The Disappointments

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.

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  E1This Is Who We Are Now

  Mar 22, 2026· 24m

  Exciting new opportunities arise for Ray, Gary and James while Ray finds himself fixated on his ex, Dwight.

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  E2Unintended Acceleration

  Mar 29, 2026· 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.

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  E3The Donation

  Apr 5, 2026· 24m

  Ray, Gary and James go on dates.

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  E4Episode IV - A New Hope

  Apr 12, 2026· 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.

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  E5Six Minutes Forty-Nine Seconds

  Apr 19, 2026· 24m

  Ray's past comes back to haunt him.

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  E6Rabbit

  Apr 26, 2026· 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.

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  E7Chimichanga

  May 3, 2026· 30m

  James and Gary make a surprising realization. Ray puts his heart on the line.

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  E8The PigFinale

  May 10, 2026· 35m

  Ray attempts a coup at the office. James loses a client. Gary and Lorena shoot their talk show pilot.

The original webseries has been re-edited into five twenty-five minute episodes -- as they were originally intended to be seen. Now with extended scenes between Ray and Dwight restored and other fun extras. Watch The Disappointments as it was meant to be seen!

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  E1Let The Shit Show Begin

  Feb 15, 2026· 25m

  Ray, James and Gary, three close friends in their late 50s/early 60s, are rocked by the suicide of a friend from their past.

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  E2The Worst Person Ever

  Feb 22, 2026· 28m

  Ray, James and Gary deal with the fallout from a friend's suicide. Dwight offers to move in with Ray to help him pay his bills.

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  E3The Open House Thing

  Mar 1, 2026· 24m

  Dwight puts Ray on a budget. Gary, James and Ray go to an Open House.

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  E4Handling Snakes

  Mar 8, 2026· 18m

  Ray sticks up for Dwight and later learns that Keith's body is still in the morgue. James uncovers the the secret that Gary has been hiding from them all.

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  E5Love, Larceny & LossFinale

  Mar 15, 2026· 26m

  Ray, Dwight, Gary and James go to a memorial.