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?

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