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!

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."



October 17th, 2008 11:53 AM
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."
October 17th, 2008 11:55 AM
Blair: [thinking] At least i don't have to flash everyone to get into Ivy.
Serena: [thinking] at least i have intelligence...is that a bee
October 17th, 2008 12:43 PM
Serena: I really hate the headband
Blair: Go back to your drum circles and herbal enlightenment
October 17th, 2008 1:34 PM
S: smile B, you might be my unidentified FIEND in tomorrow's Page Six.
B: it's better than Darth Vader beside Barbie.
October 17th, 2008 1:37 PM
S: smile B, you might be my unidentified FIEND in tomorrow's Page Six.
B: I'D RATHER BE Darth Vader beside Barbie.
October 17th, 2008 1:43 PM
Serena: Is that a christmas present ribbon?
Blair: Oh, S, just because i actually brush my hair in the morning is no excuse to be...jalouse.
October 17th, 2008 2:15 PM
B: What couldn't find anything more sluttier to wear?
S: Oh, this is the most clothing I've had on in years. Besides I have to wear something impressive since I'm going to get photographed.
B: Please, Even Chuck's old dirty whores wouldn't wear that to Headmaster's party.
October 17th, 2008 2:22 PM
Serena: Look Blair, Chuck is proposing to you
Blair:Oh lord!I finally won this game
October 17th, 2008 3:07 PM
Serena: Nothing you do to me will be worse then be stealing your answer.
Blair: Bitch,please.
October 17th, 2008 3:10 PM
Serena: Nothing you do to me will be worse then me stealing your answer.
Blair: Bitch,please.
October 17th, 2008 3:31 PM
*after the fight- back inside*
Blair(sarcastic whisper): I see your heal glued on pretty good.
Serena(Sarcastic harsh whisper): I see your headband found your head again. Unless, of course, you lost that too.
Blair(whisper): Oh, Serena. You should know that my head is not something that runs away on its own. Although, you might want to keep yours screwed up, we never know, it might just explode of over-thinking. Oh, and I always carry back-ups.
October 17th, 2008 3:33 PM
S: You look kind of calm for not having a good answear to the deans question.
B: Did you honestly think I got all the way upp to New Haven without a back up? Besides youre the one who should be nervous.. Your answear might not be that perfect.
http://litenmanual.se
October 17th, 2008 4:31 PM
In their minds..
Serena: Oh great Blair is here!
Blair: No one messes with Blair Waldorf, she is in for a surprise.
October 17th, 2008 4:55 PM
Serena: (thinking) I wonder if Blair realises she has something on the side of her face?
October 17th, 2008 5:18 PM
Gossip Girl:
This looks like a new showdown in New Haven. The Serena vs. Blair cat fight is getting old, wonder when they'll realize it, and if it isn't soon enough, I think they'll both get a slap. A slap on the face that is.
October 17th, 2008 5:26 PM
Gossip Girl here look who we have at S and B in a meeting in Yale will S take it away from B like she always does or is S going to play nice
October 17th, 2008 6:15 PM
Gossip girl here..whatever happened to quiet lunch dates and simple parties for these two it seems all thats happening involves s taking something of little consequece from B whats next for World War 3 ?
October 17th, 2008 6:20 PM
Blair: GOD Serena, you take everything from me! My mum, Nate, my friends and now Yale! You want everything that's mine!
Serena: Err... well..That's not true sweetie... I didn't want Chuck.
October 17th, 2008 11:49 PM
Blair: *thinking* Aren't we sooo cute together
Serena: *thinking* God I want to rip that fugly headband off
her head!
October 17th, 2008 11:50 PM
Blair: *thinking* Aren't we sooo cute together?!
Serena: *thinking* God I want to rip that fugly headband off
her head!
October 18th, 2008 5:18 AM
blair: oh no he did NOT just compare me to Summer from the OC!
serena: just smile and wave, B... just smile and wave...
October 18th, 2008 7:55 AM
Blair is in the middle of an announcemt
Serena: Do you know that your skin looks good? What product do you use?
October 18th, 2008 8:47 AM
*talking through their teeth*
Blair: You're such a bitch.
Serena: No, you're the bitch! Now be quiet.
October 18th, 2008 8:52 AM
*whipers*
Blair: You have no idea what I'm going to do after this.
Serena: Let me guess, his name starts with a C.
October 18th, 2008 8:54 AM
*whispers*
Blair: You have no idea what I'm going to do after this.
Serena: Let me guess, his name starts with a C.