He gets elaborate with Britney. “I have a half million dollars to donate. Please tell me more about the charity you gave yours to. I think it was called… the Brigade.” Hee! Her Diary Room response is really funny, but it’s all in the delivery. Next he asks Joe “How does it feel to be the old man of the house? Oh, sorry Boogie. I didn’t see you there.” Poor Ian gets “For a chemical engineering student, it’s amazing how little chemistry you have with… the ladies.” That would have been ten times meaner and a hundred times funnier if he’d specified Ashley. “Jenn, you have a lot in common with a gossip magazine. You’re both covered in bad ink.” Which is pretty good, but Jenn is less amused it by it than the rest. He makes a joke about Frank’s Little Orphan Annie hair, which is pretty easy.