The biggest main reason has solely to do with what I generally look for when I watch anime or read light novels. Character development. The second biggest thing I look for is complex dynamics between characters, and OH BOY do we get some very complex character dynamics in Oregairu. Watari is phenomenal at building a character in this series, because even the smallest of side characters get a personality that is not only believable, but also relatable as an audience member to varying degrees. The anime, and especially Studio Feel's adaptation of the center volumes of the LN, is no different in this approach. There are things that you will miss of course, but as a LN adaptation Studio Feel hit the nail on the head.
The story has quite a dramatic shift from the first season, which was done by Brain's Base and actually does a wonderful job of properly introducing the characters while giving us plenty of comedic relief. Think of it as practice exams before the real deal, because the culture festival arc turns the drama up to 10 and we shift into the heavier moments of Oregairu once 8man antagonizes the culture festival leader. If Season 1 was meant to introduce the struggles that Hachiman faces, then season 2 begins to delve into the darker parts of these struggles and the sources that lie underneath the facade that even Hachiman has yet to recognize.
Youth is a constant struggle, Hachiman recognizes this. The series has yet to truly become a romantic comedy. Sure, there is definitely chemistry between Hachiman and the cast, but this is not the true beauty to this series. No, that lies in the dismantling of a cynical outlook on life that each of the main characters carry on their shoulders. We see Hachiman burning through his emotional capabilities to help people out of a partially narcissistic place, thinking he's the only one lowly enough to break for someone else's gain, and partially out of a lack of true self-worth. He would like nothing more than to be a corporate wage slave, but he also aspires to be a model house husband. These come off as jokes, but Hachiman does not truly believe he is capable of anything greater.
The depth of the characters, their pitfalls, their suffering, their angst, it can get gritty and frustrating and this season really pushes the drama further. The darker tones and the sullen moments are balanced by some of the most beautiful, poetic moments I have seen in anime. One example that strikes me every time I watch is when Iroha is carrying her bags from the convenience store and Hachiman offers to carry them as he usually does. She says she can handle it, and then begins to hobble across the sidewalk. This scene plays out very slowly, but as you watch their silhouettes cross the road in the orange light of a horizon-bound sun, Hachiman slowly grabs the bags from Iroha's side opposite of him. It captures the bond that he formed with someone he would never have anything to do with and the amount he truly cares for them. The moments with Iroha are special because they reveal a deep change within Hachiman. Everyone provides a catalyst for this change.
We see Yukino and Yui both go through their own struggles. They both get set aside by Hachiman unbeknownst, or at least unintended, by him. They're bonds are tested and of course Hiratsuka-sensei is always keeping an eye out for her favorite students. The dynamics are just so well-rounded and they help make the characters more believable.
The art is vastly improved from Brain's Base season one. We get to see Hachiman looking a little more like a human being and his hair is a lot less green. We get to see Yukino look a lot less harsh and Yui a lot more girlish. Hiratsuka-sensei loses some of the tomboyishness that the first season actually nailed pretty well, but that's alright because the pretty boy, Yamato, who looked a little more jocular than preppy in the first season got proper refinement. For some reason, Komachi and Totsuka don't seem to change all that much, they were at peak cuteness for both seasons I suppose. The settings and the expressions are deeper and more emotional. Yui tearing up during the school president election arc, Hachiman and his genuine moment, Yukino with the smile of sadness through half the season. The anger, the passion, the fear and sadness, the happy moments, the goofy scenes. Everything is well-paced and well-placed.
The sound, specifically the voice acting, is wonderful. For both the sub and the more recent dub, both have a great cast that shine. The soundtrack borrows some from season one, but there are plenty of new songs that capture the moments well.
I will praise this anime until the cows come home because it is an exceptional example of the rom-com genre. It proves that romantic comedy doesn't always need to be romantic and doesn't always need to be funny. Comedy without a little bit of tragedy is tasteless. Romance without non-romantic relationship building is overplayed. Oregairu is not going to hold your hand or give you the fan service you desire, but it will give you plenty of wonderful characters whose quirks may drive you up a wall but their good moments are heartwarming and their bad moments can be absolutely heart-rending. This season of Oregairu gets to be called a masterpiece in my humble opinion, because it adapts the light novels in a way that stays relatively true to the nature of the source material. It is capable of capturing a respectable amount of the depth you would get reading this series. I want to go back and read the whole LN series again...
