You know, this conversation reveals some interesting things about Chris...
The first, he apparently has no sex drive, which is something I've suspected for a long time. He claims to have had sex with his prostitute twice, and then that's it. No longer interested in sex. It goes a long way towards bolstering my theory that he's simply a man child who saw getting rid of his virginity as a rite of passage into manhood, but never really cared about it. It also explains why he gets condescending when he thinks his "friend" is still a virgin. Chris views himself as successful in something because he managed to fulfill a simply biological act. One wonders if he feels just as accomplished for breathing or going to the bathroom... actually knowing Chris, that probably is a big achievement for him.
The second thought that crossed my mind is that he seems very hung up on this women being "Cherokee." I do wonder if she actually is though. It's not uncommon for people in the South to claim Cherokee ancestry, and certainly its true for some people. However, I wonder if she might be black or mixed race. In the past, it was very common for people of mixed race to claim Cherokee descent due to the stigma of being black, even amongst other blacks. Of course, Chris wouldn't know ethnicity by looking at someone, but I think it would be freaking hilarious if Chris had sex (or attempted sex) with a woman of African descent, as that's one of the criteria he specifically excluded from his "Love Quest."