Jimmy and Gretchen meet at the wedding of Vernon and Becca Barbara. Jimmy, whom Becca turned down when he proposed two years earlier, is convinced Becca only invited him to rub the marriage to Vernon in his face. He nevertheless showed up, determined to ruin Becca's day as payback. Gretchen came as the guest of Becca's sister, Lindsay, who is Gretchen's best friend and enabler of her sex, drugs and rock-and-roll lifestyle. Gretchen is the publicist for a rap trio and lives in a chaotic apartment, while Jimmy can support himself in upscale Silver Lake and drive a BMW, despite having published a novel, written during his post-breakup depression, that has sold little and been remaindered at the local bookstore. He supports himself by writing for glossy magazines, in addition to the tiny royalty checks that occasionally arrive in his mailbox.
He and Gretchen meet as Jimmy is being thrown out of the wedding reception after whispering something offensive to Becca, while Gretchen has decided to run off with one of the bride's gifts, a blender. Claiming to have no interest in a relationship, the two hook up and over the next few weeks, despite setting out to just "hang out and have fun" without obligation, they find themselves coming closer together.
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