The Dangers Of Sleeping With A Man You Work With

Today I want to cover a situation you’re probably going to run into in life, if you haven’t already. Sleeping with a man you work with, or at least deciding whether or not you should. It’s something that comes up all the time in your emails.

Have you watched the show Shameless?

In it one of the lead characters is/was sleeping with her boss at work. At the same time, she’s also having sex with the boss’ brother. I know it’s only a story but I love how the twists and turns reflect so many things that happen in real life. One of the reasons she’s sleeping with her bosses’ brother is because he’s a badass and she’s used to being treated badly by men.

It’s great character development. I’m enjoying it a lot. So what do you do if a guy in your office starts hitting on you? Do you sleep with him or not?

To be honest, I always say you need to think very carefully before you start sleeping with or dating anyone you work with. Think about it. Work is just like a second home. In fact, most the time you spend more time at work than you do at home. I don’t know about you, but I can’t think of anything worse than coming home, and finding someone I used to date sitting on my couch.

When you split up with someone you work with, that’s what happens every day. You wake up in the morning, head to the place you’re going to spend the next 8 hours of the day, and walk right into the man you had a horrible breakup with. It’s pretty awkward I can tell you.

Here’s the thing…

If you’re thinking of sleeping with a man you work with, don’t just jump right in there. Go out in a large group or colleagues on evening, and see what he’s like in public. People act very differently when they’re out in public, so get outside and see what they’re truly like. You might find he’s a complete ass, in which case your decision is easy!

The main thing you need to do is figure out whether he’s actually interested in dating you, or whether he just wants a bit of fun. Try to spend some time with him before you make any decisions. Talk to him on the phone out of work. Start to find out what he’s all about. You’ll be able to tell soon enough what his real intentions are. Dating people you work with is always a bit risky in my opinion. Think about it this way…

People get bored at work, and flirting with the pretty girl across from you can pass the time. That doesn’t mean you’ll have any chemistry when you’re in a relationship. There’s a very fine line between office flirtation and genuine attraction, so make sure you know what’s going on before you jump into anything serious.

The last thing you want is to have your heart broken and to lose your job at the same time!

About David

1.7 million men & women come to me every month to find the secrets to success. And after 20 years of coaching, I’ve discovered the golden keys to success in dating, business, health and wellness, and life.

I’ve helped millions of men and women around the globe achieve success in their dating, social and personal lives. I’m also a father to the world’s cutest little girl, and I am an unapologetic man. Some say I’m nuts, others say I’ve changed their life forever. One thing’s for certain: I’ll always give you the truth, whether you can handle it or not. I never sugar coat anything.

Nice is so overrated. I’d prefer brutally honest breakthrough to a “nice” rut any damn day of the week. If you’re the same way, then you've come to the right place.

6 Comments | Join the Discussion!

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Laura N

Thursday, February 27th, 2014

Oh, hell no. No way would I EVER date a guy in my office because: Most of them are married. NO BUENO! We would end up talking shop all the time. If it didn't work out: AWKWARD! If it did work out: One of us would probably have to find a new job. Now, many years ago, I worked for a married couple ...and she was his "boss." I remember asking her once how they kept the home and office separate. She told me they had one simple rule... when they pulled into the parking lot at work, they did not talk about personal issues/problems...and when they pulled into the driveway at their home they did not talk about work issues and problems. And having watched them in the office, they did not ever give out a clue that they were married. That particular couple is the exception to the rule. Most of the time it is a bad, bad, bad idea! It's uncomfortable for your co-workers, and you need a little space and time away from your sweetie. It makes you more interesting, and makes the time you do have together more special.

Pam

At my last job, one of the higher up female managers started dating one of the salesmen. People started to figure it out because they were always hanging out in the kitchen together and going out for a smoke at the same time. It seemed like a really mismatched couple to me because she was a snob and he came across as really immature and a lot of his coworkers thought he had Tourette's syndrome as he would just blurt things out loud, including swear words. Long story short, he ended up leaving the company...I'm pretty sure she made him, as no way was she going to give up her high position. I wouldn't mind meeting someone in the same building or office park where I work, though. At least if it doesn't work out you wouldn't have to worry too much about awkwardness. Falling in love with someone or even just dating someone from the same company is a little risky if things don't work out.

Cheryl H

Friday, February 28th, 2014

Not sure which is worse.... 30 years of unrequited love from a co-worker or going for it, get heart broken and move on. BTW: My dad and stepmom met at work and will celebrate 38 years of marriage this year. :)

Guest

Wednesday, March 5th, 2014

I work for an organization where several of the employees are married to each other. It's not frowned on. It's almost encouraged. I have a crush on someone who only sort of works there (he is here just part time, and works through a special program that is part of a strategic partnership with another organization - he's actually an employee of the other organization, not the same one I work for). It's only a crush for now; he's single, and I'm hoping to get to know him a bit better, that's all. So, it's possible to meet someone at work, who isn't technically a co-worker, or a customer. And sometimes, it's actually possible to find a super-friendly organization to work for, where the management not only doesn't mind employees finding love on the job, they sort of encourage it. It just depends on your company or organization. You have to understand the culture where you work. That's priority number one.

Andrea

Sunday, March 9th, 2014

Eight years ago I made the mistake of flirting with a guy at work. I thought he was single because he had mentioned in the office that he had broken up with his gf half a year ago. We went out for coffee twice. On the second occasion he told me that he had told a lie to everybody in the office and that he was just dreaming of making his gf his ex girl friend. I told him that he was a moron and that I felt sorry for his girl friend and that he should never ever bother me again. After that fortunately I changed my job and moved to another branch office of the same company (15 miles away), but he ended up asking my colleagues from my old office frequently about how I was doing. Of course this gave rise to gosspip. I really seriously regret having made this mistake, and I have not flirted with anybody at work since then. I know it can theoretically work out well, but the risks are too great for me. David, your article is excellent.

E

Saturday, July 4th, 2015

I made a mistake of dating my boss at work. The attraction was unbelievable, I tried to deny him but he made a play for me. One day he told me he was in love with me, before he even kissed me & so we started sleeping together. But it was a disaster, he became jealous & suspicious, start treating me like dirt, picking faults in my work. In the end he told other colleagues & of course it travelled round the company. In the end he got the sack & I left my job. If there was anything I regret in my life, this is it.

The Dangers Of Sleeping With A Man You Work With

About David

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