Dating at work...

I manage an office for a small but quickly growing company. Our office is very small, although we have a presence in several states. My boss's son works with me in the office. We've worked together for a little over a year now. He's single and always making comments about being single. I have really liked him ever since we met but haven't really ever alluded to it. During the Christmas Season he recommended the movie "Love Actually" to me... I just watched the movie for the first time last week. Anyway, to my question... How do I let him know I'm interested without crossing the forbidden line? And is it even possible? I'm thinking that if he was interested, he'd be too shy or worried about legal ramifications to ask. What do I do? I'm crazy about him.


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  • The thing that you have to think about is whether or not you want to take the chance of it possible going sour, then what would you do? What if he turns out to be really vindictive and gets you fired because he IS the boss's son. That's just what I would think about at least. BUT there's absolutely no harm in going for maybe lunch? Or coffee? Something work related, but where you can actually have a conversation and get to really know him if that's what you want. But just know that whenever you break into the realm of office dating, there's always the potential there for your to screw up your job over it, what if he turns out to be a nut and basically forces you to quit? And then you have to see him everyday? That would not be fun for anyone, which is why usually they say its best to steer clear of that, but you never know, love works in mysterious ways I suppose.

  • Hmm, well you could ask him to go for a couple of drinks or something after work one night :) get to talking, be a little flirty! let it show that your interested, because he is most likely interested as well... How do you feel about the whole "you guys working together" + feeling romantically attracted to him? Do you think it would cause problems in the work place? I'm sure you've already asked yourself that, but you would be the best judge of that out of anyone.

    I say, if you guys like each other, go for it.

    good luck!

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