Confession: I Secretly Dated My Boss

I Secretly Dated My Boss

Okay, so maybe it wasn't quite like this...


I’ll never forget the first day I met K. I was 18-years-old, I had just started hostessing at a local restaurant, and I wasn’t exactly fitting in. My co-workers were a loud-mouthed, super outgoing group of people, and, well, let’s just say I won Most Shyin high school. K and I were standing on opposite sides of the salad window (very romantic, I know), and he asked me what my name was. When I answered quietly, he told me not to be so shy, winked at me, and handed me a bowl of croutons.

At first, I had no interest in K. I was in a slowly failing 5-year relationship with my high school sweetheart and had no interest in being with anyone else. K had a girlfriend, he was 10 years older than me, and, oh yeah… he was also one of my managers. None of these facts kept him from flirting with me, and I started to flirt back a little, too.

If only our restaurant makeout sessions were this romantic...

It didn’t take that long before our innocent flirting escalated to a daily basis. I picked up extra shifts when I knew he was working, and he started scheduling me to work later when he was closing the restaurant. I broke up with my boyfriend, and he started fighting with his girlfriend. The day one of my co-workers pulled me aside to ask, ‘Is there anything going on with you and K?’, I almost choked on my french fry. I liked my job, and he liked his. If anything more happened between us, and someone found out, we could be fired.

One night, K asked me to come back to the restaurant when it was closed to ‘talk’. We kissed in the office, and from there, things only got worse. K and I started sneaking around on a regular basis. Our favorite hang out spots? The storage closet and the office in the restaurant, his car or my car in a random parking lot, and sometimes even the walk-in refrigerator. Not so romantic, I know, and I felt super guilty since he still had a girlfriend–but it seemed exciting at the time.

My first (and only!) secret affair

It was fun until it wasn’t anymore. Rumors spread through the restaurant so fast my head was spinning, and soon we both spent more time denying our relationship than actually talking to each other. Our once-fun hang out sessions turned into long arguments with me trying to convince him he wasn’t going to lose his job. It was a disaster, and it got even worse when the other managers heard the rumors.

Things with me and K never ended up working out – shocking, I know. I was devastated when it ended, and it took me a while to realize how bad he was for me. But even though everything that I did with K hurt my reputation and made me feel extremely guilty, I don’t regret it. I learned a lot of important lessons from being with him. Number one? Stay away from my future bosses.


Posted in: Discuss, Health, Sex & Relationships, Hooking Up, Hookup Confessions, Love&Sex, Relationships
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1 Comment

  1. avatar chloe chlizabe says:

    we all learn from our mistakes ma dear

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