Season 5
13 episodes · Jan 9, 2019
Will they? Won't they?
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S5E1The Intransigence of Love
Jan 9, 201926mJimmy and Gretchen tell the story of their love to a prospective wedding planner.
S5E2The Pin In My Grenade
Jan 16, 201926mJimmy and Gretchen reveal that they're forgoing a traditional wedding, opting instead for a Courthouse elopement.
S5E3The One Thing We Don't Talk About
Jan 23, 201926mJimmy challenges Gretchen to tackle some of the responsibilities that come with being an adult.
S5E4What Money?
Jan 30, 201926mJimmy unexpectedly receives a large advance and must fend off all his “friends” who just want a piece of the pie.
S5E5A Very Good Boy
Feb 6, 201926mJimmy attempts to prove that, despite being on the verge of becoming a married man, he has not lost his edge. Edgar and Lindsay attempt to go on a real date.
S5E6This Brief Fermata
Feb 13, 201926mJimmy “gifts” Gretchen a week of no-strings-attached sex.

S5E8The Pillars of Creation
Feb 27, 201926mPaul, Vernon, and Becca air their dirty laundry on a weekend getaway.
S5E9Bachelor/Bachelorette Party Sunday Funday
Mar 6, 201926mEdgar and Lindsay plan the most epic Sunday Funday yet.
S5E10Magical Thinking
Mar 13, 201926mGretchen’s anxiety comes to the surface at a major event she’s organized for her new client.
S5E11Four Goddamn More Days
Mar 20, 201926mGretchen maintains an elaborate act of deception while Jimmy prepares for the big day.
S5E12We Were Having Such a Nice Day
Mar 27, 201926mThe day before the wedding, Gretchen’s mom comes to town and Edgar takes Jimmy on an epic best-man date.
S5E13Pancakes
Apr 3, 201926mOn the day of their wedding, Jimmy and Gretchen grapple with the meaning of marriage.