Asking Girl's Mom to Arrange a Date

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Visitor's Question:
I go to this small breakfast restaurant by campus and last year their was a cute girl that worked there. At the time I was seeing someone and her coworker had mentioned she was a high school senior (there's a 26 month difference) when I asked about her.

Since then she has stopped working there but her mom is my usual waitress when I go in for breakfast. Her mother is very friendly towards me and has told me a lot about her daughter because we are going to school for the same subjects, just different schools. Since she doesn't work there anymore I feel like her mom is my only hope to meet her.

I wanna be respectful about it and since her mom likes me I think it's not to bad of an idea. Her mom has also told her about me and I guess she knew who I was (only by my usual order) but since she was never a waitress there she must've noticed me at some point and I made an impression. Should I ask her mom about setting us up and how should I do it.

Our Suggestion:
I would approach this extremely cautiously. You don't want to turn her mom into a gatekeeper.

Instead, simply broach common interests. If there's a movie coming up the daughter might like, mention to the mom that you were thinking of going and ask if the daughter had any feedback on it. I.e. start the dialogue going. That way the mom can ask the daughter and if she hasn't seen it, you can say "hey well maybe we can go together" so it's nice and casual.

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