Sex + Dating

All of Your Terrible Ex-Boyfriends, Ranked

bad ex boyfriends
Daniel Fishel/Thrillist

Remember that terrible guy you dated in college/post-college/last year?

The guy who cheated on you with your roommate? The weed dealer you went out with because you knew you'd get free pot? The guy who gave literally zero F's about you, but you loved anyway? Yeah. That guy.

We've all got a few terrible ex-boyfriends. But how to decide which was the absolute worst? Rest easy: I've saved you the trouble by ranking all of your exes in order of suckiness. You're welcome.

14. The Cheater

He's the dude who slept with your college roommate while you were out with your friends. He constantly liked random models' Instagram photos and sent them DMs… only to get rejected because he was gross. And yet you stayed with him. God, he was the worst.

What he’s doing now: As the old saying goes, "Once a cheater, always a cheater." He married some poor girl and is currently screwing his secretary.

The bright side: You didn't end up with this horrible excuse for a person.

13. The F**kboy

This guy is somehow simultaneously narcissistic and incredibly insecure. The sad part is, he had no idea how transparent his insecurities and selfishness were while you were with him. He told you he really liked you, only to fall off the face of the Earth and never be heard from again. He did want you to know that he wasn't looking for anything serious, but was down to hook up." *pukes*

What he’s doing now: He’s hanging out at the local dive bar, hitting on 21-year-olds, and regaling anyone who will listen with stories of his frat days. His clothes are a bit too tight since homeboy has put on some weight and refuses to acknowledge it. He's come to discover a new feeling lately: It's called REJECTION.

The bright side: There is nothing attractive about a pseudo-intellectual with a God complex and beer belly.

12. The "Nice" Guy

Newsflash: Any guy who says he's a nice guy IS NOT A NICE GUY. He took you to dinner, paid for everything, and said all the right things. He wanted you to know he's a "really good guy" and "isn't like the other guys you've dated." He did this to lull you into a false sense of security so he could have sex with you.

After a string of perfect dates, he introduced you to his parents. You thought, "Wow. This could be it." On the way home, he took your hand, looked deeply into your eyes, and said, "You know we're not dating, right? You're not my girlfriend. I'm not looking to have a girlfriend right now."

Bastard.

Where he is now: He tells his friends and family that he "just wants to find a great girl and settle down," but he continuously takes out great girls, lets them know he's a "really nice guy," and then totally chickens out of making any real commitment.

The bright side: The next time some assclown tells you he's a "nice guy,” you now know to RUN in the other direction.

11. The Weed Dealer

The Weed Dealer is the staple of every college girl's dating experience. Right? Right??

He wore a drug rug, probably had dreadlocks, and was always in a super-chill mood. He wasn't exactly attractive; but you needed weed, he was around, and was always super-nice to you.

After mimicking the plot of Dazed and Confused for several months, you realized this guy's lack of aspirations and all his illegal activity did not exactly make him husband material. So, you sent him on his merry way, no hard feelings.

Where he is now: He's pursuing a master's degree in philosophy, contemplating the universe's vastness. He's recently started mixing electronic music and his EP is "coming out soon."

The bright side: He was never going to be the love of your life, just the love of your high, maaaan.

10. The Bad Boy

The Bad Boy: the Achilles heel of every girl in her teens and 20s. UGH. He was so irresistible. He drove a motorcycle, had a few inexplicable tattoos, and your parents hated him. DREAMBOAT.

After one-too-many shots and a few too many heartaches, you had to let this guy go. He only had dreams of metal concerts and traveling the open road, and you had bigger plans than that.

Where he is now: He dropped out of college his senior year because he couldn't take the yuppies. He's massively in debt, with no degree to show for it. He's working as an auto mechanic and chopping wood for the cabin he squats in upstate.

The bright side: All former Bad Boys become old men with beer bellies, nostalgic for the glory days. It is not cute anymore.

9. The Softboy

The Softboy is into his emotions. He wants you to know that he is super-into his emotions. He'd like you to be down for his emotions. He loves his art and he loves his music. He can't deal with the prospect of giving up his art or his music. He lives for it, OK?

He will stop texting you for days at a time because he's just so wrapped up in some incredible, not-at-all stupid, creative endeavor. He's super-sorry, he's just so involved in making art. He likes you, but he can't be a good boyfriend because his painting/drawing/filmmaking/music is his true mistress.

Where he is now: He moved back home after realizing his film degree was worthless in the city and he was massively under-qualified for a real job. He's still in a band and has high hopes that they're really going to make it big.

The bright side: He's a Softboy and he is a toolbag. And you are no longer dating him.

8. The Way-Too-Old-for-You Guy

After dating a bunch of immature morons, it was easy to think dating a guy 15 years your senior was a great idea. He was so worldly! So wise! The thing you forgot? Any 35-year-old man who wants to date a 20-year-old girl is not a mentally healthy person.

He may have been rich, but there was clearly something wrong with this guy. He dated you because he wanted to feel young and have a hot POA on his arm. He wasn't really into you for your personality. He just wanted to regain his youth by dating a woman half his age to cover up blatant insecurities.

Where is now: He is still dating 20-something women and will continue to do so well into his 60s. He will be a forever bachelor, choking down the Viagra and always in search of greener pastures despite his wrinkly balls and butt cheeks.

The bright side: You learn that dating men way older than you says a lot more about them than it does about you.

7. The Aspiring Actor

He is always going to auditions between his hefty schedule of waiting tables. He's an actor first and a waiter second. It's only his day job!

Never mind that he played Rosencrantz and not Hamlet in his college production of Hamlet. He KNOWS he's the most talented actor out there. Sure, his college wasn't even known for theater, but that's not going to deter him. He's going to star in big blockbuster hits and show Mr. Hardy, his acting teacher, that he was wrong about him!

What he’s doing now: He's still a waiter. Duh. He did recently play a dead body on an episode of SVU, so that's something, I guess.

The bright side: You're not dating a waiter anymore.

6. The Party Boy With a Drinking Problem

He was the life of the party, downed shots like it was his job, and usually ended up in a fight. After college, he just kept on going out like he was 23.

This dude walked the line between being a guy who liked to have a good time and a full-blown alcoholic. At some point, you realized the party would never be over for him -- and that it was definitely, most certainly over for you.

Where he is now: He got fired from his finance job after blacking out at the holiday party, screaming that white men are the most disenfranchised group in America, and passing out in a corner. He's looking for a new job, if you know anyone who's hiring.

The bright side: You were getting pretty close to cultivating a drinking problem yourself and didn't end up going that far. Snaps for you!

5. The Genius Loser

He was so insanely smart that it blew you away. You were dazzled by his astute observations about mankind and the seemingly endless flow of information he had about pretty much any subject.

He was also the laziest person you'd ever met. He couldn't cope with the tediousness of hard work in such a basic world. He didn't have a job and really wasn't going much of anywhere because he couldn't get it together. For someone so smart, he was actually really dumb… and had a nasty sense of entitlement.

Where he is now: He's still spending most of his time online, arguing politics with internet trolls and reading massive 19th-century volumes. If only you could get paid to be a pretentious prick.

The bright side: After all this time, you now realize YOU are intellectually superior to HIM because you are not still living in your parents' house, broke and unshowered, talking to strangers in internet chatrooms.

4. The Mama's Boy

They say to date a man who loves his mother, right? If only he liked you as much as he liked his mom. Seriously, it was weird how much this kid loved his mom.

He was a nice and all, but how did he have time to call his mother four times a day? He couldn't do anything without his mother's approval -- including buying underwear without calling her to check the brand. Meanwhile, she never thought you were good enough for him. She hated you. The whole relationship was doomed from the start.

Where he is now: He's married to a woman exactly like his mother.

The bright side: You do not have to spend the rest of your life in the company of his mother.

3. The "Good on Paper” Guy

He checked every single one of your boxes. He was smart, cute, and had a great career. He was nice to his sisters, loved children, and was looking to settle down. If only there had been a spark. God, you would have KILLED for a spark.

You tried to force it. You even made sexy noises during intercourse despite the boring sex you two had. But something just felt off; and you eventually broke it off.

Where he is now: He found a nice girl who thinks dating him is like being with a fudge caramel sundae with whipped cream.

The bright side: You now know you can't force love. It's an important lesson... even if it sucks.

2. The Entrepreneur

Startups are so hot right now. Anyone who's anyone has a startup, didn't you know? Your ex's startup sounded alarmingly like Yelp, but you didn't want to hurt his feelings. His passion was sexy; but he was always working. He even checked his phone once during a blow job.

You spent so many nights on your own or third-wheeling with your couple friends, things got depressing fast. It wasn't like he was going to give up his startup for you.

Where he is now: His startup totally flopped, probably.

The bright side: His startup idea sucked anyway.

1. The One Who Got Away

We've all got that one ex who was actually super-great and we were just too young and stupid to realize it. After dating all of the aforementioned assholes, sometimes you look back on a particular ex and think, "Shit. That dude was the BEST and I messed up." He brought you coffee in bed, always thought of your feelings, and asked how your mom was doing. So, of course you decided to completely screw it up. Nice one!

What he’s doing now: He probably found another (though super-basic, I'm sure) girlfriend who was ready to settle down and be a wife. He's probably got a golden retriever and wears dad jeans from Levi's.

The bright side: If he was really the love of your life, he wouldn't be the one who got away. Now that you have a complete list of utter dickwads on your dating roster, you can go out and find someone who really is the coolest. Happy hunting!

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Gigi Engle is Thrillist's Sex and Dating staff writer. Writing this was easy, considering she's dated every one of these dickwads. #SLUTLIFE. Follow her lovable crazy on Twitter, iTunesFacebook, and Instagram @GigiEngle.