Jimmy discovers that Gretchen has been sneaking out of the house at night and suspects she's having an affair. Lindsay's life spirals as she discovers she doesn't know how to live on her own. Edgar takes Dorothy out on a date.
Jimmy attends Becca and Vernon's baby gender reveal party. Meanwhile, Gretchen takes care of some unfinished business. Edgar and Dorothy's relationship reaches a turning point. While, Lindsay confronts Paul.
Gretchen enlists the gang's help to deliver some bad news to Jimmy so she doesn't have to albeit derailed by celebrating with an epic day-party. Lindsay comes to terms with stabbing her husband and finds a way to convince herself she loves him.
At a wedding together for the first time since the day they met, Jimmy and Gretchen's tensions come to a head. Edgar's relationship is jeopardized by his newfound success. Lindsay is forced to come clean to Paul.
After Jimmy returns to Los Angeles, he attempts to make amends with Gretchen, leading to their first confrontation. Lindsay and Edgar enjoy their new friends with benefits arrangement while Edgar tries to show Jimmy that Gretchen wasn't the only person he abandoned.
Jimmy learns that his literary novel is being marketed as erotica. While doing Vernon's podcast, Gretchen realizes she's been letting Jimmy off easy. When Edgar and Lindsay babysit Tallulah, Lindsay learns for the first time that she's capable of love and Edgar tries a new technique to pick up women.
Gretchen has moved back into the house and plays mind games with Jimmy, sabotaging his first interview for the new book. Seeing an opportunity in Gretchen's return to the house, Edgar and Lindsay plot to get Jimmy and Gretchen back together.
Jimmy goes out of town for a book convention; Gretchen decides to throw a divorce party for Lindsay, leading to an unsuspected visit from Paul; Edgar's friend encourages him to overspend on party planning.
Lindsay's mom comes to town, shedding light on the origin of Lindsay's issues, while Jimmy attempts to get over Gretchen by hooking up with someone from his past. Meanwhile, Edgar struggles to reconcile his new writer life with his old veteran life.
Jimmy spends a day with a woman from his past and attempts to fit in with her friends; Gretchen tries to impress Boone's ex-wife; Lindsay reconnects with a former father figure; Edgar buys a car that he cannot afford
Gretchen becomes a part of a family tradition with Boone and his daughter. Jimmy goes on an NPR game show. Lindsay's desire to help leads her back to Paul. Edgar attempts to make a deeper friendship with Max.
Gretchen spends the day with Boone and his daughter in an attempt to distract herself from having slept with Jimmy the previous night, while Jimmy tries to prove to himself he's moved on. Lindsay attempts to save Olivia from getting too close to the unreliable Gretchen, and Edgar trails Max to figure out why they're no longer writing partners.
Jimmy and Gretchen go for a long drive to force a conclusion on the confusing state of their relationship. Edgar finds closure with Max while Lindsay figures out a way to solve Becca, Vernon, and Paul's problems all at once.