10 Horrifying Stories Of Workplace Romance

Although there are plenty of no-brainer duh reasons why you shouldn’t get romantically involved with a coworker, office hook-ups are laughably inevitable. For one, spending at least 40 hours a week with people begets very close relationships — many that ascend to intimacy. Others who fall victim to work romances develop affinities for nurturing bosses and mentors in powerful positions, confusing admiration for a crush. Then, there are the folks who simply want to engage in fun trysts, given the convenience of the situation.

While some companies have guidelines against in-office romances, following the rules can be impossible, especially when the sexual tension is too much to ignore. And to be fair, it’s not all bad — according to a 2011 Career Builder study, about 30% of all workplace romances lead to marriage. But for every success story, there are many more that end in regret. Ahead, we rounded up 10 true tales of workplace romances that might have you thinking twice before you proposition your office crush this Valentine’s Day.
1 of 10
Illustrated by Mallory Heyer.
Once I went to drinks and karaoke with a guy I worked with. After 9,000 drinks we made out, much to my surprise. We were polar opposites — he was INCREDIBLY preppy. I am talking whales on a belt.

The next morning, I woke up in his bed with an incredible hangover, and he was already dressed in a polo shirt and crewneck cashmere sweater. He was practicing his golf skills on a fake putting green in his bedroom. I was still in my clothes from the night before and had no way to get home to change before work (I lived 30 miles away). He suggested I call in sick, but I had the most important interview of my journalism career that day.

We drove to a coworker’s apartment so I could borrow a dress, even though she is 5-foot-10 and I am 5 feet tall. The coworker didn't even offer me the chance to shower, and I reeked of alcohol, cigarettes, and 22-year-old reckless abandon. So before I headed into the office, I went to a local Rite-Aid and bought a size XXL T-shirt. I pretended to check out the shower facilities at a local Gold's Gym so I could shower and use the T-shirt as a towel. I put on the oversized dress and somehow made it to my interview on time.

I hung out with J. Crew dude a couple of more times, just because I think I was his version of slumming it. Plus, his apartment was close to our office.
2 of 10
Illustrated by Mallory Heyer.
He was my boss at my first job out of college, and I admired and respected him, but I also thought of him as a very good friend. That's probably how everyone at the company thought of him. Some of his advances were sketchy, some were kind of romantic, but overall he was very persistent, and eventually I threw caution to the wind, and we started to quietly date.

But after a while, he told me I wasn't the only woman in the office that he was dating. I assumed the other girl (my coworker and friend) found out about me and forced him to come clean. I was completely shocked, just flabbergasted. I had no idea there was anything between them. I felt really hurt and betrayed, angry, disgusted, and also ashamed that I was in a scenario I never would have thought to be in. Life is too short to work for an asshole! I really didn't see any other choice but to quit — it was my first job out of college.

I didn’t know how to handle the situation, so my roommate’s mom put me in touch with a sexual discrimination lawyer. The lawyer advised me on the language I should use in my resignation letter and the sum I should ask for as a compensation for essentially leaving quietly. So, in addition to being an emotional wreck, I also had to try to compose myself enough to come across as genuinely litigious and not be scared shitless about the consequences. Looking back, I still can’t believe I did that. But I guess this shit happens every day.

Fortunately, the lawyer’s advice worked, and I was compensated, which made me feel gross initially, but in the long run was SO CRUCIAL because it took me a while to find a new job. I mean, I was too scared to even ask for references, since that had been my only real job! It was a terrible life lesson that could have been avoided if I didn’t get involved with someone at work, much less my boss — god knows I mentally turned back the clock a million times. But of course I thought my situation was different, as we all do, so this may have been the only way for me learn that lesson.
3 of 10
Illustrated by Mallory Heyer.
I never thought I’d be the “older woman” in a relationship, but when I was 30, I fell for my male intern who at the time was a 21-year-old senior in college. I couldn’t help it — he was really cool for someone his age! Much cooler than the losers my own age. I knew it was shady of me, but I started inviting my intern to hang out, first to grab lunch or coffee, and then to after-work drinks. I tried my best to keep things professional, but I might have let things get a bit too flirty between us.

One particularly drunken night after a happy hour, my intern offered to walk me home. When we got to my stoop, he boldly asked if he could kiss me. It was so hot. But of course the next morning I was a crazy person about the whole thing. He said our relationship was important to him, so he ended up dropping out of the internship program so we could date.

Outside of the office, I literally felt like I was dating a kid, especially when I went to his college campus to hang out with him. I ended things like a month later. The worst part for him was that he had to stay an extra semester to find another internship to fulfill the college credits he couldn’t get from my company. It turns out he has a thing for older women — I hear he fell in love with the VP of his department at his first job out of school, and they have a child now.
4 of 10
Illustrated by Mallory Heyer.
Sam and I had kitty-corner cubicles. We would share Rhapsody playlists, halal cart food, and loving (and unrequited) stares during long boring meetings. He had a girlfriend who was still in college and she would send him funny illustrations that he would post on his cubicle walls. They made me so jealous. But Sam and I continued to be friends. We went to concerts together after work and to the bookstore during lunch breaks.

Many moons later he told me he and his girlfriend broke up. I invited him over to my apartment. I should have been excited, but everything felt out of sync. We watched Love, Actually, which was actually terrible. Then we had sex, but I felt empty afterwards. The moment I knew it wasn’t meant to be was when he picked up my guitar. It was a major turn off. He didn’t even know how to play.

After that moment I literally stopped speaking to him just because it was so awkward! There had been so much sexual tension between us, but once we hooked up, it all felt meaningless. Eventually, we had a mature conversation about the whole thing, but a few weeks later he got a new job. I heard he took a $6,000 pay cut.
5 of 10
Illustrated by Mallory Heyer.
It didn’t happen to me personally, but at my first job out of college, there were two people in a small office who were having an open affair as far as everyone in the office was concerned. Just about every day at lunch, they went in the woman's office — which was right next to my cube — and shut the door and drew the curtains, Mad Men-style, for at least an hour. I was so young and naive that I had no idea what they were doing behind that door. Everyone else knew what was up, but no one acknowledged it. At the time, they were married to other people, but I later heard from an old coworker that the two lovebirds ended up getting together eventually!
6 of 10
Illustrated by Mallory Heyer.
I started dating this guy who worked in a different department, and we made a big deal of keeping it a secret even though I think everybody knew what was going on. He would often complain that his boss was unfairly mean to him, but I only knew his side of the story, so I figured it was true. I helped him get transferred to a better job in my department. I thought I'd done this great thing.

Shortly thereafter we broke up, which was timed perfectly because I just started a new job somewhere else. But for months afterwards, I would hear from my old coworkers that he was terrible at the new job and no one liked him. I felt bad that I'd helped him get the job, inflicted his awful work ethic on my former colleagues, and then bounced.
7 of 10
Illustrated by Mallory Heyer.
I once made out with a (much senior) coworker after a drunken happy hour when I was 23 or 24. He ignored me for the next three days after the incident, and I learned that right after we made out, he had ended his relationship of four years. I was confused and sort of stunned that he may have broken up with his live-in girlfriend because of me.

We dated secretly for a few months after that. It was strange and strained. Eventually everyone found out, and it was awkward with our coworkers. Then things got really uncomfortable. Regrettably, I think it painted me a in a certain light to the executive-level staff. He ended up leaving the company and shutting down his entire division in the wake. I stayed on for a few more years, but that relationship has always followed me.
8 of 10
Illustrated by Mallory Heyer.
Working on film productions feels a lot like being at summer camp — you’re with the same crew every day for months, for 14 hours a day. You can cut through all the sexual tension in the air with a knife.

I was on a job a few years back, and there was a gorgeous craft service guy. He looked like a model — Ryan Phillippe-meets-Brad Pitt good-looking. All the girls would flirt with him, and he was really friendly back, so everyone thought they had a chance. We got drunk and flirty one night, and he ended up inviting me back to his place. Once we got there, he got really serious and said all this cheesy stuff about how he thought we had a deep connection and shit. But I basically just wanted to get laid.

When I got his pants off I was mortified to find out that he had an STI situation going down there. When he saw how freaked out I looked, he said he had been wearing jeans that were too tight. Yeah. Okay, dude. I knew I couldn’t have sex with him anymore. Plus, I felt it was my civil duty as a woman to warn the other girls. I felt half bad about outing him.

After that night we never hung out again, and all the girls stopped flirting with him.
9 of 10
Illustrated by Mallory Heyer.
Matt and I had discreetly started dating in the office and we tried to keep things on the DL. We’d exchange super long email threads of steamy messages back and forth all day. In one of our emails, I asked Matt if he had our old boss’ email address (he had left the company a couple of months prior). But Matt accidentally cc'ed our old boss to our email thread instead! I was super mortified. Our old boss seemed pretty amused by it though, replying to both of us that he had always suspected something was going on.
10 of 10
Illustrated by Mallory Heyer.
I was interning at a small record label with only four employees. At any given moment, you could be working with one other person for the entire day. On one of those days when everyone else was out, I had sex with an employee in the office. We were going at it doggy style and afterwards he told me that the condom ripped and he had finished inside of me. I had to get Plan B.

I was dating a different guy a little more seriously at the time, so I lied and said I might have gotten pregnant by him. I made him come with me to get the pill and had him pay for it.

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