First Date 101

I won’t sit here and feed you a bunch of crap about how I’m an expert on dating. No one is an expert on dating and if you claim to be, you’re a moron. Starting a relationship is hard. I mean, we think that the hardest part is actually asking her out… But then we do and we come face to face with the real challenge – Keeping her interested.

First dates are difficult. Period. That’s how it is. They’re not supposed to be easy. It’s only easy once you get to know each other and your likes and dislikes. First dates are when you’re still learning about each other and so you’re going to make some mistakes. It’s inevitable. However, if you keep these things in mind, it’s bound to be 10x better in the short and long run.

1. First dates are casual – I can’t tell you how many times I’ve seen this get broken. At the first date level, you’re not a couple. You’re two people who are mildly attracted to each other and seeing where it goes. By this logic, you don’t go all out and blow a whole paycheck on the date. You don’t go to the fanciest restaurant in town. You don’t buy her a $50 bouquet of flowers. You do something cheap, but still fun. My go-to first date activity? Bowling. It’s relatively cheap, it’s fun and even if you suck at it, you can play it cool like you’re letting her win. If it works for me, you can pull it off too.

2. Do NOT eat fast food – If you do, it better be a local burger joint that has the best damn food in a 100 mile radius and she’s never been there (or she suggested it). McyD’s, Taco Hell, etc- these are not date places. Hell, these are places you shouldn’t be eating at period! But that’s another rant. Go to Applebee’s, Cheddar’s, Ruby Tuesday’s, TGI Friday’s. Somewhere decent, but you can both dine for under $45 (not including tip).


3. Do NOT go overboard with the cologne – Seriously guys, I know your grandpa was cool with his aftershave when you were a kid, and a little is ok. But spraying a layer of AXE on every inch of exposed skin is over kill (in a bad way- Sorry Colonel Hannibal Smith). A little goes a long way.

4. Pay for the meal – I know I said to not go all out, but really it’s just plain rude if you don’t. Any woman who’s looking for a real relationship today will tell you that they would like for the man to at least offer to pay for the meal.

5. Tip your wait-staff well – Nothing makes a guy look worse than buying a decent meal and then skimping on the tip. Don’t be that cheapo. It makes you look cheap and uncaring towards others who work hard.

6. Dress nice, but still be you – By this I mean, wear your style; but wear something nice. Don’t go out in faded jeans with more holes than a Louis Sachar novel. (google it if you don’t get the reference). I’m not saying wear a suit and tie. But look decent. Shave the stubble, groom the beard, pluck the uni-brow, brush those teeth. Be presentable. And by all means, cut your damn fingernails.


7. Be Confident – This is bigger than you can imagine. Confidence is something that we recognize on other people at a primal level. And she’ll be able to tell if you are or not. A man who is a 5 can land a 9 if he is truly confident in himself. Easier said than done, I know. One big tip on being confident is this. And it’s so simple, you’ll kick yourself for never thinking of it before. All those issues you see in yourself, she’ll likely not see. You spend 24/7/365 with yourself. That’s why they stick out to you. She is going to spend at most 5 hours with you. It’s doubtful she’ll pick up on anything physical that’s going to turn her away from you. She said yes after all, that means she’s at least interested.

8. Don’t go to the movies – It’s kinda awkward and you both leave the theater knowing nothing more about the other person than when you walked in.

9. Listen to her – This should really go without saying, but here goes. Listen to what she says. Don’t just hope to god that you get laid eventually by her and don’t ignore her to think of how attractive you find her. Fantasize about that later. Look her in the eyes, reciprocate the conversation.

10. Open doors for her – I’m really big on old fashioned etiquette. I open doors for women, help them get seated, help them out of the car- the whole spiel. Women pay attention to things like that.

11. Do not be over attached – This is another big one and it ties in with the very first rule (dates being casual). Clingy doesn’t portray confidence. Pretty much end of story. And for the love of Jehoshaphat, do not tell her that you love her. Adulthood isn’t high school anymore. You don’t love her (even if you think you do) and she certainly doesn’t love you (even if she thinks she does). That is something that takes time to cultivate and bloom.

12. The Kiss – This is something you just have to play by ear. Me being old fashioned, I rarely kiss on the first date just out of principle. However, it all just depends on your individual situation. If you think she wants to kiss, go for it. If the evening went well beforehand, the worst that can happen is she’ll stop you and tell you that she would like to wait. If the evening didn’t go well, hopefully you’ve got the common sense to recognize that and not even attempt the kiss at all.


To sum it up, first dates aren’t nearly as big of a deal as a lot of people make them out to be. Keep a conversation going, do something fun, get some food and be casual. Be yourself. Don’t try to impress her, and don’t be cocky. Just be confident in yourself. I can’t guarantee that these rules will land you a relationship, but they’re a step in the right direction.


– Cameron Blevins

Follow me: @CamOnAir