2) You date. You break up. He dates someone else and brings her to your holiday party. You get drunk and do a disastrous karaoke rendition of “I Hate Myself for Lovin’ You,” then inappropriately grope your assistant. HR puts you on probation.
3) You date. You break up. He becomes your boss. Or you become his. Awkward.
4) You date. But you don’t break up—oh no, you get married, EM. WTF??! This might be the worst possible case scenario because then you never get a break from him. Until you get divorced. And guess what? You still work together even then! What fun!
Work should be a place where you can focus on work and not have to deal with the insecurities that dating often brings. There are plenty of other “full packages” walking around out there; they just may be less readily apparent than your hot coworker’s package.
The straight man’s perspective: Chris Kennedy
Imagine me, if you will, wielding a sickle, because I will be playing the dating advice grim reaper this month. It’s not because I think I look good in black, or because I have a fondness for wearing hoods and showing up unexpectedly during your day … though that might be interesting. No, I’m playing that role this month because you April questioners have forced me to.
EM, I can’t imagine you haven’t heard the common warnings about dating co-workers. “Don’t dip your pen in the company ink.” “Office dating if Off limits.” And the more direct, “Don’t s#$% where you eat.”
I don’t see much of an upside to this for you. IM flirting is one thing; acting on it is a whole other thing. Here’s what I see if you act on this and go out with him. You IM him one day. “Wassup? R U up 4 drinks l8ter? (Smiley face, wink.) He replies, “U buyin’? JK. LOL. Sure.” You reply “K. TTYL.”
So, you two go out a few times, fool around, carry your little office secret around for a little while and it’s all exciting and sexy. Then word gets out and you’re in the office gossip fodder.
