can be easy to make your takeaway from a date all about the other person — Did they like you? Does she want to see you again? — but don’t. This is as much about whether you like her as whether she likes you. Follow your feeling. Did you just feel a little bored? Did they interrupt too much? Did you hate the way she kisses? Do you just not want to see her again? Don’t see her again. Can’t stop thinking about their mouth? Can’t stop thinking about their mind? Worried it was awkward but you almost don’t care ‘cause you were so intrigued? Say you had a good time and want to see her again and see what happens.

Don’t think of a good first date as one that leads to a second. Think of a good first date as one where you got to be yourself, clear and honest and true, and got to meet someone new and see where you might line up or not.


Lesbian Sex 101 is Autostraddle’s series on how to have lesbian sex for queer women and anyone who finds this information applicable to their bodies or sexual activities.

Sex ed almost never includes queer women or our experiences, so we’re exploring pleasure, safety, relationships and more to make that information more accessible. A lot of the language in these posts is intended to make them easy to find on search engines.

Some of the body parts we talk about will be yours or your partners’ and some won’t. Some of the pronouns will be yours or your partners’ and some won’t. Some of the sexualities will be yours or your partners’ and some won’t. Some of the language will be yours or your partners’ and some won’t. Take what you want and what applies to you or what you can make apply to you and your partners and your experiences, and leave the rest!


Want to learn more? Register for Nailing the First Date on 1/19/2021 at 6pm PT | 9pm ET!