The Disappointments: Season 2 (Web Series)

Season two of this comedy following three middle aged gay friends as they deal with work and love lives just dropped on their YouTube channel. There's a pretty long gap between when the seasons came out, but the story just picks right back up where it left off, and somehow the whole cast looks exactly the same, not a single visible change, which honestly is kind of wild. The first season jumped forward a year and left us knowing that Ray and Dwight aren't a couple anymore. This new batch keeps the spotlight on Ray, Gary, and James as they deal with career struggles, messy romantic situations, and figuring out what their lives even look like now that they're getting older. 8 episodes this time, each running about 25 minutes.

Ray's still not over his breakup with Dwight, and on top of that he lands a writing gig on a girls' animated show, where he's constantly trying to figure out how he fits in with a room full of much younger GenZ writers. He just can't let go of Dwight and it's clearly holding him back from moving forward. Gary meanwhile lands a co-host spot on a talk show and starts gearing up to shoot the pilot episode. Right around then he gets blindsided with news that he actually has a son from way back, meaning he's suddenly both a father and about to become a grandfather out of nowhere. It's a lot for him to process all at once, but between the career win and this family news, it ends up being a genuinely good turn in what's otherwise been a rough year for him. James, now freshly licensed as a real estate agent, gets hired and mentored at a fancy Beverly Hills brokerage by the same agent he worked with back in season one. Things get messy fast when their professional relationship turns into a sexual thing between the two of them. The younger agent keeps finding excuses to sleep with James but always dodges any real conversation about what's actually going on between them. Dwight's also back in the picture, now with a new boyfriend of his own. Since Ray hasn't moved on, we watch him spend a good chunk of time trying to make Dwight understand what went wrong, why he still has feelings for him, and whether there's any chance of getting back together. After going back and forth a bunch, we finally get the full picture of what actually broke them up, and Ray's finally able to lay it all out for Dwight.

I gotta say, this season just feels tighter and more sure of itself across pretty much every area, the writing, the production quality, the performances, even the direction. You can tell the three guys are slowly starting to realize just how underwhelming their lives have been, and we get to watch them make real headway on both the personal and professional side. The show does a solid job of pacing that growth out gradually and showing how much these three lean on each other through it all. It's not like everything wraps up perfectly career wise for any of them, but that's kind of the point, that's where the show's dark comedy comes from. It genuinely blows my mind that it's already been five years since season one, because none of these actors look like they've aged a day. I also really liked that they brought back some random side characters from the first season for quick cameos, it was a nice little detail. Honestly, within gay media as a whole, there just aren't a lot of shows or movies that focus on older members of the community, and the few that do usually don't handle it with much humor. So getting to watch familiar faces make desperate, funny attempts to fix their disappointing lives before time runs out really worked for me. I liked this season even more than the first one. (7/10)