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I Am Secretly Dating My Boss

Dear Sugar
I recently started hooking up with a co-worker of mine and so far so good. Actually, I don't even know why I am sugar coating it, truthfully, he is my boss. Out of the office, he is everything I have ever wanted in a boyfriend, but when we are at work, it's a hi, bye, and the occasional smile and wink. Our relationship must be kept at a low profile for obvious reasons, but are his actions at work any indication of how he really feels about me?

Over the past few months, my feelings for him have escalated. I am trying to play it cool when we are together, but I think he is catching on. He sends me what I think are flirtatious messages, but I can't tell what they mean since he is so cold to me at the office. Our dates are always very romantic but I have no idea what his intentions are. Am I setting myself up for heartbreak? Will this ever be more than an out-of-office fling? Hopeful Heidi

To see DEARSUGAR's answer

Dear Hopeful Heidi
Office romances are often very complicated, especially if he is your boss. Is inter-office dating allowed at your company? Are either one of your jobs on the line? Do you want to make a commitment with this man if he is willing?

Being coy at work might be best under the circumstances, since you don't want people talking thinking that you are just looking for an easy leg up. I think the best thing to do is be open with your feelings if you want to pursue this relationship.

Since you have been dating for several months, it is about time you have a discussion about the status of your relationship. Find out if his flirtatious hints are advances or just friendly acts in passing. The only way to find out if your relationship will ever be more than an office romance is to confront him about it. This could be an uncomfortable discussion since you report to this man, but it is the only way to get answers you need to satisfy your curiosity.

If you get the response you are looking for, hopefully you can feel more secure with your demure work day exchanges. If he is not ready to make the commitment you are expecting, it might be best to cool down the office heat. I hope everything works out for you.

Join The Conversation
Imabeliever Imabeliever 10 years
If you are serious about one need to find another job. If you stay and it gets serious then someone is going to get into trouble or if it ends badly you could end up destroying his career with a sexual harrasment claim.. too many complications.. just get another job and keep dating or end the relationship..IMO.
jennifer76 jennifer76 10 years
LOL Jinx!! Sounds juicy. :D
Jinx Jinx 10 years
Wish I ~Procrastinate Now! Don't Put It Off~ (Ellen)
kh61582 kh61582 10 years
OK so I understand this situation very well. Currently I'm dating a professor and I'm a college student. (You guys can think whatever you want but we love each other and I'm not some baby who doesnt know what she's doing) When we first started it was like. Sometimes I thought to myself that I must have been dreaming the relationship in the first place because when we were together it didn't even feel like it was going on. That's just the name of the game in a relationship like this. I do think that you should talk to him about it. Next time he "ignores" you at work any conversation you have will probably fly right out of your head but you should just let him know that if he can you could use some assurance every now and then even if it's little things. Good luck!
getstinko getstinko 10 years
I met my wife at a previous job. these days it's hard to meet people to date outside of work. a boss dating an employee is not kosher, the fact that he's your boss makes things very complicated. at my company he'd be fired - no warning, no notice. the fact that he is so cold in the office indicates that he knows he is in dangerous territory. If your current relationship gets messy you could have a major lawsuit. Cubadog's recommendation is correct - if this feels real you need to discuss it with him and tell him you want to move to the next level and in order to do so you will be taking a new job with another company.
cravinsugar cravinsugar 10 years
Cubadog is taking a cold approach to telling you not to expect sign of romance in the office. Dating a boss is walking a very fine line...and he probably stands to lose more than you as far as if the relationship is discovered. I have found out that two of my coworkers are dating by chance...they keep it under wraps here. I met my boyf at a prevoius job and we are still going strong, but there were no anti-dating rules. Just be careful. I'm all in.
cubadog cubadog 10 years
You need to discuss your relationship with him and find out where he stands. If you are going to become a committed couple I would suggest you find a new job. I see nothing wrong with the way he is treating you at work; your their to work not go in his office and make-out. Did you actually expect him to skip down the hall holding your hand?
justjaime27 justjaime27 10 years
Well, it's not the easiest situation, but if you two really care about eachother & keep it under wraps & professional at work, I think that's ok...maybe? I don't know, I married my boss...ha ha. Yes, my husband used to be my boss, I was a cocktail waitress, we started dating, kept it quiet at work, fell in love, moved in together, and got married 4 years later! We've now been together almost 9 years! However, keep in mind I was a cocktail waitress...cocktail waitress positions are a dime a dozen, not sure what kind of job you have, but if it's one you don't want to risk losing, I'd be very very careful. I don't know, I say we can't help who we fall in love with, so go with the flow maybe and see where it takes you. Just be cautious. Good luck!
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