Narcissistic, brash, and self-destructive Jimmy Shive-Overly thinks all relationships are doomed. Cynical, people-pleasing, and stubborn Gretchen Cutler knows that relationships aren't for her. So when they meet at a wedding, it's only natural that the two of them go home together.

Chris Geere
Jimmy Shive-Overly

Aya Cash
Gretchen Cutler

Desmin Borges
Edgar Quintero

Kether Donohue
Lindsay Jillian

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An episode spanning the course of nearly three years, we see the events that lead up to Gretchen and Jimmy meeting.
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