Tim buddy,
I feel for you. Can I categorically say this is not the way. I mean that in the nicest way possible. There are gig meet up websites out there for you. As a fellow man whatever fantasy you have in your head will not work out.
A) they don't think about having a nice time.
b) they can be very opinionated
c) they will find it weird and/or use it against you if you get personal.
d) they don't want to be you friend
think of it like this, all the decisions that you had to make when starting or thinking about starting punting. She had to make when becoming an escort. In short she's trained herself to put a distance between her personal and work life. You need to do the same.
I almost have someone in mind, but I'm not aiding your madness.
watch this mate.
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