The 10 Terrible People You Date in Your 20s

Ryan O’Connell


If you’re in your twenties, chances are you have dated one (or all) of these terrible people:

THE THIRTY-FIVE-YEAR-OLD MAN-CHILD WITH A HUGE DICK

The man-child is typically very attractive and wears lots of flannel and age-inappropriate footwear. You would never guess he’s thirty-five (and newly divorced from a fellow artist type named Ursula), but the bags under his eyes ultimately give him away. A man-child has to date a decade (or two) younger because any girl in his age group would run away screaming. Certain girls love to date him, though, because they claim to be attracted to men who are creative. The real reasons, however, stem from a deep-seated desire to piss off their well-to-do parents and have as much amazing sex as humanly possible. That’s the one good thing about dating a man-child — they’re fantastic lays and their dicks are humongous, which makes sense because only someone with a Dirk Diggler shlong can get away with acting so immature and helpless. Remember: a big penis doesn’t pay the rent. Usually.

THE PERSON YOU ACCIDENTALLY DATE FOR FOUR MONTHS BECAUSE IT WAS COLD OUT

Have you ever found yourself feeling totally bored and accidentally dating a dud . . . for four months? You’re not quite sure how it happened — you were only supposed to hook up a few times — but here you are cuddling and watching the snow fall from your window together. You wonder, “How did this happen? Was I really too lazy to buy a new winter coat this year so I used a human body instead?” The answer is yes, you bum. You can only casually date a person for so long. There comes a point where you have to either make it exclusive or get rid of them entirely. In my experience, the four-month mark is usually when you decide if you want to transition into spring with this person.

THE PSYCHO BITCH

The psycho bitch is sort of like Glenn Close’s character in Fatal Attraction but infinitely worse because he or she is able to send you text messages. Dating someone who’s unstable is not only a headache; it’s a total amateur move. People usually get them out of the way in their first or second relationship. It’s better to experience the highs and lows early on when you don’t know who you are or what you want and you actually have the energy to fight. I can’t imagine dating a psycho bitch now. I don’t even have the stamina to put on my psoriasis medication, let alone validate someone’s feelings every five seconds.

THE STONER

It’s practically mandated by God that, at some point in our lives, we spend time sitting in someone’s crappy apartment and watching them do bong rips while watching Family Guy. How do stoners get laid so often? They’re so lazy and weird, and yet somehow, they’re always swimming in sex. I don’t get it. Do I need to talk more about the bizarre shape of a Cheeto in order to have sex with someone?

THE PERSON YOU DATE IN COLLEGE WHO RUINS YOU FOREVER

Having a relationship in college is like living in a dream-world. You spend every waking moment together and seriously entertain the idea of moving in together. It feels like this could be the one, but — oops! — it’s not. After you graduate, the relationship fails to translate to real life, and you’re stuck with someone who feels like a soggy appetizer that’s meant to tide you over until the main entrée. Eventually you break up and spend the better part of your twenties getting over it.

THE PERSON YOU’RE ASHAMED TO BE DATING SO YOU DOWNPLAY THE RELATIONSHIP TO YOUR FRIENDS AND HOPE NO ONE FINDS OUT

“He’s just a friend! We’re not dating! I would never date him. I mean, are you kidding me?” Cut to ten minutes later when your friends leave and you call the Shame Crush and tell him to come over and bring pita chips. Everyone sleeps with someone they’re hesitant to bring around their friends. The best thing you can do when you’re sleeping with someone you’re ashamed of is to be honest and tell your friends, “Listen, guys. I’m sort of with this dude, but it will be over when my depression and/or boredom lifts. Just stand by until I feel normal enough to dump him.”

THE NICE GUY

I’m not talking about the type of person who is kind and genuine. I’m talking about a guy who has no discernible quality other than being nice. He’s a bland scoop of vanilla ice cream and you are the sun that is melting him down to mush. Nice guys will turn you into a person who’s mean, a person who’s a bully, a person who points out the flaws, because there needs to be somebody in the relationship who isn’t loving blindly. Nice guys don’t look at you through a critical lens; they love deeply and stupidly, like you’re a puppy and they’re just looking for a man’s best friend. You could be anyone, really. They don’t care. They just want to love something. And they like it when you push them down. They need that. When I date a nice guy, it always ends the same way. I hate them for being so pure, and then I hate myself for being so dirty.

YOUR EX

I know what you did last summer and the summer before that. It was your ex — the person whom you still text when you’re drunk at 4:00 a.m., being like, “Beb? R u there? Just missing you. Cum over if u want. No pressure. I’m so wasted . . .” It’s important to let them know you’re wasted so they know you’re not in your right mind. Then you wait for their response, which will either be, “Okay, be right there!” or “WTF? Um, no . . .” If you’re “lucky” and get the former response, you’re setting yourself up for sex that can continue for a shockingly long time. Sometimes it won’t stop until you get into a new relationship, proving that in order to get over certain people, you need to get under someone else.

THE EMOTIONALLY CLOSED-OFF ASSHOLE

If you haven’t been the asshole in the relationship, chances are you’ve dated the asshole. There are so many terrible things about dating someone who’s emotionally distant and puts you down in subtle, creepy ways, but perhaps the worst thing is that you honestly believe you can change them. It can take years/forever (#dark) for you to realize that it’s just not in the asshole’s DNA to be sweet. Those rare moments of tenderness they show you are just tricks to keep you around longer. You’ll never be good enough. They hate your friends, the clothes you wear, and the things you choose to talk about. But most of all, they just hate themselves.

THE PERSON YOU DIDN’T REALIZE YOU WERE ACTUALLY DATING

Since we’re all a bunch of commitment-phobes, we often end up in the gray area with the people we date, which is a terrible place to be for everyone! If you’re the person who’s getting sent mixed signals, you’re resigned to being an insecure wreck until you’re given some definitive answers. You’re clutching your phone like it’s a lifeline and going into full-body spasms whenever you get a new text message. If you’re in a position of power and keeping things loose and vague, it can still suck because you risk having someone think you’re actually together when you’re simply dating. Before you know it, you’ll be getting an “in a relationship” request from someone you can’t even bring yourself to text back in a timely manner.


Ryan is a writer for MTV’s Awkward and also wrote a book called I’m Special, which you can buy tomorrow, June 2. He likes watching YouTube videos of Mary-Kate Olsen trying to speak.


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From I’M SPECIAL by Ryan O’Connell. Copyright © 2015 by Ryan O’Connell. Reprinted by permission of Simon & Schuster, Inc. All rights reserved.