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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Hi. Good site.

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Hi. Good site.

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Jenny: How about that chick over there?
Dan: Ooohh yea nah

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WOW oh my god serena looks freaking hot and way too sexy for my liking

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Dan: I dont know Jenny, Im not doing too well since..
Jenny: Shut up, im pulling my catwalk face and not listening to you. Maybe that girl to our right wants to hear

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Dan: I dont know Jenny, Im not doing too well since..
Jenny: Shut up, im pulling my catwalk face and not listening to you. Maybe that girl to our right wants to hear

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Dan:Uhh!! there is Serena .......i just wish i could have her back
Jenny:Serena's the new queen......well i guess it won't be that easyy
Other girl:Ohhh Queen S is here!!

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Jenny: Dan why the eff are you carrying that lame man-purse??? Dan: Somebody took their happy pills this morning! (under his breath)at least I don't look pregnant... Jenny: Whatever... just go find your friends.....oh wait Dan begins to cry...

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Jenny: Is that girl in the gross yellow cardigan following us? Dan: Um, that's my gi-ffriend Tara. Jenny: Then tell your gi-ffriend it's New York, not ninth grade.

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Jenny: "Please distract me from noticing that sad yellow cardigan thing that is so last season..." Dan: "Wait. Yellow is LAST season...?"