Alongside Hachiman, the two other main characters Yukino Yukinoshita and Yui Yuigahama. Yukino is the club president, and Yui joins the club shortly after requesting support from the volunteer club, when she is wanting to make cookies for her love interest.
Yukino is a cold-hearted mistress, and throughout the course of Oregairu I could never bring myself to like her. She had a cute side to her, which isn't uncommon for the stereotype she falls into, with her love for cats and cute animals in general, but this alone just isn't enough. She is a mysterious character, we don't know much about her, and never really do, and that's what irks me most about her. For a main character, she goes through a lot of development as a character, but we still know very little about her in the end. We can assume things about her, but these assumptions can neither be confirmed nor denied.
Yui, on the other-hand, is the life of the show. If it wasn't for her, it would be two gloomy characters who feel compelled to help people, just because they asked, never speaking. Through the entire show Yukino and Hachiman are rarely seen close to each other, Yui is always in the middle, closer to Yukino, but you can tell very early on that Yui has strong feelings for Hachiman. Based on the title of the anime, and the interactions between the main characters, I expected an end where Yui and Yukino would almost be fighting for Hachiman, this didn't happen, but if it did, I would have wanted Yui to win, as she was probably the strongest character of the bunch.
Let's take a look at the scores
7's across the board, after revising them twice, I think I'm sticking with that. I've already talked about the main characters, and I think overall they are worth a 7-9, fluctuating slightly between episodes, but the rest of the team drag them down.
We have Hachiman's little sister who, while cute, has some weird interaction with her brother. The "...scored high in my books" banter she has with her brother, seems very sibling like, but it doesn't seem like something I can imagine siblings saying. I have only every grown up with brothers, so I don't know if that sort of thing would happen if I has a sister a few years younger, but there was never anything like that with my brothers.
Hachiman's old school friend Yoshiteru, an annoying characters suffering from chuunibyou. He's rarely seen, and is kind of a useless character. The time wasted on him could have been spent on some of the more interesting secondary characters, such as Saika. Saika is the head of the tennis club, and befriends Hachiman quite early on. He looks a little feminine, which makes Hachiman's interactions with him a little homo-erotic at times, which makes for some funny moments, and it's a shame Hina, a big BL otaku, never ships them for her weird fantasies.
Then the final 2 notable side characters Hayato and Haruno (Yukino's older sister) just have an unpleasant aura about them. They're lively characters which I just loved to hate. I don't know what it is about them. I understand Haruno was meant to be hated, but I feel Hayato was meant to want to be hated, but actually liked.
The artwork in Oregairu isn't anything to write home about. There's nothing wrong with it, but it is quite average. I'm not going to drop it below a 7, because it had some good scenes which really help hit home the feel of the scene, but it never really managed to amaze me.
The music in Oregairu was kind of forgettable, however, the OP from season 1, and the ED from season 2 are quite catchy and very likeable. And because of these two songs, I am giving the sound a 7. The background music throughout the anime was just that, background music, I can't remember how any of it sounded, I know it was there in some scenes, but it doesn't stand out like some background music does.
If I was reviewing season 1, and nothing more, then the story would be a 9. But season 2's story arch with Iroha and the other school is just so bland. Iroha is another character I couldn't bring myself to like, but there wasn't really anything wrong with her either. I feel that too much time was spent on her, and not on progressing the story with the main characters. Sure, she was a pivotal point in Hikki and Yukino's relationship, and seeing how strong of a friendship they had... but that could have been done and over with in one, or one and a half, episodes.
Then there's the ending. I don't think it's a bad ending, it's just not an ending I enjoyed. As mentioned previously, I'd much rather have had Hikki and Yui slowly walk off into the sunset, laughing and talking, then Yui grabbing his arm in a loving way *fade to black*. But instead we get a heartfelt conversation about everyone staying friends, and no one really talking about their true feelings. It kind of feels like the ending was rushed, and they didn't really know what to do there.
As a whole, Oregairu is a great anime, it has its slow points, and it has the odd episode which you feel is just filler. But if you can look past a disappointing final few minutes of a final episode, then this is potentially an anime you'll enjoy