He might get awkward then, yeah, but don't most people?
Admittedly, the people I've known who use their looks to get things are mostly professional or aspiring actors, not hustlers or con men, but they've had part of their blushiness excised. I'm trying to think of Neal Caffrey getting awkward, and I'm just not seeing it.
For me, Dean stands out as someone who acts much more good looking than he believes he is, or is able to listen to himself being described as.
Gaia for Ellen?
It's not like the guys are all great either--most of the pantheon is kinda pissy.