Loveshy's make the stigma with virginity, no one else does. They make themselves the target of jokes because they make it an issue past high school really no one talks about that stuff. Reminds me of a quote a friend of mine said in regards to sexuality (he's married with kids) "I used to be embarrassed about jacking off, than I finished Freshman year." Once people get to the point it's not super taboo or new or shocking, no one cares, unless you make it a thing.
As Kent mentioned before his lack of understanding to female parts he's probably worried some other dudes "nut" as Kent likes to put it, is just hanging out there waiting to fall on his (by own admission) little, little Kent.
Outside of sexual things, a girl who's had a relationship knows how to date and do couple things etc, for them in all aspects they want to be blind and drive a car with a blind passenger. I think aside the greed, a lot comes from low self esteem.
