It all depends on what kind of guy he is. Nobody but myself and occasionally my fiance drive my Mustang, hot-rod or Escalade. I let her drive the Mustang/Escalade because I trust her plus she is on my insurance. =P
Also, the more expensive the car the more he trusts you. For instance I would let basically anyone drive my car if I owned a 1989 Honda Civic. I have to trust you significantly more if I were to let you drive an $82,000 Escalade. Know what I mean?