10 Tips For A Successful First Date

In my last post, I talked about a particularly memorable first date. And in his last post, MB talked about an even more memorable one. Losing his virginity on a first date. So I thought it would be a good idea to give you some tips on how to have a successful first date.

Now, it’s important to clarify a few things first. As I mentioned in my last post, everyone has a different definition of successful. But in this case, I’m going to define successful as having a great time and giving yourself the best possible chance to have sex at the end.

1. Use pre-date texting wisely

By this point, I’m going to assume you already have a girl’s number, whether you met her on the dating apps, through friends, or through cold approach. If you’re having trouble getting a girl’s number, stay tuned for a post on that in the future, but that’s outside the scope of this post.

Once you have her number, it’s important that you’re smart about texting. I know that sounds pretty open-ended, so here are a few concrete strategies to keep in mind. First, don’t be boring. Avoid simple, dull questions like “how are you?” or “what are you doing?” at all costs. If you must ask them, also include some type of witty remark along with the question. Instead, find something about her profile (if you met on an app) and ask her a funny or flirtatious question about it. If you met in person, talk about the party where you met or something funny that happened that night. But here’s the thing – it can be hard not to be boring over text. For all that’s been written on text game, there’s only so much texting you can do before it starts to get boring. Which leads me to my next point about texting.

Make plans after exchanging just a few texts. Here’s what you have to remember. Even if you know that you’re planning to ask her out after, say 10 texts or 2 days, she doesn’t know that. She might get bored of playing the texting game and stop responding to you before you have a chance to ask her out. I’d recommend exchanging no more than 4 texts each before you ask her out.

2. Make concrete plans

When it comes to making plans, be definitive and take the lead. Don’t ask what her favorite bars are, which nights she’s free, or any other questions that put pressure on her to decide. State a plan and then let her react to it. When you ask her out, it should sound more like, “Let’s meet at Bar X on Thursday evening at 9pm” and not like, “Ok, what are your favorite bars? And what nights are you free?” If she’s not free the night you propose, or if she hates the place you suggest, she’ll let you know. And then she’ll either propose another plan or give you the chance to do that.

The only possible exception to this is if you’re in a completely new city you’ve never visited before. In that situation, I’ve asked girls to pick the place because I don’t want to accidentally pick somewhere that has an awkward vibe for a first date. But you should make it clear you’re visiting from out of town and don’t normally ask girls to pick the place.

3. Pick the right place

The most important element of this is picking a place that’s not too far from where you live. A girl is much more likely to come home with you at the end of the night if your place is a 10 minute walk than if you have to drive or Uber across town to get there. Plus, being in your neighborhood, hopefully you’ll feel in your element and comfortable.

On a related note, pick a place where you’ve been before if at all possible. I’ve had first dates where I’ve decided to try a new place for the first time, and sometimes it hasn’t worked to my advantage. You don’t want to accidentally end up somewhere that’s so loud you can’t hear each other talk, so crowded you have to wait 30 minutes or longer just to get a seat, or on the other end of the spectrum, so empty that the bartenders can hear every word you say.

The ideal place is somewhere that’s lively but not too loud and within a 10 minute walk of your place. If you live in the suburbs or a part of your city where you can’t walk to any bars, maybe substitute 5 minute drive for 10 minute walk. But ideally you’re living in a place with at least one cool bar within walking distance.

4. Choose your seating arrangements carefully

If at all possible, don’t sit across from your date at a table. If you’re sitting at a booth, I’d recommend sitting on the same side. Sitting at the bar or at a hightop table also works. If you have to sit at a normal table, sit on adjacent sides, rather than across the table.

If a girl gives you shit for it (rarely happens in my experience), just say that sitting across from each other feels too much like a business meeting or job interview. As for why it’s so important to pick your seating arrangements carefully, read on for my next point.

5. Introduce physical touch early in the date

In the seduction community, this is referred to as “kino.” The idea is you want to start getting your date comfortable with physical touch early on so that making out and then having sex will just feel like natural progressions of what you’ve already been doing. If you don’t touch her during the date and then go in for a kiss at the end, making out and having sex might feel like too big of a jump and your date might be hesitant to do that.

Of course, it’s important to say that if your date shows discomfort with being touched by pulling away from you or especially if she tells you not to, that’s a sign that you should stop right away. Maybe you haven’t built enough comfort and/or attraction yet and you just need to give it more time. Or maybe it’s sign that things aren’t going to go anywhere with this particular girl. That’s ok too – plenty of fish in the sea. Whatever happens, you don’t want to cross the line into anything that could be construed as harassment.

But if the date is going well, chances are she’ll actually enjoy some playful touching. I usually start out with some light touches on the arm and hand if the girl I’m on a date with says something funny or interesting. Then if it seems like we’re hitting it off, I’ll move on to touching her on the thigh and holding her hand. Again, it’s important to read the signals you’re getting from her so that you can be certain she’s into it and take a step back if she’s not.

6. Don’t let the conversation die

Awkward silences can kill the momentum of a date and therefore kill your chances at having sex on that date. Now, I know this is a hard one to fix. It’s not as simple as choosing the right bar or wearing the right shirt. But I do have some tricks that have worked for me.

The first is to ask lots of questions. Most girls love talking about themselves and love it when guys are interested in them. If you feel like you’re running out of things to say, ask her a question about something she mentioned earlier in the conversation, something you remember from her dating app profile, or something about mutual friends, mutual interests, etc. You’ll take the pressure off of yourself to think of something to say, and chances are you’ll want to respond to something she says when answering your questions, which will keep the conversation going.

Also, listen carefully to her. I know sometimes guys get nervous on a first date and don’t always pay close attention to what their date is saying. But if you’re listening carefully, you’ll notice things that you have in common, things you’re curious to learn more about, and things that you also have cool stories to share about.

Finally, come prepared. If you’re constantly running out of things to say, it might be a sign that your life isn’t interesting enough or your opinions aren’t thoughtful enough. I know this was the case with me when I was in college. Now, this isn’t something you can fix overnight or even in a few weeks. But the best time to start working on it is now. If your budget allows, start traveling more and developing new hobbies. And if you don’t have the money right now to travel, start reading more books, listening to interesting podcasts, and doing free things around your city. Do whatever you can to make yourself more worldly and interesting so you can keep a conversation going with anyone.

7. Invite her back to your place with confidence

This sounds simple enough, right? Yet I hear from a lot of guys that this is a tripping point for them. They get so nervous when it comes time to invite a girl home that they either don’t do it or do it in such a weak, underconfident way that their date inevitably declines. There are a couple key rules to follow to invite a girl back home successfully. Well, one is a rule and the other is more of a guideline.

The main rule is that you have to ask her with confidence. If you’re tripping over your words and taking forever to get to the point, it’s probably not going to go well for you. Here’s why. By going over to a guy’s place on the first date, a girl is taking a risk. She really doesn’t know you that well yet, so there’s still a risk that you’re actually a creep or worse. Now, the risk of something crazy like you being a serial killer is pretty small. But there is a much larger risk of something less bad happening. Maybe you’ll push too hard for sex (more on that later), maybe you’ll have obnoxious roommates, or maybe she’ll develop feelings and you’ll never call again. And even if none of that happens, there is still unfortunately a bias in society against women who have casual sex. Unless the girl you’re seeing is completely accepting of herself and her desires, she’ll probably be at least a little hesitant to sleep with a guy on the first date for fear of judgement. And even if no one else finds out, that judgement can still come from herself.

So you’ll need to be confident enough to overcome any of her hesitations. If you seem uncertain about whether it’s a good idea, she’ll be even more uncertain and will likely decline your invitation. If you seem confident, she might still be a little uncertain, but your confidence should be enough to overcome that in most cases.

The second rule, actually a guideline, is to have a reason for inviting her back to your place. This can be anything from “I have a great bottle of wine at my house, why don’t we go back and have a glass” to “Let’s go back to my place and watch an episode of that TV show we were talking about.” This will help the girl you’re seeing to rationalize her decision to go back to your place. As I talked about earlier, our society judges women who have casual sex more harshly than men. So it’ll help if you can give your date a story to tell herself about why she’s going back to your place that doesn’t involve sex. But like I said, it’s only a guideline, not a rule. If she’s really into you and if you’re really confident, you don’t need to make up a reason. Just say that you’d love to keep hanging out with her back at your place for a little while. Again, this is where logistics really start mattering. It’s a lot easier to convince her to talk a 5-10 minute walk with you than it is to convince her to take a 30-40 minute drive or Uber ride across the city.

8. Don’t be afraid to escalate

I’ll preface this one by adding a disclaimer. If your date indicates that she wants you to back off, verbally or nonverbally, it’s important that you listen. First and foremost, you don’t want to sexually harass anyone. That goes without saying. And you also don’t want to ruin you shot at a second date just because she doesn’t want to have sex on the first date.

How quickly to escalate once you get back to your place depends on the situation. If you’ve been doing a lot of touching, hand holding, and even some kissing before getting back to your place and the sexual tension is through the roof, there’s a good chance it’ll happen immediately. Head straight to your bedroom and start making out and taking her clothes off right away.

But sometimes this isn’t the case. Maybe the girl you’re seeing is more reserved. Maybe you haven’t built quite enough attraction to start escalating right away. In that case, you’ll have to take things a bit slower. Pour a couple drinks if you want to do another round. If you’re already feeling good drink-wise, put on a show or just hang out and keep talking. If you have a yard or balcony and the weather’s nice, go hang out there for a little while. And at this point, it’s absolutely critical that you move forward with the “kino” I described earlier in the piece. Hold her hand, put your arm around her, caress her thigh. If she’s into it, you’re moving in the right direction. Then once you’ve built up a little more comfort and attraction, go in for the kiss. Once you’ve been kissing for a little bit, lead her to your bedroom and start escalating.

9. Expect last minute resistance (LMR)

So let’s say you’ve successfully invited a girl back to your place and gotten her topless in your bed. Sex is a sure thing, right? Not so fast. There have been plenty of times when I’ve gotten to this point with a girl only to have her say no when I reach to unbutton her pants. Why is this? Well, as I’ve mentioned, society doesn’t always judge women who have sex on the first date too kindly. This is incredibly unfortunate and one of the things I hate about our society. I’ll probably do another post on that later. But in any case, that’s how things are for now.

So plenty of girls go on first dates with an ironclad rule that they will not be having sex that night. If they’re into you, they’ll happily get almost naked in your bed, but they won’t go all the way. In other cases, maybe the girl has some kind of hangup about having sex on the first date, but it’s not an ironclad rule. Problem is, it’s impossible to know what the case is when you first get the LMR. So here’s what I’d recommend. If you get LMR, don’t make a big deal about it. If she doesn’t want to have sex, just accept it and go back to talking, watching TV, or whatever you were doing. Don’t get mad or try to kick her out. If anything, suggest that she stay over at your place anyways. If she’s in the first group, you won’t be having sex that night, but there’s a good chance it’ll happen on the second date so you don’t want to fuck things up. But if she’s in the second group, there’s a decent chance you’ll still be able to fuck her that night. I’ve had it happen a few times where a girl has said no to sex but I’ve invited her to stay over at my place anyways because it was late at night. And sure enough, as soon as we’re in bed with the lights off, we start making out and we’re fucking before I know it.

10. Don’t fuck up the details

Let’s say you’ve just had a great first date, she’s super into you, you’re on your way back to your place, and you can tell she’s ready to have sex with you. You wouldn’t want to ruin that because you forgot to take care of some details.

The most obvious thing: have condoms on hand. If you’re going back to your place, that means having a few in your bedside table or somewhere else you can easily reach. If you’re in a new city or think you might end up at her place, have a couple in your back pocket.

Also, clean up your place before you leave for a date. Used condoms in the trashcan or a Fleshlight laying around the bathroom can kill the vibe in seconds. And try to have an extra toothbrush on hand at all times. It’ll really help if you’re trying to convince a girl to stay the night with you.

Final Thoughts

I think this list should give you a solid starting point. If you follow all the advice here, there’s a great chance your next first date will end successfully. But it’s hardly an exhaustive list. Keep an eye out for more content around successful first dates, and more stories of some of my most memorable first dates.

 

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