Because his self esteem is almost lower the Chantal's IQ.Wait wait wait, if so James and Chantal was engaged and she cheated on him (assuming that's the reason for the breakup) why the hell is James still friends with her??
Or for some unfathomable reason, he still has feeling for her.
Either way, i hope as soon as he stumbles upon a nice, gental, nerdy girl; beachball-eggplant-head will be a distant memory for him
Edit: Ninja chopper @EurocopterTigre