So a good friend of mine (lives in Long Island) is in his early 30s and he's never really dated anyone. Part of this is that he lacks confidence with women and doesn't put himself out there enough.
I was thinking of hiring someone to "be" with him. The goal would be for him to believe that an attractive woman found him attractive enough that she threw herself at him. Thing is he can't know she's an escort.Has anyone done anything like this before? How would I go about doing this

Sounds like an episode of 2 1/2 men.
There are probably a bunch of girls here who would do this, but what happens if he really, really likes her? Wouldn't it be better to be honest with him? Just tell him its about time he got laid, and your going to send over a beautiful young girl for that purpose.

How would the escort screen him?

One thing that defines the difference between sexual assault and actual sex is consent.  It's not ethical to set someone up for an encounter with a sex worker without making them aware of it.  This is a bad idea.  Don't do it.

You sound like a good friend, heroshindo. I'm somewhat like your buddy (see my recent ISO post for a teacher in nyc), but came to the conclusion on my own that a good provider might be helpful.

Just have the provider pretend her husband is out of town or shes here on a business trip. This way your friend knows there wont be a second chance to see her. He will have some more confidence next time he goes out.

Get a pic of his drivers id

I would consider suggesting he hire an escort. She will need to screen him. Also, he may not be comfortable with the fact that she is a sex worker. We all would like to assume eventually people will come around and accept this opportunity as safe, but you have to respect other people's moral codes. I would consider this tricking someone into crossing a personal moral boundary. Do not lie to him