Season 5
Overview
Will they? Won't they?
Episodes
1. The Intransigence of Love
2019-01-09
Jimmy and Gretchen tell the story of their love to a prospective wedding planner.
2. The Pin In My Grenade
2019-01-16
Jimmy and Gretchen reveal that they're forgoing a traditional wedding, opting instead for a Courthouse elopement.
3. The One Thing We Don't Talk About
2019-01-23
Jimmy challenges Gretchen to tackle some of the responsibilities that come with being an adult.
4. What Money?
2019-01-30
Jimmy unexpectedly receives a large advance and must fend off all his “friends” who just want a piece of the pie.
5. A Very Good Boy
2019-02-06
Jimmy 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.
6. This Brief Fermata
2019-02-13
Jimmy “gifts” Gretchen a week of no-strings-attached sex.
7. Zero Eggplants
2019-02-20
Gretchen and Jimmy make “couple friends.”
8. The Pillars of Creation
2019-02-27
Paul, Vernon, and Becca air their dirty laundry on a weekend getaway.
9. Bachelor/Bachelorette Party Sunday Funday
2019-03-06
Edgar and Lindsay plan the most epic Sunday Funday yet.
10. Magical Thinking
2019-03-13
Gretchen’s anxiety comes to the surface at a major event she’s organized for her new client.
11. Four Goddamn More Days
2019-03-20
Gretchen maintains an elaborate act of deception while Jimmy prepares for the big day.
12. We Were Having Such a Nice Day
2019-03-27
The day before the wedding, Gretchen’s mom comes to town and Edgar takes Jimmy on an epic best-man date.
13. Pancakes
2019-04-03
On the day of their wedding, Jimmy and Gretchen grapple with the meaning of marriage.