Very interesting!

I can totally see how talking to a therapist/being with a sex worker helps people be themselves because there is not external pressure to be accepted or "perform" well.

However, this seems to also be enabled by the fact that money is exchanged. "I am paying you so now I can be as awful as I want".

This reinforces the idea that if you have nothing to provide (either money or *the pleasure you give people by being a nice person to hang out with*), you won't be liked or accepted. I can't say if it's positive or negative. I think it's important to "be who you are" but I also think that who you are depends to some extent on your environment (1) and that you shouldn't "be who you are" if you are an awful person (2).

In any way, your friend must absolutely confront his fear.