Conversation so far:
How does Season 1 start off?
In the pilot episode, Chuck attempts to rape both Serena and Jenny Humphrey.
Who are Serena and Jenny Humphrey?
his step-sister at the time, Serena.
Did he succeed after attempting to rape them?
he attenuates his behaviors as a sexual predator and becomes more of a manipulating womanizer.
Did he try to rape anyone else?
CANNOTANSWER.

Question: Did his womanizing ways catch up to him?
Self-contained rewrite: Did Chuck Bass's womanizing ways catch up to him in season 1?