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!

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?!

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