Best approach (and this works in strip clubs, too):
In your next conversation with her, work the conversation casually around to you sort of complaining about being stressed (work, hours, whatever). Then volunteer that you're bummed because there's an escort that you've seen for years who you had an appointment with but she had to cancel because her kid was sick. Casually say that appointments with her are your much-needed stress relief, that you have the cash for her burning a hole in your pocket but you don't know what you're going to do now.
Then. . . leave the subject alone. All you have done is put something on the table and walk away from it. Very non-threatening. You haven't invited her to do anything. You haven't suggested anything. All you have done is complain a little bit, and mention a subject that she may or may not know anything about. She's then free to ask questions about that subject. Her questions, or lack thereof, will tell you everything you need to know.
If she's curious, she'll ask questions ("Escort? What's that?", "What do you do when you see her?", or "How much does she charge?") and the conversation can go from there. Sometimes they'll point-blank say they've thought about it (or even would like to try it) but didn't know how to get into it safely. Refer her to this website or some other review site if you want. At that point you can just roll with the conversation.
Originally Posted by Racerunner
I would not recommend this approach. This has a great chance of working in strip clubs because the strippers are part of a sex industry, they just are not necessarily providers. A civilian on the other hand, would need a much more cautious approach. The problem with this approach is that JG may not want to be outed as a hobbyist. He may want more discretion. JG has met this woman in class and if the lady takes the approach you mentioned the wrong way, then she may report it to school officials. It doesn't matter that he never actually made a quid pro quo offer, they may see it as reason enough to expel him from the college.