Wow, I haven't seen this pattern in years and years. "Girl falls for the rapey bastard who harasses her" used to be a staple in shoujo manga, but they pretty much dropped it and, you know, good riddance. Not gonna follow this.
this mangaka has not really had any first hand experiences with this LOL
that's not how you do a cold approach on a girl
you can only cut corners if you're extremely athletic and handsome, otherwise being too direct like that does not work, specially in that situation
this kid is too much of a twig to pull that off and the way he talked is weird, meaning the mangaka doesn't really have the experience with this sort of stuff
you need playboy friends to write about playboys, or be one yourself (clearly not the case here)