In this review I will talk about the whole "genuine" question and how it affected me and the whole series. So, there will certainly be spoilers, you've been warned.
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The first season of Oregairu consist in introducing all the characters and developing the relationship between them, and once this all is done, the development of the characters can begin. After only two episodes of the second season, named "Oregairu Zoku", we can already see the drama costantly increasing in the episodes. And thus, we have another type of animation, which really helps the characters and the expressions to be more emotional.

After the whole stuff about Tobe's confession, a problem that has been solved by Hachiman through sacrificing him self, Yukino and Yui got angry towards him 'cause he didn't understand something as obvious as the fact that he didn't have to sacrifice himself like that for others, because he would make the people he had next to him feel bad. Hachiman sees himself as a lonely person, and never realizes that he has people next to him, so he never even considered the idea that the club could be made up of people who cared about him. After that scene, Yukino and Yui got angry because he had once again sacrificed himself without thinking about the feelings of the people he had next to him.
In fact, in Oregairu the main character, Hachiman Hikigaya, is a lonely person who has never really wanted anything in life, he just wanted to be alone and to live life alone without being particularly involved in situations, consequently, appreciating himself for what he was -or rather, for what he saw about him. When he began to meet people, being forced to attend them, he established a certain friendship with the so-called "volunteer club", which aims to help other people solve problems. To solve these problems, the protagonist Hachiman uses methods that lead him to lie, so after some time, when even his clubmates (with whom he had already established a relationship that he, a loner wanted as well) pointed this out to him, he began to hate himself for lying, which had never happened in his life. After a while, he takes his courage and communicates to the club his feelings about him, saying one of the most famous quotes in Oregairu, "I want something real".
By now, his relationship had become something that he never had in his whole life and yet he didn't want to see, he pretended not to see, surrounding himself by a cynical and hypocritical wall of empty words. In fact the scene in which he desires something genuine is so touching because he's admitting that he no longer wants to lie to himself or others and find a real relationship where he can talk openly without lying.
That's the moment he realizes he is a liar, that he wants a friendship, but that he has been scared in the past because the past has only made him see him being constantly rejected and neglected by people. Even when he says the quote “If to be truthful is to be cruel, then lying must surely be an act of kindness. And so, kindness is a lie, and I hate good girls.” he is lying to himself because he is scared that he might attack or that he can feel affection for someone who is kind to him. Everything Hachiman has been in the whole series has been a lie, to hide what he feared... even though he says he hates people who wear a mask, he used one himself too. We see the "real Hachiman" only after that "genuine" speech.

Now, why all of this has touched me deeply? The time I watched this anime was in a dark period of my life. To clarify, I was fourteen, and most of my relationships were created and based on false beliefs, false opinions, and consequently, false friends full of lies. Watching Oregairu touched me due this reason, and seeing how an edgy character like Hachiman managed to change and find something that managed to change it, made me want to become a real person myself. This anime changed me and my life, for a simple reason: after seeing it, I discovered a new side of human relationships, and although it may seem like a basilar thing to many people, it really touched me, helping me to become a better person. I'm so grateful to Watarin to have written such a series.
Now leaving that aside, I want to talk about why Hachiman is such a beautiful character. The first season is composed of him dealing with the outside world. To clarify, I find that season one, despite seeing Hachiman as a liar and hypocritical character, is an amazing and well written repertoire of philosophy that the author Wataru Watari built and embellished by showing us his knowledge. I mean, I think it can easily be adapted into everyday life. That's what makes what Hachiman says so beautiful. Although he is lying to himself and is an hypocrite, what he says is true, and he is unaware that he is also lying to himself, hiding what he really wants. His character develops in such a perfect way that I think it is legitimate to give him the title of one of the best-written protagonists in anime.
In the end, I find that this anime is very well directed, accompanied by the perfect ost for the situations, by a fantastic dub, and by the animations that express at their best what Watarin wanted to communicate with his light novel.
TL;DR, if you came here to see my score then you're a dumb, because this review is a pure analysis about Hachiman's character, and you have to read it. Anyway, I will leave you with this quote:
Hard work betrays none, but dreams betray many.