Scott obviously felt something like a womanizer though.
So, whoa huge guilt trip with what I presume was his first sexual experience. Then he's with James - who he's not supposed to be fraternizing with. And then he gets together with Chloe without ever officially breaking things off with James (I have a feeling there was little that was official about their relationship.)
And then he finds out the teenaged girlfriend *didn't* have an abortion, he has a son . . and he's lightyears away and can't do anything about the fact that his kid is being raised by an alcoholic stripper who leaves him home alone for hours at a time at the age of eight. Pretty much his only option for intervention is to get the kid put into foster care (and further ruin the life of the girl who's life he already feels he's ruined), which is no guarantee of a happy family.
In the wider world's understanding of things . . . that's one hell of a run of bad luck, but hardly makes him a womanizer. But from his perspective, given his beliefs and morals and how he was raised? Yeah, I can see that he'd have doubts about himself specifically in regard to his sexuality. It's not the only area of his life in which he doubts himself, but it's been a pretty big deal in the past. So in his alternate, imagined life . . he's a lech. Not because he's slept with a bunch of women in reality, but because that's how he perceives himself.
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