Jenny Humphrey, Gossip Girl Season 4 Episode 6
Jenny Humphrey is the kind of character most people love to hate. She started off as the good girl foil to Blair Waldorf's domineering Queen Bee. With her long golden hair and pastel clothing, she was pretty much the picture of innocence. Come Season 4 and she is the next iteration of the Evil Queen of Constance Billard. Dressed in black leather and bleach blonde everything about her as she is reintroduced seems to scream good girl gone bad. Though of course we know much of this character's makeover was due to Taylor Momsen's own personal style. Little J definitely didn't stay little for long.

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Gossip Girl
Gossip Girl Season 4 Episode 6: "Easy J"
Jenny Humphrey
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Gossip Girl Season 4 Episode 6 Quotes

Serena: No shame. For your information we just stayed up talking.
Blair: Oh. So does this chatty insomniac have a name?
Serena: Colin. The Cab Stealer.
Blair: Oh, well you showed him.

Blair: What have we here? Bed: unslept in. Hair in... missionary disarray. And yesterday's dress with today's shame all over it.