Oregairu season 3 is not the most interesting season of the three since the main problem in the story has already been addressed in season 2.
Some people put this down to poor writing, but I honestly feel like this works out pretty well. You see this "genuine" thing has two layers to it. One is just the mutual acceptance of the nature of the feelings involved, while the other is the mutual acceptance of the severity of the feelings involved as well. The former is what the whole story was about up until the end of season 2, as Hachiman manages to embrace how he must continue to struggle and fight for proper connections with people, irrespective of his past failures with relationships. The latter is what season 3 is about. The service club members now fully embrace that they all like each other, but they are not quite ready to embrace a status quo where everyone's romantic feelings are put on the table as well.
For my review of the season itself, I'll go through the common criticisms I have seen directed towards it, and try to either defend it or agree with them. That should give you a general idea about whether you'll enjoy this season or not.
"Oregairu season 3 is nothing more than a generic love triangle"
I'd beg to differ. The way the characters have developed so far makes it a lot more interesting than just an average love triangle. One must also consider what happened at the beginning of season 2. Hayama and his clique were criticised by Hachiman & Yukino for trying too hard to protect the status quo instead of embracing and moving on with Tobe's romantic feelings being known. And now Hachiman and the service club are put into a similar situation. This is excellent, because embracing the fact that you're friends with some people is way easier than embracing the existence of romantic feelings in a small group of friends and still being able to carry on with comfort. So Hachiman criticising Hayama's clique for failing to do the latter and now finding it hard to do it himself makes him somewhat hypocritical. And that has been a theme with Hachiman's character development. He realises his hypocrisy then works on fixing it with help from the brilliant Hiratsuka-sensei.
"It is way too dragged out and overdramatic"
I do agree that it got dragged out a bit more than necessary, but not to the point where it's a huge deal for me. This was partly due to how much I love these characters, and partly due to the fact that the characters are shown to be socially inept throughout the story. Being able to express their emotions properly is not something they know much about. As a result, I'd give Oregairu the benefit of the doubt that I wouldn't give to many other shows where there is way less of a justification for why things got dragged out. As for overdramatic, these kind of shows tend to walk on a thin line between compelling display of a dramatic story, and nonsensical melodrama. How you see it would depend on how attached you are to the characters going into the third season, or what your tolerance is like when it comes to drama stories.
"The comedy is either non-existent or rather cringe"
My thoughts on Oregairu comedy are rather mixed. Anime comedy rarely makes me laugh, so things like traps, fujoshis, and chuunibyou people are rather disappointing when I see them pop up, and they're all present in Oregairu. But I still found plenty to laugh at when it came to the main characters. Hachiman's primary character arc is over, so in season 3 he comes across as a lot more chill and funnier than he was in season 2. Some of the comedy is cringe (such as a rap battle), but it's self-aware cringe rather than pretentious cringe, which can be funny for many people.
"The adaptation was too nice to Yui over Yukino"
This I completely understand. Yui moments were given a lot more importance than Yukino moments, possibly in order to create a level of balance between the two main girls. It's one thing that I did find myself feeling a tad frustrated by. This is also why I'd recommend everyone to read the LN. Hachiman's feelings towards Yukino and vice-versa are expressed a lot better over there.
Overall, it was sweet. I laughed, I smiled, and for the first time while watching a show, I cried as well. It has been well over five years of me waiting for a third season, and I am not disappointed. A lot has changed over this period of time, but my love for this series hasn't. 10/10.
