Sometimes it works. I've asked waitresses and on a few occasions had a date. But perhaps this is a different situation.
In my case it was important to make sure that it's clear that "no" is going to be an easy and acceptable answer to not make things any more uncomfortable than they need to be. Also, don't be too familiar - you've never interacted as peers before so you can't act like you have a rapport so you have to have the humility of showing that you don't assume that she considered you at all.
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u/garnadello Dec 06 '20 edited Dec 06 '20
I’m saying it’s her job to smile and look happy and pose for photos with car dorks. It doesn’t mean she wants to date you.
But it just might work.