Should I ask out the barista where I get my coffee every morning?

Dear Curbiture,

I work downtown 3 days a week. Every morning I buy my coffee from the girl who works at The Blue Ridge store. We flirt around/talk about c-ville, and she’s always really friendly with me.

But here's the thing: I’m in my forties and she looks like she’s maybe 20. My friend says to ask her out, but I feel like it might be weird.

Thoughts?

Guy in flannel

Dear Guy in Flannel,

Hm. I mean, of course you can ask out anyone you want, but let’s go over the things you didn’t write.

1. She’s at work. Asking someone out at work can be awkward, especially if she’s in the service industry. In addition to this particular crush, have you fallen for girls whose sole job is to serve you before? I’m not saying you pick the girls who are dependent on your approval/tips, just that you might not have a conscience. Think about this girl. And also, while we’re at it…

2. Can anyone really tell the difference between a 17 year old and a 20 year old? You call her a “girl” so naturally I assume you believe there is a possibility for child rape. I’m not saying you go out of your way to have sex with children, but you may want to look into some serious soul searching.

3. “Flirting” is a very ambiguous word. Are you flirting because you’re talking about C-ville or is there more going on? The way you have it written is “we flirt around/talk about C-ville”. Those are not necessarily the same things. I’m not saying you believe all conversation with a woman is loaded with double entendres, but it looks like you might have major entitlement issues. Based on only the facts you have given us, I think there’s a strong possibility you are a dangerous sociopath.

That being said, there’s no harm in asking someone out after work. Just beware if she shoots you down you may lose your comfy morning coffee routine.

Curbiture