I once encouraged a friend to see a prostitute. He was 28, hadn't had a steady girlfriend (and hence sex) since age 19 or so, and some 2nd hand feedback that I had heard was that women found him "skeevy". I suggested that maybe going to a pro once or twice here and there could take the edge off and stop him giving out desperate/creepy vibes. I also gave him a bit of a safety talk, vis a vis condoms and STI screening before and after. I think he did it maybe 3 times over 2 years or so? He seemed to pick ethically, and goodness knows the ladies were definitely charging enough. Anyway, I'm going to his wedding next month, so that's worked out fine in the end. I don't know if he ever told his future-wife, though I imagine he would have. BTW I'm a lady.