Ask A Guy: Is It Ever Okay To Date Your Boss?

Hey Joel,

I recently started a job at a place where I work for a guy who is only two years older than me, and although at first I thought I was simply receiving special treatment, I get the feeling he’s giving me extra attention, and going out of his way to make sure I feel comfortable around him. As bad as this feels to say, I see us as quite compatible and feel very comfortable just being myself around him, and I try not to flirt back too much, but I can’t help showing my feelings for him & how flattered I am by these gestures. To make matters worse, I have a hunch he is also dating the secretary of our office. Their relationship does seem to be going downward, but even if I can start a relationship with him, how do I do it without turning friends into enemies?


Before we even get into the details of this possible other girl, let’s pause at the idea of dating someone at your place of work. It’s an extremely high risk situation, and in some cases, it may even violate company policies. Even if you two are perfect for each other, the workplace can easily ruin your plans of happiness.

Due to that, the very first thing you need to do is find out if there are any rules against dating within the office. Many companies have rules like this, even if he’s not your supervisor (which is always a no-no). If there is no formal policy, that’s at least one in the plus column, but that’s not the end of the story either.

Dating in the workplace can be very awkward, and people will inevitably start talking. While this isn’t a 100% reason not to date, you do need to consider it as part of the possibly reality. Office chatter is never fun when it’s about you, and try as you might to hide it, people WILL find out. Furthermore, if things don’t work out with him, there’s a good chance he’ll blab private things to his work pals.

That aside, it sounds like this guy isn’t a good idea – at least for the time being. You’ve only been at the company a short time, and even if you’re super subtle about things, you don’t want to get a bad reputation if things go poorly. Also, if you think he might be seeing someone else, absolutely back off. Even if it seems like the relationship between them is ending, do you want to be seen as the reason or just his rebound? Time is your friend here – use it.

If I were you, I’d let things simmer for another month or two. Get to know him better, and more importantly, get to know the work environment. Once you’re sure that everything is in a good place and that he’s the type of guy you’d want to date, with the greater knowledge you have of him, figuring out how to make that first move will be very obvious and easy.

Best wishes,


Joel Freimark has done a lot in life and seen even more. From last minute international travel to bizarre places to writing award winning books, he’s here to bring his wisdom to all your problems. He hosts a weekly advice series on Youtube and a music series also on YouTube. No question is too outrageous or personal, so go ahead and fire away! Follow him on Twitter.

Are you confused about a guy? Do you find yourself wondering, “What is he thinking?” Tell us everything in the comments! And if you have a question for Joel, email him at!

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