23 years old and from Boston, Massachusetts, United States
Yes, that's me with Mr. Boston of "I Love New York" fame. My friends and I partied with him and his twin brother when they were in Boston for Christmas last year (or Passover, they're Jewish). Anyway, he is indeed as hilariously awkward as he seems on tv and I had a flashback to the show when he tried to kiss me at the end of the night (gross). His brother is adorable and far more normal.
A: He wants to have sex with you sans condom because it feels better. Don't do it since he may not be clean. He probably doesn't have AIDS, but he could easily have the herp or hpv. If you do sleep with him, don't let him sweet talk you - use a condom!