Welcome to the 52nd Gossip Girl Insider Caption Contest, our Friday feature for an entire year now! Thanks you all for playing each week and making this a fun Friday / weekend tradition, and making this the web's #1 Gossip Girl fan community.
This week's Caption Contest winner is xBlairAndChuckx. Congratulations! Honorable mentions go out to O.Le, downtownBassgirl and shadow243.
Thanks to everyone who played and good luck again this week!
The winning entry appears below ...

Vanessa: How did Serena get such a great picture?
Dan: Maybe she’s born with it, maybe its Maybelline.



May 22nd, 2009 8:10 AM
Dan: Hey, there isn't specified my name! What can only mean that...
Vanessa: ... That you're not graduating?! You have to talk to the principal and see if it is not one of the dirty deeds of the gossip GIRLZ!
May 22nd, 2009 8:23 AM
Dan; So after this you wanna go..
Vanessa; nope!
Dan; But look the hotel room even has a jacuzzi
Vanessa; Just because i slept with chuck doesnt mean im the new Nate, dan.
May 22nd, 2009 8:28 AM
Dan: Hey look they're serving my dad's famous chilli =)
Vanessa: Oef, well I think you had some yesterday, what is that smell?
May 22nd, 2009 8:59 AM
Dan: Hey, V, isn't that you and Chuck having sex?
Vanessa: Oh, God.
May 22nd, 2009 9:01 AM
-Let's see, are we going to die next season?
-I don't want to die before having sex with Chuck again!
May 22nd, 2009 9:34 AM
Dan:Vanessa can you go brush your teeth and hair
Vanessa: NO i like looking jamaican and having bad breath
Dan: But no one else likes seeing you anymore
Vanessa: i dont care i just really dont like being clean
Dan: i dont know how ed stays with you
Vanessa: easy i just feed him my lucky grandmas croissants and he eats it all up in just one minute
Dan: WOW
May 22nd, 2009 9:40 AM
Vanessa: (laughing) Look, they misspelled your name
Dan: And they put Nelly (Yuki) Humphrey?
Vanessa: So much for your Upper East Side education.
May 22nd, 2009 10:26 AM
Dan: Hey! My name isn't in here! I have to go find out about this immediately.
Vanessa: You got into Yale, and you lost that. You were about to graduate high school, now apparently you're not. Ha ha, it sucks to be you. Thank God I never went to high school!
May 22nd, 2009 10:36 AM
Dan: apparently the script says your going to die while backpacking with Nate through Europe this summer
May 22nd, 2009 10:59 AM
Dan:... I don't see my name.
Vanessa: I don't see how that's a problem. I thought you hated this school? It's filled with fake, trust-fund dependent children.
Dan: *pause* I'm sorry, who did you sleep with again? Twice?
Vanessa: OH! Here's your name! It's under the catagory of 'Calling the Kettle Black'.
Dan: So it is! And look! You're the club presedent!
Vanessa:... I'm going to find Nate...jack-*ss.