So now you’re at the bar with her.


I like to start off by just rambling for a bit but be sure to keep your energy level up. I’ve found that I have to limit myself to one date a week to avoid getting burned out. It’s a good problem to have, but a problem none the less.


If it’s a Tinder date, I’ll usually ask her how many Tinder dates she’s been on.  About half will tell the truth and half will say a low number less than 10. I’ll usually respond with a joke such as, “Yeah, I’ve only been on like 3-4… this week.” And then laugh, tell her I’m just kidding, and give a playful touch on the arm.


Don’t underestimate the small talk. It builds comfort and makes you seem like a normal human being. Do it early and get it out of the way. Ask basic questions like if she grew up in the area, where she went to school, where she likes to go out and what she likes about the city, where she’s traveled recently or wants to travel. Remember the most important thing is that you have a fun energy about you. Your positive vibe and playful mood will rub off on her. Smile, laugh, and show general interest in the conversation. This is why I have to limit myself to 1 date a week. I simply don’t have the energy or drive to give the same kind of performance multiple times a week.


Once I’ve bullshitted around in this manner for 15 minutes or so I’ll bring out one of my first date games. I heard about this somewhere years back and have added little things to it over time.


I’ll say, “So we’re gonna play a game. I’m going to ask you a question. You answer it. And then I have to answer the same question I just asked you. And then you’ll do the same. But it has to be an interesting question. You know edgy and inappropriate. You can’t ask something boring like what’s your favorite color. Oh and you get one pass if you don’t want to answer a question, so use it wisely. Oh and you have to go first.


It can be a little wordy to deliver, but I’ve used this first date game more times than I can count and it’s always served me well. The key here is not putting too much pressure on when you explain it. Have a laid back smile on your face. You don’t want to come off too serious and make it sound like an intense lightning round of interview questions. Don’t feel like you have to stick to the game the whole time either. Keep a list of interesting questions in your head, but let the conversation flow organically and let this game serve as a kind of conversational foundation. It’s actually important to go off on tangents and have mini-conversations that will pop up as a result of the game.


Sometimes she’ll insist that you go first because she can’t think of anything. It’s not a big deal, just go first so she can get an idea of what kinds of questions you have in mind. I always start with the same question.


“So where’s the craziest place you’ve ever had sex?”


Don’t be afraid to ask this. You’ll be amazed at how many girls will gladly open up to you about their sex lives. In my experience, it’s about 95% who eagerly open up to this question. It’s important to start talking about sex and this is a great way to start. Let’s just hope you’ve got a decent story when the question comes back at you. 


A few other questions I like to ask:


“What’s something adventurous you’ve done in the last year?”


“As a kid, what did you want to be when you grew up?


“If you could max out your credit card at one place where would it be?”


“If you could have sex with someone in this bar who would it be? I mean, besides me of course.”


“Celebrity Marry, Fuck, Kill.. Go.”


“If you could have dinner with any two people dead or alive who would it be?”


“If you could live anywhere for a year where would you live?”


“What’s one thing on your bucket list?”


“If you were stranded on an island, what’s the one alcoholic drink you’d want with you?”


“What’s one TV show or movie you couldn’t live without?”


“What’s something you’re passionate about. Something you’re into or know more about than the average person?”


“If you could be famous for something what would it be?”


“If you were going to apply to a reality TV show which would it be?”


I usually only end up asking half of these. The conversation will go off in all different directions throughout the game so I usually don’t have time to ask more than 6 or 7. Then of course we’re going back and forth so she’s asking questions as well.


About 5% of girls will not want to play. They’re usually just bad at thinking of an interesting question on the spot. No worries, don’t push it too hard. Just act like you’re abandoning the game but then sprinkle these same questions throughout the conversation.


One other game I like to play is the 5 questions game. I’ve used this countless times to get a kiss on the cheek. If she wins, she gets a drink and if I win, I get a kiss on the cheek. Watch the old pro play the 5 questions game here.

You can tell a lot about how the date is going based on how she kisses your cheek. After about an hour and half, get the check and tip well. Especially if it’s a bar you frequent.




At some point during the date, you should have planted a seed in her mind about going back to your place. Here are a few I use:


  • A TV show that you like that she hasn’t seen, a show you both have seen and like, or a show that she likes that you haven’t seen. The questions mentioned above can help you get on the topic of TV shows. Talk up some show and casually say, “We’ll watch it sometime.” or “We’ll have to watch it soon.”
  • The most amazing bottle of wine or champagne that ever existed. She hasn’t lived until she’s tried this wine. You don’t have to tell her that it’s Trader Joe’s poured into a decanter. This also works with liquor if she mentioned a certain kind that she likes.
  • Music videos. At some point maybe you talked about the most badass music video that recently came out. And it just wouldn’t be right if the night ended before the two of you sat down to watch the latest video of Nicki Minaj twerking her massive ass.

I tend to go with some combination of the above. As we leave the date, I extend my arm for her to hook her arm through mine. I’ll mention that it’s slippery out and I would just hate for her to slip and fall. Be sure you walk on the side closest to the street so it appears you have some social intelligence. That’s when I hit her with, “So we should go watch X TV show, there’s a really hilarious episode I think you’d like” or something to that effect. This works about 90% of the time. Probably more like 95%. Girls just seem to know the deal these days. If she doesn’t want to come inside, I just say, “Ok that’s fine, you were a fun date tonight.” It’s not worth pushing it. There’s probably more you can do to better your chances, but I honestly don’t sweat it. If one girl doesn’t want to come inside, I know the next 9 will. Just get this one harder-to-get girl out on a 2nd date. You may have just stumbled across a keeper. 


If she does come inside, this means there’s a 95% chance you can at least make out with her. I have an elevator in my building that takes us up to my apartment so when we get in I say, “You know what I love doing in elevators?” Then I tilt her chin up with my curled index finger and kiss her. At this point though, she’s expecting to make out with you so you really don’t even need a clever line. Just take your curled index finger and tilt her head up with a smirk on your face and bring her head towards yours.


The rest is beyond the scope of this post. Good luck out there and let me know in the comments section how it works out for you. Now go have the best first date. 

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