Welcome to the 40th Gossip Girl Insider Caption Contest!
This week's winner is chucksbabydoll. Congratulations! Honorable mentions go out to Alex, JJ and Sarah. Thanks to all for playing and good luck again next week!

Jenny: What do you think they're doing in there?
Eric: Who, Dan and Serena?
Jenny: Yeah, they're totally hooking up.
Eric: Nah, they're probably just playing dress up with Cedric. After we found out Rufus and Lily used to be lovers, they put on a fashion show for him.
Jenny: Everyone has their way of reconnecting.



February 27th, 2009 8:38 AM
Jenny: Hello.. Eric are you there? Stop loocking at me like that.I'm scared.
Eric: I'm sorry Jenny but when I look at you I wander "Way I am gay?"
February 27th, 2009 9:04 AM
Eric: *says to self* Don't look down. ACT GAY! ACT...GAY!
Jenny: Uh, Eric are you alright.
Eric: Oh yes, I really just love your...dress... *says to self...* NOT.
Jenny: Really, thanks. :)
February 27th, 2009 9:30 AM
Jenny: Hey eric, dont be hurt cause i got a boyfriend... i still like you, but just as a friend ok?!
Eric: well actualy...
Jenny: I know I know, i'm perfect and all, ut please, i'm commited... you've got to stop hitting at me... and staring... althought i'm flattered...
Eric: No jenny you're getting it all wrong...
Jenny: what?
Eric: i was just telling you, you have something in your teeth! You should clean it, it's disgusting!
February 27th, 2009 9:31 AM
(awkward moment)
jenny: so um eric, you wanna like braid each others hair?
eric: wtf jenny i'm not that gay... now i want my latte with extra chocolate on top. and and don't forget the marshmallows this time!
February 27th, 2009 9:35 AM
jenny: ill show you mine if you show me yours
February 27th, 2009 10:03 AM
Jenny: C'mon, everyone's doing it.
Eric: Hooking up with their potential step-sister? Please show me who else in the Upper East Side is doing that!
Jenny: Uh, my brother and your sister? Duh!
Eric: ...I'm not sure I'm comfortable hanging out with you alone anymore...
February 27th, 2009 10:15 AM
Jenny: So my brother is dating your sister, my Dad is dating your Mom and you're dating... Jonathan. What about me??
Eric: Have you met my former step-brother, Chuck?
February 27th, 2009 11:18 AM
Jenny: I'd kill to be a stylish as serena
Eric: As her brother...as your future step-brother...as her stylist....I'd say kay-off the racoon eye shadow and shave your head. Roadkill looks better than your hair.
February 27th, 2009 11:32 AM
Jenny: "So Eric, now that we're related and such, it's illegal to peak in the shower!"
February 27th, 2009 12:20 PM
Jenny: Is that..Chuck's jumper you're wearing?!
Eric: Yea i went through his wardrobe and helped myself
to some of his jumpers and socks while he was on that
bender in Thailand.
Jenny: Really? (starring suspiciously) Cause i'm kind of
missing these 8 inch manolo blahnik's, you wouldn't
have..touched them?
Eric: Me, definitely not.
Jonathon, maybe...