One of the most personally frustrating aspects of Chris' life is how he interprets stories from movies and TV shows as completely realistic. Chris learns about the world from his TV mostly, and his adult persona is made up of adult swim references, vague caricatures of men from commercials and video game stereotypes. Chris has probably seen plenty of shows or movies that deal with sexual virginity, and they're usually painting the virgin as a loser, inexperienced and missing out on everything. Rather than having any sense of self worth, Chris had decided that virginity was his cross to bear until he could find someone to take it from him. What's funny to me is that he had all these conditions for a girlfriend including ethnic background and average intelligence, but felt a prostitute is an acceptable way to begin his sexual history. Most girls I know wouldn't willingly date or hook up with a guy who they know to frequent hookers. This didn't bother Chris though, he broadcasted it to the world. No doubt he was disappointed in the experience, as I'm sure he thought there were Playboy bunnies just waiting for him on the Backpage. I imagine he had his first time with someone who looked like a cleaning lady. Considering Chris has a thing for familiarity, comfort and pleasure with minimal effort, he'll probably be devoting a portion of his tugboat to a friendly, understanding hooker for years to come. Realistically this is the only way that Chris can continue having any sort of sex life that isn't just him masturbating alone in his childhood bedroom.