While browsing LordoftheFlies.org (which is also pretty weird, you should check it out) I found friendsbeyondthewall.com It's a service to find Prison Pen Pals. ...yeah. Apparently it's more of a dating service because they tell you physical descriptions and what kind of person the inmate is searching for. They actually let you search for Gay, Bi, Straight or Transgendered/Transsexual people which it better then some dating sites (so I've heard, it's not like I browse them all the time)
So anyway here are some of the best intros I've found:
I also found another one (not screencap worthy) where the guy was serving a 35 year sentence. Descriptions like that really make me wonder what the hell these people did. If some one was arrested because there a pedophile or some shit, I don't think I'd even want to talk to them. Or what it there a serial killer and they're looking for their next target? Some people are even in solitary confinement.
This website is also home to "Composite Magic Photos" but that's a post for another time.