The Disappointments: Season 2 (Web Series)

The second season of this comedy about three middle aged gay friends juggling work and love has finally landed on their YouTube channel. There was a pretty sizable wait between seasons, but the story resumes exactly where it stopped—and somehow the entire cast looks precisely the same, without a single visible change, which is honestly kind of wild. Season one skipped ahead a year and left us with the knowledge that Ray and Dwight were no longer together. This time around, the focus stays on Ray, Gary, and James as they navigate career problems, complicated romantic lives, and the question of what their futures are supposed to look like now that they’re getting older. There are 8 episodes this season, each about 25 minutes long.

Ray still hasn’t gotten past his breakup with Dwight, and then he picks up a writing job on a girls’ animated show, where he has to work out how he belongs in a room packed with much younger GenZ writers. He can’t seem to release his grip on Dwight, and it’s obvious that keeping hold of the past is stopping him from moving on. Gary, meanwhile, gets a co-host position on a talk show and begins preparing to film the pilot. Around the same time, he’s hit with the news that he has a son from years ago, which means he suddenly becomes both a father and an unexpected future grandfather. That’s a lot to absorb at once, but with the career opportunity and the family revelation happening together, it winds up being a genuinely positive shift during what has otherwise been a difficult year for him. James, newly licensed as a real estate agent, finds work and a mentor at an upscale Beverly Hills brokerage with the same agent he worked for in season one. Their professional arrangement quickly gets complicated when it becomes sexual. The younger agent keeps inventing reasons to sleep with James, while avoiding any honest discussion about what their relationship actually is. Dwight returns to the story too, now with a boyfriend of his own. Because Ray still hasn’t moved on, we spend a good deal of time watching him try to get Dwight to understand what went wrong, why he continues to have feelings for him, and whether they might still have a chance of getting back together. After all the back-and-forth, we finally learn the full story behind their breakup, and Ray is at last able to tell Dwight everything.

I have to say, this season feels sharper and more confident in just about every department: the writing, production quality, performances, and even the direction. You can see the three men gradually recognizing how disappointing their lives have been, while also watching them make real progress personally and professionally. The show takes its time with that development and does a good job showing how much the three of them depend on one another along the way. None of their careers end up neatly resolved, but that’s really the point—and it’s where the show’s dark comedy comes from. I honestly can’t believe it’s already been five years since season one, because not one of these actors looks even a day older. I also enjoyed seeing a few random supporting characters from the first season return for brief cameos; it was a nice little touch. When it comes to gay media in general, there really aren’t many shows or movies centered on older members of the community, and the handful that do exist usually don’t treat the subject with much humor. So watching familiar faces make desperate, funny attempts to repair their disappointing lives before time runs out worked very well for me. I liked this season even more than the first one. (7/10)