All my life I worked in jobs that required me to be friendly , first waitressing and then the medical field.

Coffee shops really have become tricky. I initially thought coffee shops were great as there wasn't a blaring band and booze involved ..

I think its possible that she did want to know a bit about you .. questions about your son ? Has she met him before? Hell, maybe shes interested in him.

I say just pick out a few questions that you might ask her next time you see her. Rehearse them so they are more comfortable to speak...

Maybe ..

You must get tired of being here all day .. do you enjoy going somewhere else to enjoy your coffee... add in a chuckle here ( I wouldn't take that as a creepy question )