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New York City. The first night of fall. Three women seek love in three very different ways. Sasha (21) is an impulsive young woman consumed by a volatile relationship with a passionate writer, Gavin. After yet another fight, Gavin refuses to play along with their evening plans. Sasha takes off with her best friend instead. Jessie (33) is a successful ad exec searching the Internet for her perfect match. Increasingly desperate, she agrees to meet Frank, an average guy from Brooklyn, but she abruptly ends the date, regretting the whole idea. She tries to salvage her night and looks for better plans.