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Gossip Girl Caption Contest 20

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.

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38 Comments

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  1. rachel Says:

    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.

  2. Jasmine227 Says:

    Dan: I never noticed how hot chuck is.

    Jenny: Is that why you went over to see him?

  3. Pernille Kjaersgaard Says:

    Dan: Ooh! Did Regina George just get hit by that big yellow school bus?!

  4. Pernille Kjaersgaard Says:

    Dan: Would you just look at that girl's ass! Big, round and juicy.. mmm.. I would love a piece of that!

    Jenny: Dan, stop.. Not even Chuck Bass is that vulgar!

  5. mere24 Says:

    Dan: Damn, Serena is looking hot!
    Jenny: OMFG, where did she get her shoes?!

  6. gigi624 Says:

    LITTLE J : DO WE HAVE ANY FRIENDS ANYMORE?
    DAN: NO, I'M BACK TO BEING LONELY BOY.

  7. juicygossiplvr Says:

    J: Uhhh, great, im hangin out with my brother again. i guess my dreams of being queen b r squashed

    D: Why the hell did i break up wi serena?? i will never be able to get a girl like that again!

    other girl: Uh, is little j? I cant believe she tried to be one of the girls like blair and serena! honestly! she lives in brooklin aswell.

  8. Brian Taormina Says:

    J: Why in the world is that girl wearing a yellow cardigan while holding a pink binder?
    Dan: ........

  9. Westchester Says:

    Jenny: These pedestrian lights take so long...
    Dan: Can you read that poster on the Bus?
    Jenny: Yellow is so last season(unless you wear Laboutin or Furla). Dan! don't stare. Use your peripheral vision.
    Dan: That's what the poster said?
    Jenny: Nnn... Yeah! (I guess my uptown knowledge doesn't work well with Dan)

  10. Sebastian Amezaga Says:

    Dan: Omg is that Britney Spears...?? She's hot again...
    Jenny: (If only he knew britney thinks he's a HOMOnizer)
    Dan: Let's see I think I'm a womanizer....
    Jenny: Here we go again.... Priceless...

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