Hagubaba, you can get hints at how she feels before you make any moves. Does she acknowledge you by a nod, does she even say "Hello", or does she completely ignore you? That should give you an idea on how comfortable she is with the situation and how delicate you should be when raising the subject.
That reminds me of an escort I was seeing about 10 years ago. A stunning and very bright girl, doing her phD in a field related to International Studies. About 3 years later, I met her in a very senior meeting with very senior officials of the government, where she was now working! She was more beautiful than ever! I felt a quite awkward when I realized she recognized me, but she greeted me like an old friend, kiss on the cheek, asking me how I'd been. Wow! Beautiful and smart! Powerful cocktail! Made me melt! Unfortunately, I never saw her again and she does not escort anymore.... shit!