A Guide To First Date Behavior (For Everyone)


I was reading a recent Brooklyn Magazine article called Love And Hope And Sex And Dreams: A Guide To First Date Behavior which contains some great tips and advice targeted toward straight men who might want to impress the women they’re on a date with. There isn’t anything wrong with writing advice geared toward men or anything, but I figured that everybody would benefit from a guide to first date behavior, not just straight men, so here we are. A Guide to First Date Behavior, for everyone, regardless of what gender you are or who you date.

Decide who is going to plan the date, then plan

Straight men, let’s be realistic and just assume that nine times out of ten, the straight woman you want to take on a first date is going to expect you to plan the date. Nothing wrong with that, and if you feel like adhering to that general dating norm, go for it. The advantage of planning a first date in its entirety is that search engines and crowd-sourced review sites have made figuring out an appropriate date venue based on price and dress code extremely easy. What I’m saying is if you’re a straight guy who is expected to both plan the date and pay for the date, it behooves you to pick where is exactly you plan to spend money because it allows you to pick a place based on how much you can expect to spend. Let’s say you don’t like traditional dating norms, or you’re just not a straight man, who picks the location then? Well, there’s a few ways to approach it. First, you can always make it collaborative, with one of you picking part of the date, and the other picking another part. If you’re doing a bar then a place to grab a light bite after, alternate who picks with. Make it a conversation and not a one-person group project. Or, whoever you are regardless of sexual orientation or gender, volunteer to plan the date. It’s as simple as saying “I’d love to plan this date” and move forward from there. Whoever  plans the date should be sure that the plans are as specific as possible, even if they are just meeting at a specific time and place and then winging it. I’ve had dates where I just walked around an area and then popped into whatever bar caught our eyes, but I first needed to give a time and place to meet. When planning, do so with enthusiasm and clarity. If you can’t do that, regardless of gender or sexual orientation, maybe go for a more collaborative role. It’s hard planning a date when you’re new in town, or are new to dating in general, so don’t be afraid to say that and ask for input.


I’m stealing this one directly from that article, but think that confirming the date really can and should be done by whomever decides to do it first. If  you’re planning a date, your clarity will assuage any fears about you being flaky. That said, it’s always good to confirm a date either the day before, or the day of. Either person who is actually going on the date can do it, but if you haven’t received a confirmation at least 8 hours before the date, reach out and get confirmation. No long message needed, and you don’t need to actually use the words “Confirm” or “Confirmation” when you reach out. My go to is basically “Hey, really looking forward to seeing/meeting you tonight/tomorrow. Let me know if anything comes up, or if you’re running late. No worries”. You can be as loose as that, or as rigid as sending a formal request for a confirmation listing time, place, blood type, whatever the hell else is relevant for your date.

Be on time and wait outside. Or not. Give a heads up if you’re running late.

Being on time is great advice, and waiting outside for your date is great too, especially if they’ve never met you. A great reason to not wait outside is if the place you’re going to is going to fill up quickly or is already pretty packed. In that case, try to stake out a table and reach out to your date when you get one. Meeting someone in a crowded bar can be awkward, but meeting someone at a crowded bar where there is only standing room is even more awkward. That said, shit happens. Train delays happen. Traffic happens. Being held up by a chatty coworker happens. Everyone at some point in their life will be late for something. Dates are awkward enough without having to worry about whether or not you’re being stood up. If you’re running late, or even if you think you might be running late, give your date a heads up with how long you expect to be delayed. If you’re wondering how long you might be delayed, use a search engine to figure out the estimated time between your current location and destination and specifically tell your date “This search engine says I should be there by X minutes. Sorry for the delay”. If you’re unable to reach out when you realize you’ll be running late, apologize if you are late and buy the first round.

Engage and Actively Listen

When you’re talking to a date, there are really only two things you should be doing. Either you’re engaging with them by asking them questions, or you’re actively listening to them. Ask questions that you can’t answer in one word, listen to their responses and build on each response. When you’re listening, pay attention to their body language when talking about a subject. You might want to bring up sex, or past relationships, religion, politics, or other conversation topics people usually avoid, and whether or not you can or should you can read through your dates face and body language. If they’re grimacing when they talk about an Ex, maybe drop the subject and save it for a later date. If they look more receptive and engaged when you talk about a different topic, try to dig deeper into that. Keep building on the conversations that seem to be things they want to talk about, and you’ll establish a much better rapport.

Decide who is going to pay for the date, then pay

Look, we know what the general expectations are when it comes to a straight date, so let’s get that out of the way. Men, more often than not you’ll be expected to pay for a first date. This isn’t always the case, and if you feel like you shouldn’t pay for a first date, that’s fine, just bear in mind that depending on the woman you’re on a date with, this can either help or harm your chances for a second date. Personally, I usually pay for first dates but if I go on a first date and it sucks and I have no intention of ever seeing her again, and she offers to pay  will take her up on that offer. I hold no pretense that I’m either a gentleman or chivalric because quite honestly, I’d rather have an extra $50 in my pocket than to pay for some random person’s drinks who I never want to see again. Whether or not you choose to pay for the whole date, half of the date, or none of the date is up to you, but you need to remember that society, by and large, has a very heteronormative way of looking at mating and dating. If you decide before the date even begins that you want to split the check or have her pay entirely, discuss it before the date. You, as a straight guy, might be thinking that doing that would almost certainly guarantee that you wont go on first dates ever again. That isn’t exactly true, but you will turn-off a lot of women if that’s your preference and to that I say….so? Your preferences, whether financial or otherwise, may lose you some opportunities but hey, at least you’ve got all the money you would have spent on your date, rather than half of it. If you aren’t strictly a straight man and want to know how to handle paying for dates, here’s a general guideline. Whoever says that they will pay for the date, pays for the date. Not whoever asks for the date, but whoever says they will pay for the date. What if no one specifically says they will pay for the date? Then come to a consensus either prior to the date, which is advised, or during the date.I’d recommend for the folks who aren’t always expected to pay on the first date that they start the conversation. There are ways of talking about paying for dates without using the words “money” or “pay” and that’s the way to go. If you’ve got two things planned for the date, like say drinks and a show, you can start the who pays conversation, if you want to split, by asking if they want to get drinks and you’ll get tickets to the show, or vice versa. If you want to pay for a date and volunteer, you can say “Let me take you out” and let that be the end of it. If you want them to pay, sorry, but I can’t think of a more subtle way then just saying “Can you get this date?”. That maybe wont work for a first date, but if you’ve been on 1 or 2 dates that you’ve paid for, you’re well within your rights to say “Can you get this?”. Regardless of who says they are going to pay, always bring enough money with you to pay for the date in full if need be. Worst case scenario, they bail on you during the date and you’re on the hook for the whole cost and I’m pretty sure the venue isn’t going to accept “your half” of the cost of your date.

Sex or No Sex is up to you, just be wary of how First Date Sex is viewed

I’m all for people making responsible decisions with their sexuality if they’re an adult. I also know that sex on the first date is generally viewed as a negative by society at large. Let me be explicit here, if you have sex on the first date and you’re a straight women, a lot of people will either have a problem with that or think that it signifies your inadequacy as “girlfriend material”. I don’t think that’s fair, but I do know that most people see first date sex that way. So, if you are a straight woman, Caveat Dator, as they say. Anyway, first date sex is generally viewed as a negative for most people, but not all, and it’s a crap shoot. Do it if you want, but know that it’s a risky move. I’m not against first date sex, but I am pro-knowing someone before I sleep with them IF I’m looking for something serious. If you’re dating just to date, and an opportunity arises, protect yourself and be safe. If you’re dating looking for the one, maybe skip the first date sex. Or not. Entirely up to you.

If you want to see them again, say so

The three-day rule is a rule of the bygone era. Drop it. Instead of waiting three days, text the next day to start working on date planning. You don’t have to dive right into planning the date immediately, but be sure that after your date you’re clear that your interest extends to more than just the first date. I usually do a text the night of the date if it’s before midnight by the time I get home from the date, or the next day. The next day is a great timeframe to reach out if you want to see them again, and even the day after is okay, if a little late, but don’t wait three days. Not because waiting three days is inherently bad, but people are just going to assume that you’re doing the three-day rule thing.

Recognize rejection

Some people are clear about their desire to see you for a second date, while others take a more passive approach to rejection after a date. You already know what “thanks, not interested” looks like so we’ll skip all the variations on it. Instead, here are some examples that while your date might not have been terrible, they just don’t want to see you again. These include: Responding to your text days later. Not responding to your text at all. Being tentative about their availability to the point of absurdity. Telling you they’re “really busy” without giving you a timeframe for when they wont be busy. Any variation of “I like you, but…” that leaves the door open for seeing each other again, but not in a romantic way.They close the date by saying “it was nice meeting you” instead of “great meeting you, let’s do this again” or something similar. A good unwritten rule is if you think you’re being rejected, you’re probably being rejected. It occasionally gets a bit difficult to interpret passive rejection, so don’t be afraid to ask them directly if they want a second date.

Above all else, have fun and be safe. Always meet in a public place on a first date, use protection if you decide sex is in the cards, and if you get rejected handle it gracefully. I think that’s pretty good dating advice that we can all use, regardless of gender or sexual orientation. 😊

Good Luck Out There.

2 thoughts on “A Guide To First Date Behavior (For Everyone)

  1. Good stuff! A lot of this seems to be common sense but…as we all know, it doesn’t always work out that way. I always offer to pay or give money towards SOMETHING as early as Date 1, but once we reach 2 or 3 I will INSIST on paying for something — whether it’s the dinner part or the drinks part or, at the very least, one drink. As for after the date, it should be fairly obvious if you both want to see each other again and in the same token, fairly obvious if you don’t. Yet I’ve had dates that have gone awry or had ZERO chemistry (with an awkward/cold goodbye) and still got asked out a second time. WHEN DID DATING BECOME SO FRICKIN DIFFICULT?

    Liked by 1 person

    • I think the idea that a lack of interest is obvious sounds good in theory, but in practice that’s not always the case. Straight men are very often told, whether directly or indirectly, to ignore signs that a woman is disinterested because persistence will win her over. There are also some men and women who are just plain oblivious. I think that some people can spot signs of disinterest very easily, but a lot of people can’t, or just refuse to acknowledge them.


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