Gossip Girl Caption Contest 186
Welcome to the 186th Gossip Girl Caption Contest at TV Fanatic, where readers submit their best caption(s) for a photo from the CW drama! Ready to see who won this particular edition?
Your Caption Contest winner is Kylee Pyle. Congratulations and well done.
The winning entry appears below. Honorable mentions go out to Aquariuz, Amie and heavenscent9222. Thanks to everyone for playing, as always, and best of luck next week!

“Hello, ladies. Look at your man, now back to me, now back at your man, now back to me. Sadly, he isn’t me, but if he stopped holding onto old engagement rings, he could be like me. Look down, back up, where are you? You’re on the Upper East Side with the man your man could be like. What’s in your hand? Back at me. I have it, it’s a box with two tickets to that masquerade that you love but did not live up to the hype. Look again, the tickets are now party invitations. Anything is possible when your man is a Basshole and has an unrealistic writing staff. I have a Monkey.”
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December 21st, 2011 10:56 PM
@kylee Pyle
That's hilarious!!! I love the very last line and the slight jab at the writers!!! I hope yours wins. I don't even think I should try lol.
Rank: Guest Star
December 21st, 2011 4:13 PM
Chuck: I'm considering buying us matching Armani Christmas sweaters.
Monkey: It's better than having matching pink ties...
December 20th, 2011 1:12 PM
@Sarah : Thank you! I was watching the Old Spice commercial when I logged on. :)
December 20th, 2011 5:23 AM
@Kylee Pyle: yours is fabulous! haha
December 19th, 2011 9:45 PM
chuck: monkey dont make it obvious your looking at serenas boob job
December 19th, 2011 3:48 PM
Chuck: It would be awesome if I had a monkey named Dog.
December 19th, 2011 1:49 PM
Would you like to touch my Monkey?
December 19th, 2011 2:59 AM
Chuck: I know Paris and Tinkerbell are wearing matching dress, but we're hotter, Monkey.. waaay hotter.
December 19th, 2011 12:36 AM
“Hello, ladies. Look at your man, now back to me, now back at your man, now back to me. Sadly, he isn’t me, but if he stopped holding onto old engagement rings, he could be like me. Look down, back up, where are you? You’re on the Upper East Side with the man your man could be like. What’s in your hand? Back at me. I have it, it’s a box with two tickets to that masquerade that you love but did not live up to the hype. Look again, the tickets are now party invitations. Anything is possible when your man is a Basshole and has an unrealistic writing staff. I have a Monkey.”
Rank: Guest Star
December 18th, 2011 5:29 PM
Blair: Who's your friend, Chuck?
Chuck: This is Monkey. He was a stray.
Monkey: *thinking* Actually, I prefer "domestically challenged".