The guys are invited to a wedding of a mutual friend. Nick, fearful he will run into his ex-girlfriend Caroline (guest star Mary Elizabeth Ellis), asks Jess to be his date. Meanwhile, Winston takes his role as an usher very seriously and gets competitive on the dance floor with a young guest. Schmidt not only catches the eye of a beautiful woman (guest star Katie Cassidy), but also his “frenemy” Gretchen (guest star Natasha Lyonne) whom he sleeps with at every wedding reception.
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