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."

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