As for your last question, I only do this with you is the most reliable cliche in spa world. After, you're so big, you come so much, and we will do that next time reply to any service request.
That being said, people are people, happy and sad, honest and deceitful, lonely and withdrawn, but just as likely as confused as anyone else in a given moment. You are in the room with the lady, you have been in the room with other ladies: is there anything that makes you feel this one's feelings are genuine? And if so, what are your own feelings? It is easy to feel flattered by someone's interest, but is it something you really want to act upon? And what is your current situation and the risk vs reward calculation from a rational, non-emotional perspective? Answer those honestly (and above all else, to thine own self be true) and then decide if you want to proceed.
OG has a long history that he shares here in a pretty unvarnished fashion, particularly the difficulty of knowing and dealing with facts: the lady is engaged in the activities inherent to this line of work.
In the end only those we care for can hurt one us. For me, I also keep my cards close to the vest, even so, I will add one last little bit of Tennyson: Tis better to have loved and lost than never to have loved at all. Regrets, I've had a few, but then again, too few to mention...