Billy hits it off with a new man, only to find out he's a "participator"; Julie's home life crumbles as Arthur cracks under the pressure of the PBS pledge drive.
Billy visits his very Jewish brother for Yom Kippur dinner; Julie attempts to befriend a veteran to prove to Marilyn's surrogate daughter that she's charitable.
When Billy’s apartment is condemned, he moves in with Marilyn; a misunderstanding lands Julie a role on a TV show. Rachel Dratch guest stars as a casting director. Abby Elliot guest stars as an Internet executive who offers Billy and Julie a trial job.
As her birthday gets closer, Julie discovers that she enjoys her mom's company when they are drinking; Billy tries to date a guy he met through an app.
Julie and Billy jeopardize their shot at becoming fashion elites when Julie gets sick and Billy gets cast as the lead in a children’s TV show. Christian Siriano guest stars as himself. Austin Pendleton guest stars as a tightly-wound television director.
Julie writes an essay that is optioned for a movie, Billy helps with Matthew’s wedding. Julianne Moore stars as a development executive. Richard Kind stars as a writer who helps adapt Julie’s essay. Amy Sedaris and Deborah Harry return as roommates.
Having maxed out on antidepressants, Julie faces a family Passover Seder armed only with a meditation app. Meanwhile, Billy gets a gig as a warm-up comic for Larry Wilmore's new late-night talk show and Arthur heads to Florida for work.
Julie faces a moral dilemma when she gets cast in Woody Allen's new TV show; Billy and Marilyn scam their way through a government gay conversion therapy program. Matthew's ex-wife comes to town.
Julie decides she has an addiction to her mother, and treats it by joining AA. Billy helps his sister-in-law Rucchel exorcise a Jewish demon from her basement. Arthur experiences frustration in the bedroom and at work, and takes both into his own hands.
Alone for the weekend, Julie hires a creepy handyman who overstays his welcome. Meanwhile, Billy feuds with a dickish advertising exec, and Marilyn gets a book deal.
After cut-rate facial filler leaves Julie's face frozen into a smile, she savors the unexpected benefits. Billy has the opportunity to teach acting after running into his favorite school teacher, and Marilyn wants Julie to freeze her eggs.
Julie and Arthur stumble into sexual roleplay, while Billy worries he's been miscast as a supportive spouse at Todd's work parties. Meanwhile, Julie's dogs become social media stars without Julie's consent, and Marilyn re-unites with a former lover.
Lifelong dreams come true when Julie gets hired to write on a TV show, Micky Dolenz answers Billy's childhood fan letter, and Marilyn throws herself a Bat Mitzvah.
Julie “Yes Ands” her way into a corner with her former improv teammates and ends up being caught in a significant lie. Billy and Todd can't fall asleep in the same bed together. Meanwhile, Arthur uncovers a secret at work and Marilyn and Matthew bond.
Julie considers trading her showbiz dreams for a life of happy crafting as Billy sickens of New York City. Arthur is over his job, and Marilyn experiences writer’s block. Meanwhile a visit from Lola’s sorority may hold the answer to all of their problems.
Billy moves to Los Angeles with Julie's help. Marilyn writes a best-selling memoir, also with Julie's help. Changes at the cafe include a new waiter, and eventually, new ownership. Arthur’s office in Florida meets an untimely demise.