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I personally believe that this is a series where you need to have experience before completely enjoying it. Experience of what, you may ask? The experience of being the same as MC (exclude the rom-com factors.) And I am talking about just the MC as a whole. No other character. Not at all.

When something is relatable or referencing to you in a positive sense, there is automatically a smile on your face subconsciously. It's the same as when your workplace or your hometown is mentioned in a foreign discussion. In the same manner, when you feel like you can see yourself, your past/present as ... a character on the screen, it automatically makes you more attracted towards it. Having a pessimistic outlook on things, self consciousness, social anxiety, all these conditions merely formed due to unpleasant past experiences, i guess everyone who freaking love these series can relate to this. I am sure. Why you ask? Because this series is so written and presented that certain things will be understood without even mentioning in words and only those who have experienced such a thing can actually grasp the full of this series. Source : Me

It's the same as "Only after being fat, you can actually experience what it means to be fat if you are too self-conscious." One of such experiences in the series is how Hachiman bends while walking with his hand always in his trouser side pockets like he finds peace in that. This is one of those which is very relatable for me, for you maybe and for the writer in particular because it's like Oregairu understands every aspect of what it means to be an extremely self-conscious person (i am not talking about being a loner). So the conclusion of this whole thing is that no matter how much time you spend reading analysis, blogs regarding season 2 in particular, you will never be able to understand it because you can't understand science just from theories.

Besides all this, what do you think might be the reason that many people are drawn away from the series at certain points in season 2 in particular? It's simple. Read the title "My Youth Romantic Comedy is Wrong As I Expected". Who is 'my here? Hachiman Hikigaya. We are only seeing things through his perspective. That's why we can understand him a lot better than any other character in the whole series because we are literally getting enlightened by his inner monologues. The other characters are too complex for even Hachiman to understand perfectly so how are we going to? If Oregairu had been made such a way that Yukinoshita were the MC, do you think you can ever understand Hachiman? No. You can only make assumptions on what you interpret. Even i can't understand other characters that much and merely form my assumptions about that character in particular.

That's why the inexperienced find it difficult to get attached to this anime because the main reason why I, why many love this anime is because how Hachiman Hikigaya's character is sketched. If you entirely remove this concept & attitude from the anime, you will find melodrama for sure.

-thank you!