What you won't learn from "The Office"
1/8/2013 9:00:00 AM
Your office could get as awkward as this photo.
Q: I work with someone that I have had my eye for awhile. I asked her out about 6 months ago. She at first accepted and then later in the day she changed her mind. I have not really talked to her much since then except "Hi, good morning," etc. Since the holidays I have talked to her more than I have in the past. She seems like she has been receptive to our conversations. I still like her and I think if given a chance we would hit it off if we went out. Should I ask her out again or keep building on our conversations that we have had when we have seen one another? What should I do?
A: First, a warning: Tread lightly. You're combining two very large and important aspects of your life; your job and your personal life. If things don't pan out, you'll be one miserable fellow.
That said, I'd give it another week before going for the jugular. People tend to be a bit cheerier after a decent holiday break, so she could just be floating on a post-Christmas glow. A little more time may give you a better hint of what she's thinking.
If she's still being more friendly than usual, ask her out. If not, back off. And if she says no, back off even more. Office relationships are sticky quagmire, especially for women. We worry about the professional consequences of a relationship going south, or even the consequences of simply rejecting someone's advances. Hell, we even worry about the relationship doing well, but then not being taken seriously because we're dating a coworker (however untrue that suspicion may be). Meeting a stranger and going on a date is a much safer bet. If we don't like them, we never have to see them again, but a jilted guy we work with is in our lives every day. Even if the break-up is amicable, you'll always have that hanging between you.
If she says no, chances are that she doesn't see the potential relationship worth the risk of messing up her professional life. Things can get really ugly where sex and work intermingle, and I don't just mean the silent treatment or curt ressponses in meetings. Multiple advances can sometimes seem like harassment, and simply coming up with a polite rejection can be very stressful, so go easy with this second ask-out. A simple "do you want to get drinks sometime?" will suffice, and if she seems uncertain, give her an easy out. If she isn't sure, she can still think about it after your conversation and change her mind. But once you push too hard, she'll be scared off for good, and you don't want to have to explain to your boss why things are awkward between the two of you... or worse yet, why she filed a complaint.
Jim and Pam and Michael and Holly may have worked it out, but that's with the magic of television. You're going to need a very light touch.