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Blair's estranged father, Harold, comes home for the Christmas holidays with an unexpected guest: his gay lover Roman. Both Blair and her mother, Eleanor, find it difficult to hide their disappointment while Blair hatches another underhanded plan to get rid of Roman for good. Meanwhile, Jenny and Vanessa help Serena plan the best Christmas surprise ever for Dan, who may have a surprise of his own in mind for Serena. Chuck phones Blair from Europe and informs her that Nate has joined him in Monaco, worrying Blair that Chuck may disclose the details of their hook-up. Also, Rufus refuses to remain the understanding husband any longer after Alison's former lover calls the house.

Harold Waldorf mentions Blair's favorite movie in which a cat is called "Cat". This film is Blake Edwards' "Breakfast at Tiffany's" (1961) starring Audrey Hepburn. The actress and the film are both huge influences throughout the first season with numerous allusions made about them.

This is the last episode to feature Dan and Jenny's mother, Alison Humphrey (Susan Misner).

Dan and Serena sleep together for the first time.

Cedric, Dan's cabbage patch kid, is mentioned by Blair when Serena ask her for help picking out a gift for Dan.