I'm just going to post a few guesses.
IQ of a genius... Michael
Juvenille offender... Bradley. (Only because the sentence reads I am, not I was. And his "boarding school" may have been a condition).
Fear of birds... the vet guy (Ray?), because Ryan is too obvious, and getting into an area to deal with that phobia makes sense to me.

Fired from every job... Ryan
Dated 100 women... Ben (?) Only because he's the oldest, and dating doesn't mean slept with.
Millionaire.. The dreadlock guy. (George?)
No gf since 11... Josh.
Sorry I'm still catching up with their names.