You know the kind of arrogance that would cause someone to make disparaging remarks about a stranger. And question why he or she has something desirable in their life that they do not.(as if they don't deserve it) hmmmmmm
Not going to lie but this strikes a bit of a nerve as a guy who may or may not be far off from your "dweeb". Who has had a girlfriend that is 12 years younger than I, and quite attractive even for her age(she looks 5-10 years younger than what she is). Would even go so far to say she has an exotic look as well.
Just opining & maybe venting