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Gossip Girl Caption Contest 25

Welcome to the 25th edition of the Gossip Girl Insider Caption Contest!

This week's winner is JustMyChuck (with an honorable mention to GGFreak).

Congratulations! Thanks to everyone for playing and submitting a record number of entries, many of which were very, very funny. Good luck again this week!

Serena and Cyrus

Serena: Aaron's a great guy, Mr. Rose.
Cyrus: Well he's sure done a number on you! I taught him everything he knows. I've always said, one girl is just "Not Enough!" It's our family motto. Now where's my hug?


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105 Comments

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  1. Lovingmotherchucker Says:

    Cyrus : Well well well
    My day is getting better and better
    Serena : What do you mean Mr ?
    Cyrus is the name , i thought you know me by now
    (Serena thinking ) : Noo Not realy
    Cyrus : Your dating my son
    S: OMG I diddnt know you would be so small !
    Cyrus : Ah come give me a HUG

  2. M Says:

    WOW, your even taller, I mean prettier, than I imagined!

  3. kay Says:

    Cyrus: Serena give me a hug
    Serena: OMG i should had listened to blair when she warned me!
    there a huggers!

  4. kay Says:

    Cyrus: what do you think of this suit?
    Serena: i think it's a no hugging suit.

  5. UESgirl_forever Says:

    S: Your Aaron's father....wow that is inconceivable.
    Cyrus: Yeah....
    S: And your height...thats also inconceivable
    Cyrus: You keep using that word. I do not think it means, what you think it means.


    Sorry guys, this will only make some form of sense if you have read/seen Princess Bride.
    i

  6. S Says:

    S: Wow, he's small.

  7. Taylor Says:

    Serena: Um, little boy. This is a grown-up party. Where's your mommy?
    Cyrus: Aw fooie, come give me a hug.
    Serena:...um you really should fine your mommy, I mean this is Blair Waldorf's party.

  8. livelylover Says:

    S: OMG you are a gnome!I mean.. you.. are an abonormally nice man! It is such a pleasure to finally meet you!
    C: The pleasure is all mine! Now give me a hug!

  9. JennyAndNateFan Says:

    Serena: So you are Aarons father?
    Cyrus: Yes I am! :D
    Serena: I see that Aaron got your... umf.. smile?
    Cyrus: He sure did! :D
    Serena: But not your height
    Cyrus: He sure didn't! :D
    *Akward moment*
    Serena: Okay.. I'm gonna go now..
    Cyrus: Yeah.. me too...

  10. GGFreak Says:

    Cyrus is looking at Serenas boobs.
    Serena: Eh..Cyrus? My face is up here.
    Cyrus: I know but this is as far as I can look without a broken neck.
    Serena: I'll get on my knees then..
    Cyrus: Good idea!

  11. Genevive Says:

    Cyrus: INCONCEIVABLE!
    Serena: *laughs like a four-year-old awkwardly*

  12. sez Says:

    Gossip Girl VO: Looks like the tortoise and the hare had their destined meeting at last. We all know who wins the race to that special someone's heart.

  13. Olivia Says:

    Cyrus: Come give Daddy some sugar.

    Serena:Oh dear god.

  14. geo Says:

    GGFreak has got 2 win tht made my lol so much :D

  15. chairluverx Says:

    S: hi. ure small
    C: so?
    S: bow down to me.

  16. juicygossiplvr Says:

    Gossip girl: Since when did a hobit escape from lord of the rings? Looks like B didnt get the guy she hoped for and it looks like B's mom has gone a bit blind. Wonder what B's dad and his boyfriend think about the hobit? How he doesnt match their china?

  17. shrimpie Says:

    when the tall and blond me the short and bald

  18. Tanya Says:

    Cyrus: Can you believe that bitch Blair posted a sign in front of her mom Eleanor's bedroom door?
    YOU MUST BE AT LEAST 5 FEET TALL TO GET ON THIS RIDE... Inconceivable!
    Serena: Oh, don't worry Mr. Rose, give Blair time, she'll come around...

  19. Molly Says:

    Serena: OMG, You looked taller in the Princess Bride!

  20. darena Says:

    Cyrus: Oh, I forgot to put on underwear.

  21. enunciiate Says:

    Cyrus: What?
    Serena: I'm sorry. It's just...
    Serena continues to laugh.
    Serena: I can't believe Aaron's going to look like this when he's older!
    Cyrus: What?
    Serena: Thank you. I think I'm going to find Aaron now. I need to tell him I totally understand why he needs to play the field now rather than later on in his life.

  22. Liz Says:

    GGFreak! hahahahaha that person has to win hahahaha hilarious.

  23. T Says:

    Cyrus: Hey Serena. Have you ever seen Clueless?
    Serena: Yes I have. People tell me I look just like Cher.

  24. jlo Says:

    OMG GGfreak yours has to win!!
    it is so funny:)

  25. westwick01 Says:

    Cyrus: "Serena!! Page 6 doesn't do you justice!! You're absolutely stunning!!"
    Serena: "Well thank you, who are you?"
    Cyrus: "I'm Aaron's father, Cyrus"
    Serena: "Oooh ok, I should have guessed."

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