Gossip Girl Caption Contest 20

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Welcome to Gossip Girl Insider and the 20th Gossip Girl Caption Contest!

This week's winner is Rachel. Congratulations! The winning entry appears below. Thank you to all for playing, and best of luck again this week.

The Humphrey Siblings

Jenny: OMFG, is that dad? He's dating Headmistress Queller?!
Dan: Yeah, well, since you don't want to go to school I bet it's his way of bringing school to you.

Steve Marsi is the Managing Editor of TV Fanatic. Follow him on Google+ or email him here.

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Gossip Girl Quotes

And who am I? That's one secret I'll never tell ... You know you love me. XOXO, Gossip Girl

Gossip Girl

Chuck: I'm sorry for losing my temper the night you told me Louis proposed to you. I'm sorry for not waiting longer at the Empire State Building. I'm sorry for treating you like property. I'm sorry I didn't tell you I loved you when I knew I did. Most of all I'm sorry I gave up on us when you never did.
Blair: Thank you.