Dating Your Boss: Women on Reddit Share Their Experiences

Dating Your Boss: Women on Reddit Share Their ExperiencesDating Your Boss: Women on Reddit Share Their Experiences

What could go wrong?

In general, dating your boss is a terrible idea. Sure, things could work out and you could end up happily married down the road, but if things turn sour, your job will be on the line. Four women on Reddit share their experiences dating bosses, with varying degrees of success.

Romantic relationship with boss...

1. ...What now?

romantic relationship with boss

“I work in a small office. Friday was a bad day at work, just one of those days where everything goes wrong so everyone decided to go for drinks after work. We rarely all get together after work so we all drank more than we should have. At the end of the night, everyone was leaving and my boss and I decided to split a cab home since we live in the same area... I'm sure you can see where this is going.

He ended up coming into my house to see my new puppy, we had some more drinks and ended up having sex a few times. I can't say who initiated it, it was probably mutual, but he did say that he's wanted to f*ck me since he hired me. I won't lie, I had thought about it too but obviously never acted on it. He slept over and we had sex again in the morning, but never really talked about it.

So now it's Monday morning and I'm not sure what to do.”

- Fergivicious1

2. Apparently, I was the sidepiece

romantic relationship with boss

“I was the assistant manager, he was the manager. Was amazing for a while and we were a great team, both at work and outside. He was kind of an angry guy though, would get mad at shit like me going up to my best friend’s Halloween party without him (which I invited him to) and I'd get frustrated with him because he only took me on three dates total over the course of 12 months.

Then I found out he had a girlfriend at home.

Ruined friendships with my male friends, ruined my reputation at work, ruined my self-esteem because how stupid am I for staying with him for a whole year? Much regrets.”

- MaeghanKizzia

3. All the regrets

romantic relationship with boss

“I briefly dated my boss's boss. There was an over 30 year age difference. I'd go to his office for ‘meetings’ and we'd just spend it fooling around. I had just gone through a bad break up and I just wanted to be with someone ambitious and dependable (what my ex wasn't). He was nice enough but eventually, the excitement went away.

I began to think of what I was doing and it really started to turn me off. I started getting the feeling that he was manipulating me and taking advantage of me. When I think about it now I'm pretty sure he did it to other women who worked there. It was all consensual but it makes me slightly ill thinking about it.”


4. The happy ending

romantic relationship with boss

“A couple months into working at a new company, I realized I had a crush on my manager. As time went on, my interest just got more and more intense. I did absolutely everything I could to suppress my feelings, but it wasn't very successful when he started showing interest in me, too. One year after I started, we officially became a couple.

For the next year and a half, we kept our relationship tightly hidden. I eventually left the company, and the company eventually went belly up. Still... we kept our relationship hidden from all our old coworkers.

We finally disclosed our relationship when he tried to start a new company with our old coworkers. They were, to say the least, extremely shocked to discover we had managed to keep the secret for so long :)

We're now at 3.5 years and still going strong!”

- Workerdaemon

READ: Are Your Coworkers Secretly Dating? 6 Clues You Should Watch Out For