Gossip Girl Caption Contest 49

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Welcome back to the 49th Gossip Girl Insider Caption Contest, our Friday tradition. With a record number of responses, choosing a winner was tougher than ever!

We ultimately went with jess_chair4evax as this week's champion. Congrats!

We had to shorten the novel-length winning entry below, but scroll down the list of comments to read it, along with the full array of captions submitted!

Honorable mentions go out to Sammy*, RACOON EYEZ* and chairlover. Thanks to all for playing and best of luck again in this coming week's Caption Contest!


Nate: Hey man, I've been wanting to change my signature scent, I've been trying out a new cologne. I can't decide if I like it, would you mind?
Chuck: (sniffs Nate) To be honest, Nathaniel, it smells a little like desperation.

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Nate: why are you even going out with Vanessa
Chuck: Because she feeds me lots of food that i didnt know about before i came here, like croissants their delicious man
Nate: liking croissants isnt a good reason to stay with someone....do you even think she's pretty
Chuck: Oh heavens no she looks like bob marley but i just really love her food


lmao all of natesbbyxoxo's are far superior to jess_chair4evax's. went something like... "nate: it's not one on one if your the only one playing with the ball
chuck: you would know" :D




@ jess_chair4evax I just love the way you write even when you wrote the last thing about Georgina and Dorota. Your passage about Nate and Chuck was very clever and funny. You are really good at this! Best of luck!


Nate: What?
Chuck: I am not that dirty Nathaniel.
(Chuck walks off. Nate sighs)
Nate: I only suggested a threesome.


Hahaha btw, ILOVEJESS:) is my best friend before you all go off on one!


Jess is NOT making multiple acounts!


Thanks everyone who loved mine! I'm glad I made you all laugh! You guys are awesome! (And real LOL... we'll get to that in a minute...) I see mine is causing some drama here :) I glad. That must mean its really good! To all the haters so think I'm making "multiple accounts" (LOL), as the new Georgina would say, "Envy is one of the seven deadly sins" and as Dorota would say, "God is always watching!" :P
LOL xoxo


Chuck: wat do u think of my new sweatsuit-corporate shirt combo??
Nate: come on man u look terrible.
Chuck: punk! *hits nate in d face*


Nate: Chuck, throw the ball already.
Chuck: Huh? Oh sorry, I got distracted. Everytime I stare at this ball I'm reminded of when I followed Blair to Tuscany but didn't tell her I was there.
Nate: Why didn't you tell her you were there?
Chuck: I had a bad experience with the tanning equipment before I got on the plane. By the time I'd landed...well, let's say, me and this ball actually shared something in common.

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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

[to Jenny] That's the thing. You need to be cool to be queen. Anne Boleyn thought only with her heart and she got her head chopped off. So her daughter Elizabeth made a vow never to marry a man. She married a country. Forget boys. Keep your eye on the prize, Jenny Humphrey. You can't make people love you, but you can make them fear you. For what it's worth, you're my Queen. I choose you.