Casual Dating For Defeatists: A Survival Guide

One of the most frustrating things (so far) about my unmoored twenties is that I’m incapable of comprehending anything. I find myself needing to learn and re-learn the same lessons; nothing seems to stick. I know, for example, that going to the gym will make me feel great and is occasionally the only part of my day that gives me any sense of forward momentum, but convincing myself to go is still a chore. Every time I go, I learn this lesson anew, only to forget it the following evening. And calisthenics are not the only area of my life in which this lack of retention has surfaced.

Perhaps the strangest occurrence of the past six months or so is that I’ve had my first sustained brush with dating. I don’t know what it is, but the combination of desperation/ anxiety /immaturity must be some kind of pheromone for gay men. On this seemingly endless string of first dates, I’ve picked up a few ideas about dating (only to forget them 48 hours later). So, without further ado, I offer you the Quarter-Lifer Who’s Never Really Done Much Dating but Now Finds Himself Thrown into the Romantic Deep-End’s Guide to Dating, for the Neurotic Self-Saboteur in All of Us:

[A legal disclaimer: There is no one on the planet less qualified to talk about dating in any sort of successful way. These simple tenets were generated by a string of humorously unsuccessful first dates (with a few successful ones thrown in the mix; even a stopped clock is right twice a day). I can guarantee, however, that these thoughts will enrich your post-date Last Five Years sing-along, which is the cornerstone to any successful self-medication attempt.]

There’s always more: Seriously, look around you. All the most obnoxious people you know are dating someone, sometimes multiple someones. Even if the date is going really well, there will be more awkward first dates in your future. When the person sitting across the table from you decides to stop answering your calls, there will always be another painfully attractive asshole waiting in the wings to repeat the experience. You will go on other dates. And they will suck just as hard as this one does.

Sometimes it really isn’t your fault: That really cute guy sitting across the table has stopped answering your text messages. And you’re sure, neurotic as you are, that it’s because you accidentally mentioned the time when you celebrated Tyra Bank’s birthday (December 4th, incidentally) by wearing a yellow sundress and having a photo shoot/ walk-off. Or else you showed up to dinner wearing the same shirt you’ve been wearing for four consecutive days. Without trying to sound like a deluded 17-year-old prom queen, sometimes it isn’t something you said. Really. Either bad timing, lack of chemistry, or a weird head shape can mean that you’ve done everything right and still aren’t getting a callback.

Sometimes it really is your fault: You accidentally made a joke about wearing his skin as a suit (we’ve all made that mistake once or twice), you got drunk and vomited on him, or you made some comment about transnational sexualities that he 115% misunderstood. In any case, this date went sour as a direct result of something you did. Well, the joke’s on him, because you are going to screw it up over and over and over again for the rest of your life. Two years into a relationship, you are going to continue to say exactly the wrong thing. I might even argue that interpersonal relationships are about failure above anything else. If that’s the dealbreaker, screw ’em. As someone whose foot likes to live in his mouth, I repeat: screw ’em. There’s only so much apologizing (or accommodating) you can do for your inept mode of communication.

Don’t be intimidated by other people: Admittedly, this is the lesson on this desperation checklist with which I am most uncomfortable. That 6’2”, blond, crazy attractive former-athlete you suddenly find yourself sitting across the table from (God only knows how)? He’s a person, and probably a less interesting person than you are. Glitter/ sunshine doesn’t fall out of any of his orifices and 7-9 times out of 10 (depending on how attractive/ what a basket-case you are), he’s every bit as jittery as you are and just as likely to say something stupid. No one escapes the horror of dating. No one has an upper hand. This dinner is about to suck for both of you.

Hide the crazy: In the car, on the way to this date, you listened to the Rocky theme four times, followed immediately by “The Greatest Love of All,” “And I’m Telling You (I’m Not Going)”, “Shake It Out,” “All I Really Want,” and any number of determination anthems that occurred to you. You even showed up 45 minutes early so you could accomplish this sadness sing-along and still be on time. Whatever you do, do not mention this. As an Ally Sheedy-sized nut job, I can tell you that no good will come of it. You might think it’s quirky and endearing, especially if you’ve just finished a lengthy conversation about Liz Lemon, and maybe one day it will be. For now though, nothing cuts a date short like tipping the hand of your neuroses. Hold it in, even if that means you cry all the way home because you’re pretty sure there’s no cat heaven.

Don’t over-think it: There’s so much crap circulating about the right and wrong ways to approach dating (the previous paragraphs included). Wait three days to call, make sure they don’t think you like them too much, retain some air of mystery, be as oblique as possible, etc. My general feeling is, messy and complicated as people are, dating them can be surprisingly simple. If they like you, you’ve got a lot of leeway in terms of approaching them. (When’s the last time you were put off because someone you really liked was texting you too frequently?) If they don’t like you, it really doesn’t matter how long you wait to respond to their message, does it? Despite the terrifying minutia dating induces, isn’t it ultimately governed by a relatively simple bottom line? They either like you or they don’t. You either like them or you don’t. I think we can probably all benefit from being told not to worry so goddamn much, right? TC mark

image – Shutterstock


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  • Glenn Kisela

    Hide the crazy. For some people, it means wearing shades, because you have it so much your eyes are giving you away.

    • Asdf

      The crazy eyes, aka the Gary Busey eyes, aka the Michele Bachmann eyes. The eyes give it all away.

  • ollinomates

    Amazing :) 

  • Charlene

    I needed this. Thank you!

  • angel


  • Weslee Janisen

    I’m obsessed with you. This was everything I believe and some things I didn’t even KNOW I believed until you made me believe them! Good luck out there on the dating battlefield, dude. We’re all right there in the trenches with you! 

  • ach

    This is great!

  • Grace

    LOVED this.

  • Holly

    As someone who can totally relate to this (and has gotten some insight after seeing a therapist), if you have issues with yourself (i.e. think there’s something wrong with you, don’t think you’re ‘enough,’ didn’t feel loved), it will come back to bite you in the ass later. The best thing to do is to be comfortable with yourself– flaws and all. Get out of the habit of judging yourself so harshly. I know, it’s easier said than done. But totally possible.

    • Holly

      Also, losing the notion of ‘the one’ or someone making you happy or rescuing you/make your problems go away helps a lot too.

  • Lassyvious

    Looove the article, but it’s tenets, not tenants*

  • Yasmita143

    First time making a comment on TC. Felt like I had to because I loved this article so much! Thank you for sharing this. Very much appreciated :)

  • Bridget

    I can’t believe Tyra’s birthday has been immortalized on an Internet publication in an article on dating. So, so proud.

  • Bridget

    I can’t believe Tyra’s birthday has been immortalized on an Internet publication in an article on dating. So, so proud.

  • Bwoodbury

    I can’t believe Tyra’s birthday has been immortalized on an Internet publication in an article on dating. So, so proud.

    • Josh

      I think we got the point. You’re happy. Yay you.

  • DCustreet

    Can we go on a date?

  • Tiffany

    My favorite was “Hide the Crazy” .. the whole Rocky theme song playing in the car before the first date. Hahaha!

  • Sophia Anderson

    This is one of my favorite things I’ve read on TC in a while, and not just because of the Last Five years shout-out. Well done, I totally identify with your particular brand of crazy.

  • Hannah Amante

    The Last Five Years! :) 

  • Chairman Meow

    What do you mean there’s no cat heaven? You asshole.

  • AJ

    My birthday is December 4th, we should celebrate that sometime. Also, good work.

  • J in DC

    Great article.  I am generally okay with the whole wearing the yellow sun dress to celebrate Tyra’s birthday.  BUT, to wear that in December …. now, that’s crazy

  • tati

    this totally put a smile on my face.

  • JP

    God bless your soul

  • Shawn

    The biggest tip of all;

    Just have fun. I mean, what’s the harm? If it doesn’t work out, you had a good dinner/drink/roll-around-the-hay. If it does… then you know that person you can have fun with. And that’s 75% of a potential relationship.

    I’ve learned that when people try to “play it cool”, they just come off as disinterested or stuck up. Smiling is 50% of the battle. Really.

  • jejune

    it took me until just now to realize that Thought Catalog is just cosmopolitan for bookish 20-somethings!

    good article, i’d totally celebrate tyra’s birthday w/ u!

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