After Dan plays shrink and fails to analyze Chuck's particular brand of psychosis, Chuck decides to hit on a woman at the bar by implying she's a hooker.  That particular pick-up tactic only succeeds in earning the ire of her boyfriend, who Dan then has to punch in the face.  Go Dan, acting manly for a change!  The new BFFs wind up in a jail cell, where Chuck reveals that his dad loathes him because his mom died in childbirth.  Wow, that's kind of dark, isn't it?  Mr. Trout's lawyer bails him out a minute later, and Chuck agrees to help Dan escape the situation without Rufus finding out.

At Fashion Week, B sends all of Eleanor's models home in an attempt to get J in deep trouble.  It's a clever ploy, but Jenny (Taylor Momsen) just improvises and asks Serena and her friends to model instead.  Meanwhile, Bart purchases an artistic photo that Lily once posed nude for, but he doesn't do it out of the kindness of his heart.   He does it so the photo could never leak to the press and cause a scandal.  Lily puts the pieces together and discovers that he could only know about the photo if he had an entire file about her past, which she demands to see immediately.

Evil Serena (Blake Lively) isn't all that evil just yet, so she still worries that Blair will turn against her if she dares to strut her stuff on the catwalk.  Poppy talks her into it, and B even tells her to go for it, which is probably a sign that she's plotting to dump pig's blood on everyone in the middle of the show.  It turns out her scheme isn't quite that terrible.  She just sends S out on the runway in a dress designed by Little J instead of one made by Eleanor Waldorf.  Talk about a fashion faux pas!

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