Dating Your Boss: OK or not?

Question

Thanks for all your interesting answers on my previous question re age gap relationships. This is sort of a follow-up question. Is it ok to date your boss? Have you done it? (you might have guessed it- yes it's about me and yes my boss is older than me). He is in a relationship with a woman, he's been with her for 7 years and they have a kid. However, they have been in a serious relationship crisis for quite a while now and i think it won't be too long until they will break up. Before you're gonna say it - i won't go interfere, because it wouldn't be fair.

Nonetheless, my boss has been flirting with me and if he made a move on me i'm not sure whether i could resist. They place i work at is small with only 5 employees.

Please don't tell me i'm a *****, because i'm not planning on grabbing him off his woman. But he's hot. And if he'll break up with her....

what do you think? have you dated your boss before?

Answer 1

I've dated a boss of mine. Heck, even the girl who worked my job before me -- she quit because she married my new boss! Go for it. Just remember -- work is work, relationship is relationship. And wait until he ends it current one before you move in on the prize.

I actually work with my fiance -- he's not my boss, but we met here and have been together for 2.5 years. Studies show that us overworked Americans are turning more and more to workplace relationships and employers are becoming okay with it.

Answer 2

I haven't dated any bosses I've had, but I've known some people who did, and it wasn't a pretty picture. You're in a tough spot to be sure, but I think the question you need to ask is if you should be dating this guy at all. I know you're not going to "grab him off his woman", but it's quite possible (even highly probable) that he's flirting with you because he's unhappy with his current relationship. Wether you have feelings for him or not, he's in a pretty big mess right now that could drag out for months and years, and even if he left his woman tomorrow, you would most definitely get drawn into the problems that were to follow.

My advice to you would be to date other people and forget about your boss for a while. He obviously has a lot on his plate and his intentions are skewed because he's unhappy and he shouldn't be flirting around if he's still in a relationship. If he's been in a relationship with someone for 7 years but is flirting around before it's even over, who's to say he's not going to give you the same (or worse) treatment? The best thing you can do is to turn your attention elsewhere and let him settle his problems. If you really like him, then wait for him to resolve everything (and REALLY resolve it, including legal issues he's likely to face involving his kid) and then see where you stand. For the moment though, this guy sounds like he wants some sugar with you before standing up and being a man and taking care of his responsibilities, and why would you really want a guy like that who's just as likely to flirt around with other women when he's with you if things aren't up to par with what he wants? I wish you luck, and if you really have your heart set, then wait, but otherwise I'd say this guy sounds pretty immature and irresponsible and should be avoided if you don't want to get hurt or drawn into the fights that are sure to happen if he leaves his woman. Best of luck

Answer 3

Well I personally think it would be wrong for you to make a move, whether he's still with the woman or not, but if he asks you and it's what you want, then go for it. But you have to be ready for some changes at your job if there should be a breakup. Make sure that you don't depend on this job too much before getting involved, because it could be awkward and lead to a rocky future.



Be Prepared for anything in any office relationship.

Answer 4

Hi, dating your boss is ok, dumping him at a later date might not be so ok. I don't think you are bad for liking him, but please be aware that if he is capable of cheating on his wife when she is the mother of his children, then he will probably do the same to you, no offence intended, but to him you are further down the rung of the ladder than him, his wife or his child. please don't let him play you for a fool. Yes he probably does find you attractive etc but don't let him use his position of power to intimidate you. Just be careful, you could end up very hurt and jobless. Also don't do anything at all until he has split from his wife, let him sort that out first. You don't wanna be second choice. You don't want to know he is going home to her and making love to her after he made love to you and vice versa. It isn't fair on her either. Don't let him think you are easy pray.
Good luck with it.
ps b_switek gave a really good answer. Take on board what he said.

Answer 5

Keep well away! He's got too much baggage & problems! You seriously don't wanna be dragged into it where, most likely, his woman points the finger at you and lets the world know that you were the reason of her family's break up do you??! If he's gonna break up with her it'll happen in its own time and I think out of respect for her he should be single for a while afterwards...... He'd probably need some 'space' anyway....

Answer 6

I did this years ago and you are looking for trouble. When it all comes down you are gonna be the one known as the "formerly employed" home wrecker! How do you know that their lives aren't going good? I hope that's not something that he's telling you but you don't know first hand. I have a lot of friends that cheat and one thing they all swear when they meet someone new is that they are gonna leave, but they never do, especially when children are involved! Sorry if you don't like what I've said but it's true. :-(

Answer 7

I have never been with my boss, but i have had one of my bosses come on to me, i refused him because he was my boss. anyway i would not do anything with this guy until he has been broken up from that relationship for some time. even though they are having problems they are still together so even though they break up they could get back together. so for now just be friends.

Answer 8

Don't do it. Let him clear his slate first. If he clears it for you, that shows he has honorable intentions. Then, provide him with your resignation, ask for a good reference, and quit. Then you can be free to date him and have no pressures beyond those of regular dating. (Of course, you will always know he's the kind of guy who flirts with the girls at work while still in a relationship with the mother of his child.)
Don't date him. Tell him to "back off" if you like the job; or quit the job and date him.

Answer 9

Hello? Anyone there? Big no! Just freakin tell him to take care of his family issues first...and if he's already like this being married...need I say more? If you really must have this hot guy, wait til he's officially done w/his drama, then do the guy, if it's really that important to you and if you just can't find any other hot dude..it's not cool to be one of those that you're saying you're trying not to be...

Answer 10

Well, if he's still in another relationship then u should just wait for it to be over. Plus, if u do date him, u shouldn't make it to well known, u should be careful because everyone is gonna thing you are sucking up to him. No one will appreciate you if they think that.