Gossip Girl Caption Contest 39

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Welcome to the 39th Gossip Girl Insider Caption Contest!

This week's winner is Kelly. Congratulations! Honorable mentions go out to both Maddy and kikifromdablock. Thanks to all for playing and best of luck next week!

Lily and Chuck

Chuck: She was beautiful. She had long brunette hair, and a mask. She-
Lily: Oh I know! It was Blair.
Chuck: No, Lily. That was last season’s ‘masquerade’ episode.
Lily: Oh. Okay. Keep going.
Chuck: Anyway, she wore black lingerie, with garters, and-
Lily: Are you sure she wasn’t Blair? I mean, that girl does have more garters than a prostitute.
Chuck: Yes, Lily. I’m sure. Where was I? Oh, well she is older than me, and is a nanny.
Lily: Dorota?!

Steve Marsi is the Managing Editor of TV Fanatic. Follow him on Google+ or email him here.


Ah, thank youu:)very exciting!


i love kelly's and kayleen's!


Chuck: What the hell Lily? Lily: What? Chuck: Did we or did we not agree that our next meeting the colour theme would be pink? *points to vest*


haha this is the season for cougar hunting. HAH.


Lily: What's wrong Charles?
Chuck: Well I was thinking that since Nate had the duchess and Dan has Ms. Carr I was thinking...
Lily (cuts off Chuck): No way.


Chuck: You know what Lily? Your marrige with my father didn't have a horrible ending after all. Lily: Yes indeed Charles, Rufus is a Gentleman! Chuck: I was actually going to say I had inherited not only the deeeds$$$ but a new family.


chuck: do these socks make my feet look nude?
Lily: Nudey feet.. haha


Chuck: Why are wearing all black? Lily: Because of you're Dad duh! Chuck: Seriously Lily, you were planning to scape with Humphrey, you kissed him and slept with him now you're showing 'respect'? Lily: O___o how do you know about me and Dan?


Chuck: (thinking: I should be wearing my purple outfit) Lilly: (thinking: He sould be wearing his purple outfit)


Chuck: (thinking) That's a hot maid. I wonder how she would look like without clothes... Oh, wait. I already saw her.
Lily: So, are you ready?
Chuck: Yeah, whatever.
Chuck:(thinking) I wonder what we are talking about.

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[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.