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So... I need some advice. There is a new(ish) girl in my office (she's been there about a month) and I want to befriend her. Pretty much everyone else in the office is married with children and she's young and single like me. She seems pretty cool, we seem to have a couple things in common. But, I have no idea how to approach her to see if she'd want to ever hang out outside of work.
I imagine this is how people feel when they want to ask someone that they like out on a date... something else I have no idea how to do. I am ridiculously shy and awkward around new people so I don't know what to do or say without looking like a total dork. Not that I'm not actually a dork (I totally am), but I don't know if that's the best first impression to make. (I usually bring that out later on.) Anyway, despite being the girl who ALWAYS made friends with the new kids in school in elementary school, I am now a 29-year-old who has no idea how to make friends and is afraid to talk to new people. I feel like all my friends were pretty much by accident; either someone decided to befriend me, or they started out as a friend-of-a-friend.
Anyway, so yes... I need some advice. Have you made work friends? How did you do it? Should I just bribe her with cupcakes?
At 29 years old, what you call being a "dork" is really just you being a genuine, interesting person! I'd start with that first. Don't be phony!
The "pals" I've gained through work all had at least one common interest outside of work that I did. Try to seek common ground and then expand upon that. Eating lunch together can't hurt either. If that doesn't work you drug her, kidnap her, and then refuse to release her until she acquiesces to all your demands!
Posted by: Daniel O'Leary | August 3, 2009 10:50 AM

I've been in the same situation working with a bunch of married with kids I hoped for a year to befriend someone. Finally we were both in the same meeting which ended right around lunch and I asked if she wanted to grab lunch, she said yes, we talked more than ate for the hour and a year later she is one of my best friends. Wish I spoke up sooner. No need to make a big deal of, do you want to hang out outside work? She might already have tons of friends. I would just start by being her friend and that amount can grow. My two cents worth.
Posted by: Lise | July 31, 2009 12:16 PM