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Season 5

Season Overview

Will they? Won't they?

Episodes

The Intransigence of Love

1 - The Intransigence of Love

Jimmy and Gretchen tell the story of their love to a prospective wedding planner.

The Pin In My Grenade

2 - The Pin In My Grenade

Jimmy and Gretchen reveal that they're forgoing a traditional wedding, opting instead for a Courthouse elopement.

The One Thing We Don't Talk About

3 - The One Thing We Don't Talk About

Jimmy challenges Gretchen to tackle some of the responsibilities that come with being an adult.

What Money?

4 - What Money?

Jimmy unexpectedly receives a large advance and must fend off all his “friends” who just want a piece of the pie.

A Very Good Boy

5 - A Very Good Boy

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.

This Brief Fermata

6 - This Brief Fermata

Jimmy “gifts” Gretchen a week of no-strings-attached sex.

Zero Eggplants

7 - Zero Eggplants

Gretchen and Jimmy make “couple friends.”

The Pillars of Creation

8 - The Pillars of Creation

Paul, Vernon, and Becca air their dirty laundry on a weekend getaway.

Bachelor/Bachelorette Party Sunday Funday

9 - Bachelor/Bachelorette Party Sunday Funday

Edgar and Lindsay plan the most epic Sunday Funday yet.

Magical Thinking

10 - Magical Thinking

Gretchen’s anxiety comes to the surface at a major event she’s organized for her new client.

Four Goddamn More Days

11 - Four Goddamn More Days

Gretchen maintains an elaborate act of deception while Jimmy prepares for the big day.

We Were Having Such a Nice Day

12 - We Were Having Such a Nice Day

The day before the wedding, Gretchen’s mom comes to town and Edgar takes Jimmy on an epic best-man date.

Pancakes

13 - Pancakes

On the day of their wedding, Jimmy and Gretchen grapple with the meaning of marriage.