The Disappointments
Season 2
20268 episodes
Ray, Gary and James each find themselves with new and exciting employment possibilities that could actually turn their disappointing lives around, while also managing new challenges in their personal lives. Ray, struggling to move on after his breakup with Dwight, lands a job writing on an animated series for young girls and discovers he’s an awkward fit in a room full of Gen-Z writers. Gary finds himself hired to be the co-host of a talk show and prepares to shoot the pilot while a very unexpected relationship sprouts up in his life. And newly-licensed real estate agent James manages to find a mentor in a prestigious Beverly Hills realty firm, only for complications to arise when the two men enter into a kinky sexual affair.
Episodes
E1This Is Who We Are Now
2026-03-22 · 24m
Exciting new opportunities arise for Ray, Gary and James while Ray finds himself fixated on his ex, Dwight.
E2Unintended Acceleration
2026-03-29 · 24m
Ray's preoccupation with Dwight gets him in trouble back at the writers' room, while James takes on his first open house and gets an unlikely new real estate client. Meanwhile, Gary gets some action on his dating app.
E3The Donation
2026-04-05 · 24m
Ray, Gary and James go on dates.
E4Episode IV - A New Hope
2026-04-12 · 26m
Ray continues to be an outsider in the writers' room while Gary makes a troubling discovery about Lorena. James reluctantly allows Ray to ride along when he insists on going with James to see Phillip's house.
E5Six Minutes Forty-Nine Seconds
2026-04-19 · 24m
Ray's past comes back to haunt him.
E6Rabbit
2026-04-26 · 25m
Gary and Lorena go on a shopping spree while James deals with a complication at a client's final walk-through. Ray learns that his writing contract isn't going to be picked up and is devastated by Dwight's big news.
E7Chimichanga
2026-05-03 · 30m
James and Gary make a surprising realization. Ray puts his heart on the line.
E8The Pig
2026-05-10 · 35m
Ray attempts a coup at the office. James loses a client. Gary and Lorena shoot their talk show pilot.