Talk to Me: How to Ask Out a Coworker


Q: How do I ask out a girl that I work with? Is it a good idea?

A: Ah, yes, dear reader. Coworkers are a tricky territory. You spend so much time with them that it’s almost impossible not to feel a connection to them, but you also run the risk of some very awkward encounters if things don’t work out.

I think the first step, and probably an obvious one, is to make sure that there are no rules against pairing up in your workplace. Every company is different on how they handle matters like this, so it can’t hurt to be certain before walking down a path that might get messy.

Once you’ve got that all squared away, then I think you can handle it how you would handle any potential dating scenario. Absolutely ask her out! If you think the two of you have a good connection and there could be something to discover there, then go for it. What’s the worst that can happen?

I’ll tell you. The worst thing she can do is say no. Yes, that would sting and yes, you have to see this person regularly afterward, but it’s really not that bad. If you’re worried about it being awkward after a big N-O, then it’s entirely up to you to make sure it doesn’t end up that way. Tell her that you understand and thought you’d take a shot. Say that you really enjoy hanging out with her and that’s plenty enough for you.

If she’s the one who starts acting strange, then just continue to be your wonderful self. She’ll get over it.

On the other hand, maybe she’s giving out some strong vibes or has made a comment about how cute you look when you get worked up in meetings. You’re feeling pretty confident that she might be interested in you and, since you’re feeling the same, you think it might be a good time to ask her out. You’re wondering how to cross that line from coworker to soulmate.

If the thought of going from the workplace straight to a date seems intimidating, then just ask her if she wants to hang out outside of office hours sometime. It’s a great way to get to know her better and see what she’s like when she’s not under the watchful eye of the person who signs her paychecks. In my experience, everyone is cooler outside of work. It takes some pressure off of things if they already feel comfortable with you when you try to move things in a more romantic direction.

Then again, maybe that’s not your style. In that case, just do it! Ask her out. It only has to be as complicated as you want it to be. No matter what she says, at least you’ll know how she feels and be able to decide whether or not it’s time to blow out that candle you’ve been holding. 

The only bad idea here is to sit around wondering what would have happened if you had just asked her out.

Want some crappy advice?
Submit your questions anonymously here:

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s