Helpless in human resources

Please send some holiday-related letters. And other letters. But I love holiday letters. This one almost counts.

Hi there! I'm kind of in a silly predicament. I have grown a lot at my company in the last five years. I'm very happy there and can see myself in my job for a long time.

I have been single for a while after a six-year relationship, and have found sparks with a coworker. Even though we are professional when we see, speak, or email each other, I can tell there is a hint of flirting on both sides. I want to be bold and give him my number so we can possibly see each other outside of work. However, working in HR, I don't want to come across as being forward or desperate.

I don't see this coworker every day, and we are Facebook friends (if that means anything), but the company is so small and like family and I don't want to ruin anything, if that makes sense. So, what is the best way to pull the trigger? Am I over thinking this? Should I just shut up and go for it? Or continue being professional? Or am I just rusty and should look elsewhere to date?

– Helpless in HR

Well, you're in human resources, so at least you know the rules. It sounds like dating would be allowed – assuming you're both into it, of course.

How do you figure out whether he's into it? Focus on developing an out-of-work friendship first. Gather a few people for a drink outside of the building. Take advantage of the office Christmas party and talk to him about what he does in his spare time. If you can establish a social connection outside of the office, even in the context of a group, it'll be easier to get answers to awkward questions.

If his motives are still unclear after an outing or two, you can always use your HR title as a conversation starter. As in, "This might be the HR person in me, but I want to ask whether it would be weird to invite you to a movie." Sometimes it pays to be transparent.

You say you want to be bold, but for now, I'd stick to breezy. "Let's all get together after work" is a good place to start.

– Meredith

Readers? Bold? Breezy?