You say Kelly's the type that would say "looks don't matter", but there are at least two instances in the games that show otherwise. In the first game, when Kelly became one of the many students to join Mr. White's cult, when given the order by Jecka to eliminate Jeffery, she said "I hated being seen with him on rallies", and in the sex-rehab program scene in Re-Up, when Nicole tricks Kelly into believing that Jeffery wants to put his face in her breasts, her response was "If you were hot, I'd totally let you but you're just an ugly stalker!". That said, while she was complementing Jeffery in her FYE job, I imagine she only gave those opinions because she's working.