You shouldn't say mean things to girls about their looks.
James felt disappointed that Jenna beat him at the chess tournament.
James wants to feel less inferior to Jenna.
James mentally thinks that at least he's more attractive than Jenna, while outwardly congratulating her.
James tells Jenna she's a fat, pimply nerd no one will ever love.
James' ego is soothed without offending anyone, and he keeps practicing to get better at chess.
James' friends laugh, but the chess club advisor overhears and kicks him off the team.