The realities of dating your boss

·7-min read
Photo credit: Roo Lewis
Photo credit: Roo Lewis

Sex with a colleague or boss is a super common sexual fantasy - but it's also a pretty common sexual reality. But what is it like to date your boss? And should you ever enter into a employer-employee relationship with someone who is your manager? How do the power dynamics work, does it get awkward around other colleagues and can you ever find true love at work? These women who dated their bosses share their experiences.

1. "We fell hard and fast for each other"

"I started a new job at a time where the rest of the department was out for training, so it was just him and I. We spent eight hours a day together for two weeks. We ate lunch together in the cafeteria and really got to know each other. We formed a friendship, and we were both aware the other person was single.One night, the department went out for drinks. We both got a little tipsy and because neither of us wanted to drive home, slept at a mutual friend's place and shared the spare bed. Nothing happened, but he did cuddle me throughout the night.

"He struggled with the situation, as he was my supervisor and knew the things could get messy, so he pulled back for a while and we remained friends. After six more weeks, he couldn't stand it anymore and reached out to me outside of work. We started dating soon after and fell hard and fast for each other. We dated for three years. Not together anymore, and during our relationship I ended up taking a job elsewhere, but it was a nice love story at the time." [via]

Photo credit: Roo Lewis
Photo credit: Roo Lewis

2. "It put both of our jobs on the line"

"I was in my early 20s, he was in his 40s. I was waiting tables and he was an assistant manager. We got along well when we worked together, had good banter, kind of a flirtatious teasing relationship. One day when we were talking at work I put my number in his phone and told him to text me if he wanted. He did. It went from there. Honestly, we didn’t really date, just hung out at his place when we got out of work and fooled around, but because of our age difference and because managers weren’t allowed to date servers it put both of our jobs on the line, so we had to keep it quiet." [via]

3. "I got a bit of special treatment"

I had been seeing another waitress casually when she got promoted to being a manager. It honestly didn't change too much but I got a little bit of special treatment. I also couldn't get away with making any excuses to switch shifts or miss a day so I think it balanced out in the end. [via]

4. "Nobody really cared"

"We were only a year apart in age so we started hanging out outside of work. Had a lot of the same friends already, we ourselves were friends for a while before anything really happened. We went on a camping trip, got drunk and slept together. So we started seeing each other after that. Work was pretty much the same. It wasn’t a strict environment, so nobody really cared. It lasted maybe a year. I had a hard time committing fully to her. I wasn’t seeing other people but I also didn’t want to call her my girlfriend. I guess it just wasn’t there for me in some aspects. We’re still really good friends but I wasn’t good for her partner-wise." [via]

Photo credit: Petri Oeschger
Photo credit: Petri Oeschger

5. "We've been together 21 years"

"It was my summer job in college and they brought in a new assistant manager since I had been there the year before. I had just broken up with my college boyfriend of two years and he would not leave me alone. Like, he would drive two hours to my work to see if I was leaving with other guys or just to watch me. My boss would walk me to my car to make sure the ex didn't bother me. Once the ex backed off for several months, my boss asked if I wanted to go to dinner and we've been together 21 years, married 19, and have 2 kids and a dog." [via]

6. "He was at a different stage in life than me"

"I was an intern during my MBA at a Fortune 500 company. I was assigned to work under a relatively younger exec (late 30s/early 40s, I never found out the exact age). We flirted quite a bit during work. He finally made a move on the last day of my internship. He asked me out. We went to a concert that weekend. It was nice, but he was at a different stage in life than me, so it didn't work out." [via]

7. "I no longer work for him"

"We shared a taxi and ended up exchanging numbers. I quit my job when we moved in together... and he hired me because he was tired of me being home. We've been married for 10 years now and I no longer work for him." [via]

Photo credit: Oscar Wong
Photo credit: Oscar Wong

8. "Whenever he was around, I wanted to be near him"

"He was really kind and bent over backwards to make people's lives better/give people opportunities to grow. Whenever he was around, I wanted to be near him. But he was always rushing from one project to another, so we didn't get a lot of time together. Then, at the company Christmas party, he was toasted by the time I showed up with other people. He was hilarious and we had such a fun time. We danced, we drank, we got cut off from the bar. When everyone else went off to the after party, I got his stumbling ass into a cab and then caught up with them. All while he was slurring something about being worried that I get home safe. It started a friendship between us that allowed us to start talking more, and texting in a conversational way instead of a strictly professional way.

After a few months of text-flirting, he took me on a few waterfall adventures and we ended up finally kissing. There was a lot of squealing and jumping when coworkers figured out we were finally together. It's over three years and a lot of life later, we've been separated by COVID borders for 17 months. But he's still my favourite person by a long shot. We've had many talks about rings etc. But ring or not, the day we can finally be in the same country/timezone, I'm dragging that man to a courthouse so we never have to be separated again." [via]

9. "He used work to manipulate me"

"I was 16. He was 28. He used work to manipulate me, make me think my job depended on his 'good will', and was increasingly inappropriate with me over time. I didn't know how to say no while still keeping the job I needed and I wasn't mature enough to know how to shut down his advances properly. After 'dating' for a few months, I broke down and told him I did not want to be with him. I left that job with a healthy 'going away bonus' that the women in the office all gathered up for me and with the knowledge that they all saw it and wanted to help me navigate the issue but were afraid for their own jobs." [via]

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