I feel that in his early years he was young an inexperienced, all about duty and getting everyone out alive. Not exactly his own man yet and I can definitely see the "Teen Hero" aspect. When 4 came about he was a lot more relaxed and confident in himself, with that classic Capcom wit that resembled Dante's or Ken's (SF). he even complains about Ada through it, even beats her in a fight and tells her how it is. Ashley never had a chance because either in belief or circumstantial evidence, No one ever had a chance with Leon, he's too wrapped up in his work. At the time Ashley just happened to be the work, so I'd say she took it the wrong way? I think many girls didn't dig that deep and figured he was a hotty for being untamable. Then in Degeneration we all wondered one thing.... W.....T.....F Capcom!?