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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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  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...

  11. bob67 Says:

    Jenny's breakthrough fashion choice: a skirt that hikes up to your breasts!

  12. Jordan Says:

    plaid jumper: $56
    blue blazer: $124
    finally realizing you have no friends: Priceless

  13. Avery Says:

    Dan: Duuuuuuude
    Lil J: huh??

  14. Kim Says:

    Dan: Damn, that's a nice ass.
    Jenny: Where!? Where?!

  15. Taryn Says:

    Dan: Yea... well i really don't think me and Serena worked out our problems like we should have. It's just so hard to be with you her. You know?.... Jen?
    Jenny: Oh sorry! Guess i zoned out when i caught my gorgeous reflection in that car window... oh serenas in the car... never mind.

  16. Taryn Says:

    Dan: Yea... well i really don't think me and Serena worked out our problems like we should have. It's just so hard to be with her now. You know?.... Jen?
    Jenny: Oh sorry! Guess i zoned out when i caught my gorgeous reflection in that car window... oh serenas in the car... never mind.


    Note: Sorry i messed up the words on the last one.

  17. chair4evuh Says:

    D-Ohh thats gotta hurt
    J-i dont know with all the botox she probobly couldent feel it

  18. Nat Says:

    Dan: Why are Nate & Chuck making out?

    Jenny: oh being Bi was so last season.....Tila Tequilla! duh.

  19. Gossip Girl Says:

    Gossip Girl: Looks like Dan Humphrey is back to being lonley boy and looks like little J just lost her bank balance

  20. Maddy Says:

    Dan: That dog just pooed on the side walk, a new inspiration for my poetry!
    Jenny: *Sarcasm* yeah Yale will definitely be impressed by that
    Dan: It's unique at least.

  21. Jordan Says:

    Jenny: How do you fall up the stairs?
    Dan: Im not sure ask Serena im sure she could give you a few pointers. she did it last week
    Jenny: Look there she is now ill go ask.
    Dan: Jenny!

  22. kim Says:

    jenny: do i look like a branded material now?

    dan: chuck is way better than serena and all those stuffs...wu wu wu WHAT???


    jenny: ugh. did you kiss him?!

  23. Jordan Says:

    Jenny: Is that a guy or a girl?
    Dan: Um im not sure
    Jenny: Wait thats Chuck
    Both: Wow

  24. Suu,xoxo. Says:

    Gossip Girl: "Do you think Little J's knows you don't have to wear your school uniform once you drop out?"

  25. ^^ Says:

    Jenny : okay... why is that middle aged dressed like a banana school girl? IS SHE EVEN PART OF THE UPPER EAST SIDE???

    dan: chill... that was you a year ago...

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