Always a thorny issue in any romantic relationship I've ever been in, a partner's sexual past can ruin an otherwise great relationship. And it's never something as easy as the possible disease angle that gets me (in all honesty, I never even consider it). No, my insecurities stem from the fear of having to measure up to somebody... or a lot of somebodies. I spent the better part of my romantic career being the ex-boyfriend that someone couldn't get out of their system; I never wanted to be on that rotten other end (as the guy who had to deal with the memory of someone else's ex-boyfriend). I was used to being the guy who'd done it all, and then some; the ultra-liberal one (well, there are some things even I haven't done... considered them, but haven't done). And then there are all those horrible, ingrained mistruths we're brought up to believe about men and sex (we're dominant, we should go to bed with whores but wake up with virgins... those things that we're not necessarily taught , but still become part of our consciousness, regardless). When it came to sex, I had to be the teacher, or else problems arose.
- Kevin Smith, The Hows and Whys of Chasing Amy
*title from Kara's old blog tagline.