Ok, so basically there is this cute girl who is a part time waitress at this restaurant my folks go to like every week. My folks are chatty and really laid back people and they basically know all of the waitress there and are really cool with them.
Most of the waitress are like 35-45, and my dad is the goofy flirty type and my mom just busts his balls about it, because he's harmless.
Anyway there is one waitress there who is my age, single, and from what I gather share a couple of interests with. And over the course of many dinning sessions, they've told her about me, divorced, with a kid, etc etc, and learned a lot about her, a teacher, a reader, etc etc.
I've only crossed paths with her once at the restaurant. I really suck at picking up IOIs but my dad swears she was interested in me. She was constantly coming over and talking to us, smiling, and telling us stories. When we got up to leave she told me to bring my son in next time.
My issue is I rarely go to that restaurant as it's out of the way for me, and a bit of a pain to bring my son (sometimes)
Also, I am a bit of a pessimist so I think there could just be a chance that she is being nice and what not, but my folks swear that it's more than that.
My dad is dying to drop my number or get her number for me, and that's cool and all, but, I don't want it to seem like I am hiding behind my folks. My dad is smooth and I am sure he could play it right, by saying something like, uhh, sh!t, I don't even know how he could do it, but he swears he could.
However, even if I went in with them, I wouldn't know what to say to her.
Me: Hey my folks said your single, want to get some coffee with one night?
Haha kidding, but really not sure, how to make a move.
The whole situation is a bit screwed, but from what I've seen she seems like a really cool girl, and definitely someone I want to know more of.
Under different circumstances, it would be easier to make a move, but being I don't interact with her it's nearly impossible to build a rapport, and my folks already have a perfect one set up.
The other option I was thinking about is if a number is too forward, I could always exchange email or facebook info, again either directly or indirectly (ie through my folks)
Thanks in advance!