Season 5 poster

Season 5

(2019)

Overview

Will they? Won't they?

Cast

Chris Geere as Jimmy Shive-Overly
Chris Geere

as Jimmy Shive-Overly

Aya Cash as Gretchen Cutler
Aya Cash

as Gretchen Cutler

Desmin Borges as Edgar Quintero
Desmin Borges

as Edgar Quintero

Kether Donohue as Lindsay Jillian
Kether Donohue

as Lindsay Jillian

Episodes

The Intransigence of Love poster

The Intransigence of Love 9.0

January 9, 2019

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

The Pin In My Grenade poster

The Pin In My Grenade 9.0

January 16, 2019

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 poster

The One Thing We Don't Talk About 10.0

January 23, 2019

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

What Money? poster

What Money? 10.0

January 30, 2019

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 poster

A Very Good Boy 10.0

February 6, 2019

Jimmy attempts to prove that, despite being on the verge of becoming a married man, he has not lost his edge. Edgar and…

This Brief Fermata poster

This Brief Fermata 8.0

February 13, 2019

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

Zero Eggplants poster

Zero Eggplants 10.0

February 20, 2019

Gretchen and Jimmy make “couple friends.”

The Pillars of Creation poster

The Pillars of Creation 10.0

February 27, 2019

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

Bachelor/Bachelorette Party Sunday Funday poster

Bachelor/Bachelorette Party Sunday Funday 10.0

March 6, 2019

Edgar and Lindsay plan the most epic Sunday Funday yet.

Magical Thinking poster

Magical Thinking 8.0

March 13, 2019

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

Four Goddamn More Days poster

Four Goddamn More Days 6.0

March 20, 2019

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

We Were Having Such a Nice Day poster

We Were Having Such a Nice Day 10.0

March 27, 2019

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

Pancakes poster

Pancakes 10.0

April 3, 2019

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