Guys. First Dates. We’re Doing Them Wrong

I recently botched a first date, which is appalling. I am fantastic at first dates. In the past two years, I can only recall one or two times a girl turned me down for a followup. And second dates are a must, because they get you a momentous step closer to seeing girls in their underwear. Girls look hot in underwear.

How did I screw up? Well at first I couldn’t figure it out. I did everything right. Showed up on time. Wore a suit. Picked up the check. Waited with her as she hailed a cab. By every respectable metric, I scored mad points.

Which is the problem. I did everything she expected a guy to do. There was nothing differentiating me from the endless supply of cordial, tepid staffer drones populating this city.

Anyone can try and be a perfect gentleman. Let me throw my madras coat over your bare shoulders to protect you from this chill. There’s nothing endearing or enjoyable about that. And if the 90s taught us anything, it’s that trying is lame.

But it’s not just that. This is 2012. We have molecular gastronomy and black presidents and your phone can double as a flashlight. Conventions and norms are out.

Which is why everything guys are doing on first dates is wrong.


You’re selecting a place you think the girl will like: Fuck that. Everyone these days is deferential and polite. You are allergic to Thai food? We can just avoid Chinatown altogether. Why present yourself as an effete pushover before ever meeting someone?

No. Instead, don’t take any of her recommendations into account. In fact, don’t even solicit suggestions. When she asks what the plan is just text back “Martinis and pork belly.” She’ll be in awe of your brusque nature.

You’re shaving beforehand: Oh, you took the time to present your best face before this date? You’re already in trouble, because now she knows you are trying to impress her. And there’s nothing girls like less than guys who like them. You’d have a better chance showing up with a construction paper card stating your affection.

Instead, shave three days before. You’ll look like a cowboy or someone working undercover to infiltrate a terrorist organization. Plus, not shaving will mess with her head, putting into it a torrent of self-doubt. Does he not care?

You’re having a drink beforehand: Look at you, all cool and liquor-suave and loquacious. You’re so charming. That’s exactly what she’ll be thinking. Or, she’ll think you were so nervous you couldn’t arrive before putting back a cocktail. No, show up as sober as a horse—or any other teeotaling animal. If you need a vice to calm yourself, have a cigarette. It will baffle her. Why would he smoke before meeting me. That’s so rude. Because it’s about doing the unexpected.

And lest you think a woman would never date a man who smokes, remember, every girl loves doing things that will cause her to hate herself later in life.

You’re arriving on time: Do you have any idea what this says about you? Oh, hi. I was so excited for this date that I rearranged my entire day just to be punctual. No. Show up eighteen minutes late and she begins to think you aren’t interested. Appear frazzled when you arrive. Sorry, this, a client called, panicking and I just had to rearrange a ton of funds or—well, sorry. Never mind. Who cares if you don’t have clients? You should have clients. Women are insatiably attracted to men in the finance industry.

Then, after a moment, appear to noticeably calm down while looking at her. She will think it’s her presence that is easing you, which plays to her nurturing side.

You’re suggesting a second drink: Never do this. So what if you could sip sidecars in a corner booth with her for hours? That’s fucking adorable. But making a girl doubt herself is the quickest way into her pants. And if you don’t bring up another drink, just calmly staring as she swirls her slowly melting ice with a straw, she will internally freak out. Then it’ll be her hesitantly suggesting a continuation of the date.

To which you can warmly and affirmatively reply.

You’re automatically grabbing the check: At some point a bill will be placed on your table. The gentlemanly action is to grab it immediately so your date need not worry. You’re also supposed to stifle any effort she makes to contribute funds. Stop putting your dates at ease. Instead, let that little black folio sit there for a minute, screaming its presence. Then when she seems about to burst—women can’t stand clutter or unresolved situations—say this.

“Rock, paper, scissors?”

“What?” will be the reflexive reply.

“Rock, paper, scissors. For the check.”

She’ll be confused but pensively agree to it. If you lose, grab the check with an obviously fake sigh. But if you win, grab the check and say “I won. I get to pay.”

Look how funny and cool and different you just made yourself. Plus, the relief she feels from not paying will send endorphins and adrenaline cursing through her system. She will be screaming for sex by the time the waiter comes to pick up the bill.

You’re paying with a credit card: No one has cash these days. So pick some up before your date and throw down a fat wad on top of the receipt. When she looks askance at the action, tell her you just sold a gram of MDMA to the Secretary of Defense. She won’t believe you at first, but after a while, well, where else could all that money come from?

If she asks, smile, and tell her you’ll tell her some other time.

Boom. Second date acquired.

65 Thoughts on “Guys. First Dates. We’re Doing Them Wrong

  1. “You’d have a better chance showing up with a construction paper card stating your affection.”

    It should read, “I will ignore you, but you will still put out. I know, because I’m a doctor.”

  2. Anonymous on January 13, 2013 at 4:38 pm said:

    women do not like guys in finance.

  3. Loving the rock paper scissors. I would die laughing if a guy pulled that– and definitely go for round two. Might even be a two-dates-in-one-night move.

  4. Veteran on December 6, 2012 at 5:20 pm said:

    It’s funny: over the last decade and a half there have been a lot of guys, some of who’ve made shit-tons of money off their insight, advising men on how to approach women, engage them, court them, land them, end up in LTRs with them, etc. Some of it was very, very useful: I personally really appreciated those guys urging other guys to simply go up and *talk* to them in social settings, advice many of us, me included, wouldn’t do prior to being given strategies or techniques openers to both engage them and tamp down down your own anxieties. Seriously, thanks to those dudes. Very helpful.

    Still, others tried to market their insight, some successfully, as a never-fail system in which a step-by-boring-step process was employed, or set of guidelines or rubric slavishly followed, all with the intent of reaching the goal: bedding the girl on the first, second date, what have you. All fine — that’s what I always want to do, too.

    But what it often leaves out is the opportunity for in-the-moment fun. Some guys get so focused on the rubric, or the goal that the rubric is supposed to result in, that they forget there’s an actual human being sitting across from the table from them, providing you an opportunity you’re missing because you’re already so dead-set about the goal. To employ a sports metaphor (because that’s all we dudes recognize, right?), that’s like thinking that simply knowing the rule of football will win you the game. It won’t.

    In my experience, guys make two huge mistakes when it comes to dating: thinking in terms of “systems” and “techniques” when it comes to engaging women, and thinking of it in terms of sheer “number of approaches,” that you bed women by simple attrition. Both assume that the woman isn’t an agent, with free will, in possession of her own mind which she uses to make decisions, etc. Focusing on the “system” or “rules” (which, by extension, means focusing on the end goal, seeing the ladies in their undies) means missing the opportunity for the unexpected fun of a new experience. In fact, my experience has been that if you go into the date with absolutely *no* expectations, or the pressure to fulfill them, if you think of it as simply an *opportunity*, you’ll surprise your self by how often things end up going your way (and by “your way,” I mean the whole “seeing-the-ladies-frilly-undergarments” thing). Women don’t want to go out with you because they want to be part of an experiment to see if something works. They want to go out with you to have fun. Why not look at the date as that kind of opportunity? But many men don’t.

    Second major failing: some guys can’t over getting rejected, not getting the number, not getting the second date, not geting to bed, particularly after they’ve employed some sort of “system.” “Why didn’t it work?” they ask themselves. Ever stop to think that perhaps you weren’t her type? If you actually listen to what women say, you’ll discover just as wide a variety of tastes and likes as yours, to be sure, but, just like you, women have preferences, deep-seated sometimes inexplicable ones that have to little do with what you can and cannot offer. There are many women who find Brad Pitt unattractive (“I could never be with a man who’s prettier than I am,” I heard a trusted female friend say when I broached the idea that she might find Mr. Jolie attractive). See what I’m saying? Sometimes the rejection isn’t about you at all, or it is in the sense that you just don’t *do it* for her. And that by no means intimates that you don’t *do it* for someone else. And yet that doesn’t stop men from wanting some sort of explanation, and being angered when it isn’t as clarifying as they might like. Guys, if a chick doesn’t like you, it may have little to do with anything you can change about yourself. You’ll be much healthier, and much more attractive, if you forgo the hurt angry feelings and move on.

    Third piece of advice: be passionate about something *other* than her. Find the thing you want to do (sport, cars, performance, what have you) and DO IT. Nothing’s more attractive to women than a guy who’s passionately in pursuit of something other than making her happy. Make yourself happy. With that, grows confidence, presence, power. Those are things women like.

    • Believe me, I get it. I mean, this is, in some form, an attempt to poke fun at that concept. There are definitely things you can do to “make yourself more attractive” but at the end of the day, the only way you things are going to work out is if you are yourself. Now, there is a lot of leeway in “who you are” and that’s where I think the fun can sometimes be when interactive with a variety of different people of the opposite sex. But thanks for the comment. Don’t disagree with anything you’ve said

    • This comment is full of win.

  5. I LOVE that Z used “butt hurt” – best show ever LOL.

    Also, I’m curious how many successful first dates Joseph has had….

  6. I like how butt hurt people are about this.

  7. This doesn’t make any sense to me.

    Wouldn’t you want to shave before a date to look good for your sake?

    Wouldn’t you want to arrive on time because that’s what common courtesy is?

    “Martinis and pork belly?” “Brusque nature?” Da fuq? That sounds like a great way to end a date before it even starts.

    I automatically grab the check because it’s classy. If my date wants to pay for half, she can pay for half. So what? Girls make money.

    If you are going so far out of your way to get laid that you’ll willingly degrade your own appearance or excuse yourself from simple conventions like punctuality, you have self-respect and security issues.

    Smoking? Seriously? Smoking is fucking gross. Period.

    This is like reading the epiphany of a 17-year old who just got rejected by the prom queen.

  8. Wowww, someone is bitter…

    You could do everything right or everything wrong on a date and nothing will guarantee a second date. She may like you, but there’s no chemistry. Maybe she didn’t like the way you looked at her or maybe you didn’t compliment her. There may be chemistry but you don’t have the same sense of humor, etc. It could be anything or everything. You should want to be yourself when you are around others (this goes for guys and girls), otherwise you are being fake. I agree that sometimes it is nice when a guy tries to impress a girl, but not beyond who they are as a person.

    You made a lot of assumptions, I don’t. Not every girl is the same and you can’t think that one way of “planning” the first date would work with everyone. I would just take everything that was done and said on the first date as being the truth. If someone is on time, great, because they followed up with what they said they were going to do. If they were late, they should tell the truth as to why.

    I think you are seriously over-analyzing everything just because you got rejected.

    If you ask a girl on a [first] date, you should pick up the check. I would think it childish and rude to suggest rock-paper-scissors unless maybe after a couple dates she starts to offer to pay (I don’t assume the guy will pay every time and I don’t think it is fair to assume so).

    You need to get over yourself. “I’m fantastic at first dates.” Oh, so you’re fantastic at being yourself? Or being fake? Everything you wrote sounds very superficial, I know some girls are superficial as well but you need to accept the fact that she just didn’t dig you. Even if you played the date out differently, you what…would have gotten one or two more dates before she realized she just wasn’t that into you? Why drag out the inevitable?

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  10. I might have to differ with this post, but only slightly. I think it’s because I’ve dated so many assholes in the past that I’m actually looking for a nice guy. Or whom I think is nice. My thoughts: be totally nice on the first date, which will make me think you’re the exception, then pull this stuff on date number two. I’ll be hooked for life.

  11. “Appear frazzled when you arrive. … Then, after a moment, appear to noticeably calm down while looking at her. She will think it’s her presence that is easing you, which plays to her nurturing side.”

    As seen in…every romantic comedy, ever. I approve. Tested, tried and true. The look it puts in her eye is one where you can tell her heart has actually fluttered. I live for that look. Carry on.

  12. The Rock Paper Scissors thing? PURE GENIUS. After 10 years with one guy I don’t even know what a date is anymore, but when I read that I knew it was gold. Also, the not shaving thing? So true. Guys look so much sexier with some stubble (those who can grow it. If it’s gross an straggly – e.g. most Asian guys – then go ahead and shave, please :P). Clean shaven faces make most of you look like babies.

    • Yea I stopped shaving in April. I’ve gone clean shaven three times since then. I look like I’m four. And I’ve never actually pulled the rock paper scissors, but damn. now I have to try it

  13. “Every girl loves doing things that will cause her to hate herself later in life.”

    This has sparked a conversation because it’s so utterly true. And the “rock, paper, scissors” is absolutely genius and I can’t think of a personality type which it wouldn’t woo. Is our gender really that universally predictable? I’d be putty at that it would intrigue me so, though perhaps publicly sharing your best moves could shoot you in the foot one day…

    • I’ll echo the rock, paper, scissors thing. Love it.

    • Ha. I’m sure this blog isn’t popular enough to prevent me from still using my “moves.” And yes to your first point. I don’t know how many girls have told me “I’ll never date a smoker” and then three weeks later “I can’t believe I’m dating a smoker”

  14. According to this, I’ve been doing it right. With the exception of being on time. I’m on time for dates, always. And also, I don’t trust myself with cash.

  15. Actually, I always have cash. But for those who can’t pay for the entire bill in cash, another option is to pay with a card, but tip in cash.

  16. This is so true

  17. “Even assholes need to be loved”. No. No they don’t.

  18. holly golightly on December 4, 2012 at 10:38 am said:

    i think you can only pick half of this list or you’re going to run the risk of being an asshole. unless of course, being an asshole is your authentic self.

    but. what some of this speaks to is giving a girl space to come towards you. when a guy is late, flustered, casual, distracted, sober or playful, you get a chance to observe him without all the focus being on you. You get a chance to get out of your own head and engage him at the edges, in the imperfect moment. You get to see if you feel comfortable with him, instead of trying to find your stride in contrast to his projected perfection.

    i love that scenario. because it gives me a more accurate read on how i feel. i get to be in the moment. and it’s more fun.

    that said, i hope anyone who uses these things just TO SEE WOMEN LOOK PRETTY IN THEIR UNDERWEAR burns in hell forever, but not before contracting annoying, itchy and horrifying STDS.

    BOYS. stop playing games to create ideal conditions for your nakedness. (Brett Hannons this means you.) Girls love to be naked too and we promise to take our panties off (if we even bother to wear them) in record time if you just show up as your charming self and be breathtakingly honest about who you are. I can write scripts if needed. (We should have a MGoM meetup for that. You pour out your true situation and we write you scripts on the spot.) Even assholes need to be loved.

    Okay, I’ve droned on long enough.

    • You can drone as much as you like. And yes, I have faked being flustered before.

      • As have I. Truth be told, in any given social situation, I’ve faked a number of emotions to elicit a desired reaction from my subject in order to achieve conveying a facet of my personality that may not have otherwise had a chance to be put on display. The frazzled-to-calm move is but one of a million. It’s sociological chess; I do this, you do that in response, so I get to do this, which is something I wanted to make sure you saw in the first place. 100% of the time, it works; people are predictable (which was the whole point of this blog post).

        • Yea. And it’s not like it’s the gigantic charade. It’s small subtle things. People do it in every aspect of polite society. What’s wrong with adding it to the dating game

          • I wouldn’t dig the frazzled stunt. I’d tell you to chill the fuck out. Y’all don’t deserve second dates if you’re going to be dramatic and fake.

    • The thing is, we can’t figure out if we’re interested in more than just getting you naked until after we do, in fact, get you naked. Because before that, it’s really all we can think about. I’m in love with every girl I spend 5 minutes flirting with, but that’s really just because of the allure of how sexy women are. Let us get that out of the way, then we can find out if we are interested in the rest.

      I think I regret typing that out.

      • I think there’s so truth, but I’ve definitely wanted to date girls before seeing them sans clothes

      • That actually makes perfect sense. It’s not how our brains work, but now that you’ve explained it I can completely understand men’s thought process being that way. So you’re advocating we all just strip down right away so as to not waste effort on guys who might not actually like our personalities? Truth be told you lay down a compelling argument for it, saving both sides time. Man, you and Brett make quite the team…

        • I mean, it really WOULD save time. Though you have to give us more than one chance before you judge our sack-game. We’re almost never our best on the first time, not to mention if you surprise us by giving it up earlier than we are expecting.

          There are totally exceptions to the rule. I’ve definitely wanted to date girls before seeing them naked… But, how can I really be sure that I wanted to date them and not just see them naked? That’s the whole mindfuck of being a dude… It’s nearly impossible to strip away (pun intended) the sex aspect of things from the compatibility/romance/emotion/whatever.

          • Ha. I’ve slept with one person my entire life so far be it from me to judge someone’s “sack-game.” At this point all I can do is file it under “different” at the most, right? The fact people are getting upset about this is almost as entertaining as the post itself. I don’t sit at work all day to come home and read about the fiscal cliff. I like to have a chuckle if possible. That being said, don’t knock Sheldon Cooper. I may or may not have a bright red t-shirt with nothing but a huge picture of his face on it that reads “Bazinga.”

    • modernwoman on December 4, 2012 at 6:01 pm said:

      chill out holly golightly. i didn’t not eat all day for him to not see me in my underwear after all date. why do girls spent like 23 dollars on hanky pankys unless they want guys to see them as much as the guys want to.

      • holly golightly on December 4, 2012 at 11:33 pm said:

        oh i’m chill, no worries. so chill i don’t even bother with the undies. i’m just saying i’m quicker to dress down for the real dude, not the boy with all the moves.

  19. I must say, playing “rock, paper, scissors” for the check is a brilliant tactic I will have to use not only on dates, but during client meetings.

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