Mixing Business With Pleasure: 8 Things I Learned After Sleeping With My Boss

Let’s just get right to it. If you have a good looking boss, there’s definitely been some flirtatious passes at each other, or maybe just a wink that sent butterflies throughout your entire body. Hell, he may not have done anything (yet), but you still find yourself thinking about him in more ways than one. There’s something about the way he carries the confidence of three men in one, and the way he wears his suit and tie everyday. What woman in her right mind isn’t attracted to a man in a fitted black suit?

I get it, I totally get it. It’s all about the thrill, isn’t it? I mean, he’s the epitome of unavailable and you always want what you can’t have, right? I’ve been there, and when I say I’ve been there, I mean like in his bed at night, both fumbling to get our clothes off as fast as we can (might I add very drunkenly), and waking up in his shirt the next morning just to take it off again. Scandalous, I know.

That morning, I showed up to work 30 minutes after him – even though we drove together – so it didn’t look suspicious, and as our work day began, so did our exchanging of flirtatious smirks and seductive stares. Followed by a gentle hand on the lower back and a risqué ear whisper whenever we were alone in his office. Then, toward the end of my work day, the raunchy text of what he wanted to do to me after work is read, and I began blushing and crushing so hard. People started to ask me “Who’s the guy?”, because there was no hiding my glow or smile. We continued to see each other after work for a while, up until speculations started going around about us. Then we had to lay low for a while. We agreed to keep things “professional” for a week or so until the rumors started to die down. Finally came the night where we booked a hotel room outside the city, and we could finally act on all the thoughts we had both been suppressing.

I showed up to our hotel room in a long black coat with high heels on. Underneath? Victoria Secret lingerie that I bought specifically for that night. I knocked, he opened up, and I pushed him inside, dropping my purse and kissing him with enough passion to start an actual fire. He pulled away and asked me to get on the bed. Obviously, I got excited because of where my mind was wandering. He offered to take my coat and I let him. He was left speechless, but continued to sit on the bed, at least 2 feet from me. Something was wrong. My heart started to pound, and not in the good way. I shut down immediately and remember hearing something along the lines of, “Listen, I’ve been thinking about us. You’re such an amazing girl, but I don’t think we should keep doing this, not while I’m your boss. I care too much about my job, and don’t get me wrong, I care about you too but if we didn’t work together, I would date you in a second.”

Just like that, we were over, whatever the hell we were.

Though it may have ended between us, we still found a way to work together, even after 2 years since we last had sex. Because of him, and what we had, I learned 8 crucial life lessons from sleeping with my boss:

1. There’s the risk of losing your job. Even though I know I got lucky with my situation, because we still are very flirty and I consider him a good friend, the risk is still there. If corporate ever found out, we could both still lose our jobs. You need to decide if it’s worth it.

2. You shouldn’t tell anyone about it, especially your co-workers. To this day no one knows about us, not even my best friend (and I tell her everything). The more people who find out, the higher the risk of your secret finding its way to the wrong people. If you two have respect for each other, you’ll keep it to yourselves.

3. In most cases, it gets you nowhere. You’re in it for something, and so is he. Whether it’s to get ahead or to give/get some head (LOL). Just because he’s your boss doesn’t make him any different from the typical guys you swipe right to on Tinder. He’s still a guy.

4. It’s just for the moment, and it changes nothing. I didn’t get a job promotion or a raise, nor did I really want one. And I didn’t get the relationship I swore it would’ve turned into, which I did actually want. Like with anything in life, your expectations should be realistic.

5. If things end, keep it professional. If you can remain friends, then do it. There’s no better feeling knowing you can go through something like that and keep your relationship business professional after. Also, don’t avoid each other completely, that’ll only make your co-workers even more suspicious.

6. There’s something romantic about you two having a secret that only you know about. (Assuming no one else knows, or found out). Still to this day I’ll find us talking about that first night and how much fun it was. Or we’ll joke about how we can never have shots of Jack Daniels around each other ever again. He’ll ask me if I remember something in his house and then tell me a story about it, or we’ll catch ourselves reminiscing on all our old, but pretty amazing memories.

7. Even years later he is still very protective of me, which is…nice. If he sees one of our clients getting a little too friendly with me, he won’t hesitate to speak up. And if we happen to be leaving work around the same time he will walk me to my car since our parking lot is very creepy, especially late at night.

8. Sure, it’s an easy thing to regret doing, but don’t. No matter how it ended, or if it did at all, you shouldn’t regret it. It’s a part of life, your life and his, and if you learned anything from it then you should consider it worth it. 

Though most would consider what I did was unprofessional and stupid, I would have to strongly disagree. Nothing bad came from it, therefore, I have no regrets and I know he feels the same way. We are still friends, we can work together professionally, and we can still joke about it years later. We both agree that if we ever need each other for anything at all, that we will always be there for one another. We also know that we will support each other, whether it’s in each other’s careers, love life, or anything else that may occur.

If my boss ever ends up reading this, thank you. Because of you I had some of my favorite memories. And you should know, every single time I see you at work, I still think about our very first night…

Disclaimer: I decided to write this piece anonymously, not because I’m worried about people knowing my story and what they’ll think because I honestly DGAF. But I am protecting my boss, his job, as well as mine, and I’d like to keep our workplace drama free. I just felt like this kind of thing happens more than we think, and instead of feeling wracked with guilt and regret, we should embrace it, learn from it, share our stories, and move forward.

Featured image via RODNAE Productions on Pexels


  1. I just broke up the affair with my boss – literally just last night. I needed to see this as being positive as I don’t feel that way right now.


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