Synopsis
Three gay men navigate middle age, its trials and triumphs. After the death of a close friend, they must support each other as they examine the idea that maybe things didn't work out exactly as planned.
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Cast
Seasons
Season 1 (Director's Cut)
5 eps · 2026-02-15
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!
Season 2
8 eps · 2026-03-22
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.
The Disappointments airing schedule, episode calendar, cast, and synopsis. The Disappointments airs on .