Dating is tough. Not dating in the “meet someone amazing, like them immediately, and be attracted to each other forever” kind of tough, but more of a frivolous, superficial waste of free time and hard-earned spending money. Let me be the first to admit that if getting down is on the table, I am a hell of a lot more willing to shell out $50-60 on dinner and drinks. This is not me being a pig, misogynistic, or even picky in my choice of lady; it’s purely financial, as my average bar tab is way south of twenty bucks a night (I sneak in shooters everywhere). I’m always on the lookout though: once I finally do meet a girl whose juice is worth the squeeze, I can’t wait to take her out to the nicest restaurant I can afford, as every little boy dreams about the perfect date with the perfect girl. Here are a few more tips I’ve learned along the way:
1. You better be able to sing if you try karaoke. Not to go all Eminem on you right off the bat, but you only got one shot at this. She likes the confidence, but you better not embarrass yourself. Know your one good song and stick with it. For example, mine is “Piano Man” by Billy Joel.
2. Eight o’clock at a “lounge.” Not yet scientifically proven, but 8 p.m. is the best time possible, and lounge chair couches near a fireplace are a perfect setting to pretend that you both are classy as fuck.
3. You’re paying. You asked her out, and she agreed to block off a Friday or Saturday night, so you are on the hook for whatever she eats and a couple drinks. If she has any awareness at all, she will probably buy you a drink or two after you guys head to the next bar after dinner.
4. Recommend that you two hit a bar after dinner. You two just had a lovely sit-down meal, she’s having a great time, so why not let the good times roll? If you’re really in the zone, you’ll be able to pull this off while sounding spontaneous and full of adventure. No expectations, though.
5. Pinch the side of her elbow whenever you get up from your seat, and gently squeeze between her shoulder and neck whenever you come over behind her to sit down. I have zero psychological literature to back this up, but it works. Maybe something to do with her dad?
6. Never make plans with someone that will last longer than you’ve known them. I know celebrating your birthdays together in Vegas come October sounds like an awesome time, but the two of you just met last week. Pump the brakes.
7. Play it cool. At some point during the date, shit won’t go your way. Maybe she bumps into a guy friend and ends up chatting him up for a half hour, or is peeking at her phone three too many times, something weird like that. It doesn’t matter though. James Bond wouldn’t care, and neither should you. Do not show any outward signs of distress or agitation. You’ve got this.
8. Funny is another word for clever. Girls like clever. Evolutionarily, women are hardwired to like intelligent men, because being able to outsmart giant man-eating predators with a wife and kids in tow gave you an edge way back when. Make her laugh and she’ll be into it.
9. Don’t look at other girls in the bar. Yes, it’s rude, but you’re wasting your time anyways. It’s the dimmer lighting that makes them look more attractive, not your beer goggles.
10. Meet her at the restaurant. Yes I know, on the third date you’re supposed to pick her up, but this is not a third date. You deserve to have the option of leaving and you also have the option of offering to “split a cab home.”
11. Girls don’t like it when you refer to yourself as a ‘bro.’ It’s a reminder of all the douchey frat guys who screwed them over in college. Sorry, bro.
12. Do not try to play dress up. Some guys throw on a blazer and suddenly look like they’re attending eighth grade formal. Throw on a cool tee shirt under a jacket if you can’t pull off an actual look. This at least says, “I wanna be formal, but I’m here to party too.” If she doesn’t like it, just ditch her.
13. Eddy Bauer. Something about those long sleeve XLTs rolled up to a guy’s elbow just does the trick.
14. Match your beard stubble and haircut to your shirt color. Stay with me here. Fact: facial stubble is scientifically the most attractive look, says Tom Brady (probably). Here’s what you do: grow out your facial hair for a week, get a 1-2 fade, and throw on a grey XLT with dark blue jeans and dark black shoes. Similar color coordination for brown haired guys. You’re welcome.
15. Have your talking points ready. “Never have I ever…,” “Would you rather…?” “Tell me about your favorite vacation,” etc. Don’t be a putz; if a lull in the conversation persists, just fire one of these out of a canon. Be charming about it. Think Zach Galifanakis from In Between Two Ferns.
16. One squirt of cologne is enough. She should only be able to smell you if she hugs you or better, not from across the table.
17. Hold that eye contact. Girls know how to test a guy, and your stock rises with every extra half second your eyes remain locked on hers. She knows you’re squirming inside, so stay calm. Try to flip the tables a little bit by cracking a smirk, squinting your eyes playfully, and turning your face slightly to one side, all in one fluid motion.
18. Water is a decent solution for bad breath. Bad breath comes from particles on your tongue, which can be washed away with a little H2O. If you’re caught without mints, just order a water on the side and pound it like you are at your first ever college party freshman year. Ignore her incredulous looks, and simply shrug your shoulders. You just bought yourself an hour, but go tip the bathroom guy for some mints.
19. Do not talk about your work unless she specifically asks what you do and seems interested. There is nothing worse than talking about the bar when you’re at work and talking about work when you’re at the bar.
20. “It’s our imperfections that make us beautiful”. Work this seamlessly into the conversation at least twice. You’ll thank me later..
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