The Sweet, Awful, and Messy Results of Roommate Hookups

Having a roommate has never been easy. But it's never been harder, either.

With their generational wealth in tatters, their quality of life markedly worse than prior generations, and as they stare down down one of the worst student-debt crises in history, growing up millennial means facing unusual living situations. Many 18- to 34-year-olds are moving back in with their parents, living in "pods," living in boxes inside other apartments, and, more than anything, living with one another at higher rates than ever. More so than their actual, you know, lovers.

But young people, in turn, have upended how they define their closest relationships. We've brought you stories about what happens when students hook up with flatmates—but what about what happens once we've left the bubble of university life? For the Tinder (and perhaps even the Seeking Arrangement) generation, the line between friend and lover has been blurred in unprecedented ways, and the roommate-with-benefits is on the rise. These stories lay out the case for—and against—the awkward, sweet, occasionally life-changing (and more often messy) realities of swapping spit with the same people with whom you split the cable bill.

In the 90s, my roommate AJ and I used to get stoned constantly and be like, "Oh my God, we're stoned, let's fool around." That's how it started.

AJ and I were so close—we had the passwords to each other's bank accounts. And then he stabbed me in the back. He started dating a mutual friend who turned out to be psycho, and she ruined our friendship. She went through my mail and punctured my tires more than once.

AJ was this really great guy at first, until one of his friends said to him, "You're always the nice guy, you'll never get the girl." That's when he really started using me. It hurt. I would not recommend hooking up with your roommate. It gets too messy. In my case, it ruined everything we had. Now I'm happily single.

I was a 19-year-old kid who'd never left Kentucky until I moved to Portland. I was trying to meet people and have a little fun, too. I'd been using [gay hookup app] Scruff to find friends.

I met Chris. Today, he's 51, and I'm 25. When we first hooked up, I wasn't experienced, so we just made out and went slow. At the time, he was partnered to a guy named Lance, and the three of us messed around together. Then they told me, "This home is your home too."

Eventually, Lance left him, and I ended up moving in with Chris. I've been living in his house in a separate room for almost five years. We don't have sex anymore—we stopped three years ago. But we have a lot in common. We both love watching rugby, and I play, too. We're really into hockey; our favorite team is the San Jose Sharks.

I'm transgender and transitioned freshman year of high school. I faced hardcore bullying. My hair was set on fire. I was punched in front of teachers who did nothing. Death threats galore. I needed a safe space, and Chris provided one. Chris just got married less than three months ago, and we're all looking for a house with a basement I can live in. He still wants me in his life. I grew up with a single mother, so he's like the dad I never had.

Today I have a great job, and I'm getting my bachelor's in data analysis. I've been dating, but my tastes have changed. I'm looking for someone my age. I guess as I've grown up things have become less about sex and more about finding someone to share a life with. I hope this doesn't sound ageist, but I'm looking for a peer now. I want someone to grow old with.

All I did while studying abroad in Oxford was read, write, and have sex.

My roommates spent their days drinking pints and eating fish and chips from the store next door. It was me, a girl, and four guys in a three-story flat. We didn't hang out with a lot of British people. It was a dark time.

My roommate Tommy had already slept with another girl in the house, but then he and I started having sex frequently. We would get super wasted and end up having the best sex I'd ever had. I ended up going to a polo match with Tommy outside London. We were all dressed up, and it was really fun. But then we got wasted, and I got escorted out of the polo match.

Doing it doggy style in a house with five other roommates was pretty fun. It also felt really raunchy because we were sneaking around. I've only seen him once since. He came to stay with me, and we had sex one more time, then I blocked him on everything. Now I have a male roommate, and we're like brothers. But I will never, ever sleep with a roommate again. It just gets so weird so fast. And then it makes everyone else in the apartment feel weird. I'm over it.

I live in Denver and work in the travel industry. I've typically lived alone, but last year, I had a roommate for six months that I met on Grindr. We initially met for a hookup, and I wanted to date, but he wasn't interested. He needed a room, though, so I leased one to him for $400 a month. Once he moved in, we agreed the fooling around had to end.

He was from Pakistan, and he cooked delicious meals almost every day, which was certainly nice for me. After dinner, I would make us a pot of English tea, and we'd watch his Pakistani soap operas on YouTube. I couldn't understand a word, but I knew exactly what was going on. Then I would give him a foot massage, and he'd be off to bed. In some ways, we were like a married couple, without the sex. It was a sweet, nice relationship, but without sexual tension or any stress.

On the whole, I really enjoyed it, and I miss him today. Once he moved away, I went back to living alone. It was one of those rare, special experiences that occasionally come along in life. I gained a lovely friend—we still stay in touch and have warm memories of our time together.

On dating apps, it's really unlikely you'll find anyone reliable or dependable, someone you can really count on. But sometimes you'll meet someone special. So don't dismiss everyone.

I'm a bartender and live in Bushwick, Brooklyn. You can call me a hipster if you want, but I eschew the term. I do play keyboards and bass in two bands, though.

I lived in this DIY, punk-house kinda place for a year. It was rat-infested. A lot of DIY spaces in Bushwick have live-in lofts, like tiny cubbies. And that's where I met Nate. There were a lot of us living there. Nate and I were friends for many years, but never hooked up.

One night, very, very drunk, we left the main stage after a show and went to his bedroom, which was particularly vulnerable to rats because it was next to the kitchen. We were having sex right as the rats were coming out, and he has a rat phobia. He fuckin' lost his shit. Ran out the door with his pants around his ankles. And we never hooked up again.

Follow Conor Bezane on Twitter or his blog.