When I was in college, it wasn’t a big part of the culture to have a  1-on-1 date with a girl that you recently met. It happened occasionally, but usually the best way to get to know girls was to just show up to a house party or the bar. Dates were something that people in serious relationships did.


But then one day you graduate out of that community and find yourself in the real world. And you watch as the social circle you once knew and your place within it evaporates into thin air.


This phenomenon paired with Tinder gives rise to the binge-dating apocalypse millennials find themselves in today. I’ve been on over 100 dates in the last 3 and a half years since I graduated from college. And like anything that you repeat over and over and over, you start to get good at it.  After awhile, you start to recognize what works well and what doesn’t.  You learn from your mistakes and make note of the things you can repeat that will lead to success.


Here are the 7 biggest mistakes that I’ve made, and that I see other men make on first dates.


Preventing The Flake

flakey girl


You meet a girl. You get her number. You get her to agree to a date.


If you think there’s no more work to do between said agreement and the moment the date is supposed to begin, you’d be very wrong.


Flaking is at an all-time high in the modern dating scene, especially if you meet online and have yet to actually meet in person. You’ll need to keep in touch and continue to build comfort during the period of time between the date agreement and the actual date.


If you don’t, you can expect her to suddenly feel very ill the day you’re supposed to meet. Or perhaps her best friend just broke up with her boyfriend and is so devastated that she has to spend time with her instead. Or she might just disappear off the face of the earth and never text you back at all.


These scenarios can all be prevented by sending her a few texts, or even better, send her a few Snapchats that will make her feel more attracted to you and comfortable with you.


A Lunch Date, Coffee Date, Or Adventure Date



There’s a series on Netflix called Easy. In one of the episodes a twenty-something girl shares her experience with going on dates with men she meets through Tinder. She’s been on 4 dates. 2 of them were over coffee and the other 2 were drinks dates.


One morning over a gossipy brunch, she confides in her friend that she had sex on the first date with the two men she met for drinks while the coffee dates didn’t really go anywhere. She goes on to say, “That’s the difference between a drinks date and a coffee date”. And she’s exactly right.


Don’t forget about the world’s original hookup app: alcohol.


Why waste your time meeting a girl in the afternoon only to warm her up for the guy who will be banging her later that night? Save the lunch/coffee/adventure dates for later on down the road once you’ve determined if she’s actually a girl you’d like to spend quality time with and get to know further.


Dinner Or A Movie



Most guys have probably figured this out by now. But sitting in a dark theater where you can’t really talk to your date is not a good way to create chemistry or get her to open up to you. We’re not in middle school anymore – ditch the movie theater.


Additionally, buying her dinner is an unnecessary move and you should avoid it if at all possible. My ideal date time is 8:30 P.M. That way we’ve both likely had dinner already so we won’t stuff our faces with food and feel bloated, killing any sensual vibe that we may of had.


Not to mention I’ve saved thousands of dollars over the last few years sticking to drinks only. Again, save this type of date for girls who have earned it.


Sitting Across The Table From One Another



Another conventional first date norm that makes it difficult to establish chemistry is sitting across from each other like it’s an interview. In this setting, you can’t lightly touch her on the arm to express a point.


Even a three-second pause in conversation will cause awkwardness. And you must have ultra-keen awareness of eye contact, walking a fine line between not enough eye contact to build a connection, and too much eye contact that it makes the date feel intense.  Sitting side by side in bar stools solves all of those problems.


Not Mentioning Sex



This is probably the most important aspect of all. It’s imperative you have some kind of conversation about sex or dating while you’re with her. If you don’t, the entire interaction will be a boring, platonic, sterile back-and-forth fit for an office break room. You might feel weird talking about sex with someone you just met – and it’s important you do it correctly. But it’s a pretty easy thing to get over once you’re used to it. You just need a smooth transition. You don’t want to come off like some notorious guys on Tinder who just blurt out sexual statements before any comfort is established.


After you’ve had friendly chat for 20 minutes or so, it’s time to introduce a more sensual vibe. I like to start by playing the “Crazy Questions Game” where I ask, “So where’s the craziest place you’ve ever had sex”. You might be amazed how readily she will open up and answer this question.


And here’s the thing –  once you get her talking about sex, she’ll start feeling much more comfortable with you and the walls will come down. You’re no longer just some stranger. You’re a guy she’s opening up to and sharing her most intimate experiences with. Talking about sex with you achieves a similar level of comfort she needs to actually have sex with you. A nifty little psychological thing if I must say.


Forgetting to Touch



How many movies have you seen where a guy goes for a kiss at the end of the date and it’s completely awkward and she gives him the head turn? This is because he’s going from zero touching to trying to kiss her on the mouth all in a span of about 3 seconds.


Let me explain the correct way to go about this. It all starts with a little touch on the forearm 15 minutes into the date. You express some emotion or react to something and say “No way, me too!” or “Haha I can’t believe that!” or “No you can’t be serious!” As you say this you touch her arm while maintaining eye contact.


You do this a couple times throughout the date and eventually start to lightly touch her thigh instead of her arm as you express your emotions. Then you make fun of her for being basic and wearing a Michael Kors watch. You’re holding her wrist and examining the watch but really it’s just another excuse to touch.


Then you make some kind of bet with her and tell her if you win you get a kiss on the cheek. If you’ve managed to do all this then by the end of the night a real kiss will feel like the most natural thing in the world. Many times, you’ll be able go for quick little makeouts right there on the date as you’re sitting next to her.


Not Having An Endgame



You always should have plan for what happens next. Ideally, you want to get her back to your place on the first date. You should always at least try so you can find out if she’s the type of girl who has sex on the first date or if she makes guys work for her a little more. So your first dates should probably occur at whatever bar is closest to where you’re sleeping that night.

During the date, you’ll want to “seed” a reason to go back to your place. At some point in the date, I’ll bring up television shows that I’m into and tell her how amazing some show is. After we’ve had an exhilarating conversation about the newest HBO mini-series, I’ll tell her “we’ll have to watch it sometime…” as I playfully tap her thigh with the back of my hand.



I think it’s safe to disregard most of the conventional dating advice you hear from mainstream television and media organizations. Instead, find men who have been getting the results you’d like to have and then just do what they do.


Sometimes I wonder if a bunch of people got together a long time ago and conspired to make conventional dating advice as counterproductive as they possibly could. It seems that when we’re young, almost all “well-rounded” men follow the abysmal timid nice-guy advice that ends up just getting us screwed over. Meanwhile the hounds and scoundrels are slaying it.


Part of becoming a man in the 21st century is realizing how full of shit most “conventional wisdom” is as you go through life and learn from your experiences. Fortunately, the internet has served as a place for people to come and compare notes and build more pragmatic wisdom from the ground up rather than just blindly taking the advice of well-connected “experts” from the top down.


Read Next: The Best First Date Guide Pt. 1


30 Best Texts of All-Time

If you enjoyed this post, get updates and your free copy of The 30 Best Texts Of All-Time

We respect your privacy.