Only 14, Jenny Humphrey is the youngest of the Gossip Girl characters. Jenny is the younger sister of Dan Humphrey (Penn Badgley).
She's an aspiring social climber, and while she physically resembles Serena van der Woodsen, she often tries to fit in with the rich-girl clique of Blair Waldorf at her school, even though she doesn't hold a place in their social world, being from (relatively) middle-class Brooklyn.
Despite her lack of clout, Jenny managed to steal Nate Archibald from Blair Waldorf at one point, and dethroned Blair to become the de facto new social queen herself for a brief period.
Young and insecure but spunky and driven to get what she wants, "Little J" often goes to wild and embarrassing lengths to set up an image for herself, which causes much consternation for her brother Dan and father Rufus (Matthew Settle).
Near the end of the first season, Jenny began dating a boy named Asher Hornsby to help climb the social ladder. However, it turned out Asher was gay - and mean. This episode resulted in the outing of Serena's brother, Eric van der Woodsen.
Jenny Humphrey was also busted stealing clothes from one of Blair's rich friends.
Too bad it's more than our rent. But I think I can sew something like it.Jenny
Jenny: So we should just be anonymous losers who eat lunch alone and never get invited to parties?
Dan: Works for me.