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Gossip Girl Caption Contest 25

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

To play, just think up your best caption(s) for this Gossip Girl photo from "Bonfire of the Vanity," click "comments," and post as many as you like!

We'll announce the winner next Friday. Good luck ...

Serena and Cyrus

Gossip Girl Caption Contest 24

Welcome to the 24th edition of the Gossip Girl Insider Caption Contest!

This week's winner is Nico. Congratulations! Scroll down to see the winning entry below the picture, as well as the full list of captions submitted this week.

Thanks to all for playing, and good luck again this week!

Jenny and Nate Dating?

Lily: You're with Jenny now? Good grief Nate, you sure get around.
Nate: Calm down Lily, you'll get your turn soon enough. *winks*
Lily: [giggles]
Jenny: Uh, I'm standing right here ...
Lily: Be quiet Jenny, the grown-ups are talking.

Gossip Girl Caption Contest 23

Welcome to the 23rd edition of the Gossip Girl Insider Caption Contest!

This week's winner is Charlize. Congratulations! Scroll down to view the winning entry, as well as the full list of submissions we received this week. 

Thanks to all for playing! Good luck again in this week's edition ...

Discarded Dan?

911: 911. What is the emergency?
Dan: 911, someone loves Chuck Bass.

Gossip Girl Caption Contest 22

Welcome to the 22nd edition of the Friday Gossip Girl Insider Caption Contest!

This week's winner is de valois. Congratulations! Scroll down to see the winning reply and all those sent in last week, and good luck again in this week's contest!

Chuck and Bart Bass

Chuck: Aren't you going to talk to Serena about going out in that dress again?
Bart: It's not the dress I have issues with... I'm trying to see if she's not wearing underwear again.
Chuck: She's not.
Bart: [stares]

Gossip Girl Caption Contest 21

Welcome to the 21st edition of the Friday Gossip Girl Insider Caption Contest!

This week's winner is sydny. Congrats! The winning entry appears below. Scroll down to read the full list of entries, and good luck again this week!

New Haven Can Wait

S: "Hey, Blair, I think I found you the perfect date!"
B: "Who? Having anyone I can call a date will be an excellent conversation starter the next time I see Chuck."

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.

Gossip Girl Caption Contest 19

Welcome to Gossip Girl Insider and the 19th Gossip Girl Caption Contest!

This week's winner is Meg. Congrats! Scroll down to see the winning entry.

Thank you all for playing and making us the web's #1 Gossip Girl site!

Father-Daughter Clash

Rufus: I just don't want you making the same mistakes I made.
Jenny: Don't worry dad; I don't plan on trying to seduce my son's grilfriend's engaged mother.

Gossip Girl Caption Contest 18

Welcome to Gossip Girl Insider and the 18th edition of the Gossip Girl Caption Contest.

This week's winning entry was sent in by Westchester. Congratulations. Funny stuff.

The winning reply is below the pic. Thanks for playing and good luck again this week!

The Clique

Amanda: Blair and Serena, how come you two aren't having lunch?
Blair: Well, Serena doesnt know how to eat with chopsticks, she's blonde...
Serena: Well, Blair isn't eating because she has eating disorder.

Gossip Girl Caption Contest 17

Welcome to Gossip Girl Insider and the 17th Gossip Girl Caption Contest!

This week's winner is Paul. Congrats! The winning entry appears below!

Thank you to all for playing and best of luck again in this week's edition.

Nate and Vanessa Photo

Vanessa: You mean now you're charging me for a date?
Nate: Well I gotta make a living. And my mom needs to reupholster the sofa.

Gossip Girl Caption Contest 16

Welcome to Gossip Girl Insider and the 16th edition of our Gossip Girl Caption Contest!

This week's winner is thelma. Congratulations! The winning reply appears below the photo.

Thanks to all of you for playing and good luck once again in this week's Caption Contest!

B and S Converse

Serena: If I sneak by really quietly, maybe Blair won't notice my hideous dress!

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