The inaugural Gossip Girl Insider Caption Contest yielded an even 100 replies, so we're guessing you enjoyed it. We'll make it a regular thing.
Now let's take a look at who won ...
You made it very hard to pick a winner with so many good submissions. Honorable mention goes to Gossip is my LIFE, but the winner this week is hellosunshine. Congratulations!
The winning entry appears below the photo. Scroll down the page for the full list of submitted captions this week! Thanks to all for playing the Caption Contest and good luck again this week!

Dan: (on phone) Hey Chuck, we need your help. Yes, Blair's here. No, I'm not telling you what she's wearing! Just be at Blair's in 10 minutes!
Dan: What do you see in that man?
Blair: He's Chuck Bass, duh.



May 30th, 2008 10:06 AM
Dan: Yes, please make the card read "Die, Georgina. Die a horrible death!"
May 30th, 2008 10:26 AM
Dan: Hmm, how in the hell did my life end up this way...
May 30th, 2008 10:28 AM
I am not ready to forgive her yet.
May 30th, 2008 11:02 AM
dan:i just want to forget about the whole situation right now, s and g are just way too much.
blair: well maybe, we...i don't know can talk.
May 30th, 2008 11:12 AM
This is it, Humphrey Dumpty, now or never.
May 30th, 2008 12:03 PM
Dan: Should I get my ear pirced?
Blair: You're kidding, right?
May 30th, 2008 12:12 PM
Dan: I'm all alone...all i have is....(sniff sniff)...Cedric
May 30th, 2008 12:13 PM
Blair: Dan....I have to tell you something...I have just farted!
Dan: Mmmmmm. It smells great B! Do it again!
May 30th, 2008 12:21 PM
Why did you not tell me you liked me before? I always liked Serena...but if you insist.
May 30th, 2008 1:28 PM
Dan : (thinks) hmm... why is blair starring at me?? maybe i look good with this pose..haha.. of course i do..
Blair : (thinks) OMFG,, his ear is soo hideous.. euuwww