He had a great relationship with Amber (the woman to whom I referred). Smugness found no place in his character—though I will admit he was often insecure. I think you've misunderstood that he saw her as some kind of trophy girlfriend. That wasn't the case at all. Amber wasn't a model, had no interest in being one. But she was tall, slender & very attractive—physically the type.
I wanted to point out that Aaron, my son, always treated women with respect. In contrast to Umair's assertion that men can only score with attractive women if they behave like douches.
I made a lot of mistakes as a parent, but that is one issue I got right. Of course it also helped that his mother is a strong, intelligent woman:)