This episode is a flashback of the three years leading up to Gretchen and Jimmy's first meeting.
- Chris Geere as Jimmy Shive-Overly
- Aya Cash as Gretchen Cutler
- Desmin Borges as Edgar Quintero
- Kether Donohue as Lindsay Jillian
- Janet Varney as Becca Barbara
- Todd Robert Anderson as Vernon Barbara
- Allen Maldonado as Paul Jillian
- Brandon Mychal Smith as Sam Dresden
- Darrell Britt-Gibson as Shitstain
- Allen Maldonado as Honey Nutz
- Shane Francis Smith as Killian Mounce
Beginning with Jimmy's disastrous proposal to Becca a few years earlier, we see the events leading up to the present day.
Emerging from a pretentious radio show interview where he plugged his new book, Jimmy meets the homeless Edgar in an alley and offers him a "lounger on the deck" not realizing that Edgar will accept the offer.
Gretchen is hanging out and doing drugs with Lindsay at a recording studio, sent as a "gofer" by the PR executive handling Sam Draper's rap trio. Sam, who is furious with the executive for not showing up, hires her to do his PR instead.
She attends movie openings with the rappers and meets a well-known director, with whom she starts a relationship fueled by drugs and booze. This results in her DUI arrest the day before Becca's wedding, where she meets Jimmy.
After they break up, Becca tries to proposition Jimmy to pay Vernon back for ignoring her, but Jimmy turns her down. Edgar walks out on Jimmy, saying that while he was with Gretchen he was actually a "fun person".
Gretchen tries to go back to doing drugs at the studio with Lindsay, but realizes it is not what she wants anymore. She goes back to her apartment to set it, and her life, to rights. Jimmy is left alone in his house, trying to write a novel or a song, but unable to do either.