If he's living in LA and remains unaware of the life-- well, that's hard to believe. There seems something private about engaging in the hobby, despite all the frat-talk and glib jokes on the boards. Your friend seems to have more complicated problems than just bad luck with women.
I would sound him out pretty thoroughly before opening my mouth with, "I know! Why don't we get you a hooker! Wouldn't that be fun?!
If what he's looking for is a relationship, this ain't the place to find it.
Are you sure your friend's bad luck isn't due to something like being gay?
Taking up the hobby is one thing. Being led into it is something else.
IF you take him into this, find him someone mature, close to his own age. And pick someone YOU haven't had a session with.
DON'T suggest that the hour or two you set up for him is IN ANY WAY the answer to his "problem." It's jus something to do, like getting drunk or going bowling.
Ask yourself, is he unduly neurotic? Does he cling to strong religious beliefs? Does he hate women? If so, then introducing him to the hobby could have very negative results.
If he comes to dislike himself for engaging in the hobby soon or later, will his self esteem fall even further? Would he blame you?
It sounds like his psyche is already on thin ice. So... Ask yourself, if you really want to help him, is this truly the best way?
Or-- I'm not suggesting this is the case-- is this just an excuse to share the hobby with a buddy so you'll have someone to compare notes with and reinforce your continued activity in it.
What if he felt guilty about having a night out (and that's not as corny an idea as you might think) and decided to hurt himself? Would that be possible? Would you be okay with that?
The idea has probably occurred to him sometime in the forty years he's been tramping around on this earth. If he's refrained from experimenting, there is some reason.
Hope this help you make up your mind.