Disregarding the jokes, WA2 & Oregairu do share a lot of common points. Imperfectly humane characters, high school setting (bar the fact that WA2’s Closing Chapter, Extra, & Coda took place after high school), and a cynical take on the reality where people will naturally hurt each other, whatever choice they are going to make.
Let’s take a look at the principal characters of both. A supposedly bright, nice girl that everyone seems to love who isn’t actually all that nice inside. A frail girl with a stern, cold exterior and an issue of independence. But where Haruki comes off as an indecisive, romantically dense person who acts on impulse all the time, Hachiman has strong conviction in his ideals and is fairly aware of his surroundings (or as he puts it himself, self-aware). In the end, though, both their actions ended up hurting the people who care about them, which at one point fractured their relationship.
Whereas Oregairu is a more down-to-earth take on high school life with questions that some of us may have wanted to ask but never really say it out loud, WA2 takes its romance a step further — and with the way Haruki is, escalated to a roller-coaster ride of pain and suffering that questions the meaning of true love: is love something pure and untainted, or is it something more selfish and corrupted? Setsuna’s True End seemingly ends with everyone being happy, but one would have to wonder whether it truly embodies the spirit of WA2 — especially for the fact that Kazusa and Haruki doesn’t come up with their own solution to the problem, instead being dragged along by Setsuna’s decision. Does this sound similar with a certain scene in Oregairu Zoku episode 13? Yes.
Kazusa’s True End, on the other hand, is a pretty ugly conclusion to a beautiful tale — but it might as well be what true love means in the eyes of Haruki. In this route, a lot of characters you have come to love and care about are hurt by the consequence of Haruki’s choice; and even then, can we blame him for choosing what he had chosen? Is there even one correct choice to begin with? We never know, but certainly, getting hurt is an inevitable outcome.
Let’s remember what Hiratsuka-sensei said in volume 9 of Oregairu:
“But you have to understand, Hikigaya. You can’t avoid hurting others. People unconsciously hurt others just by being alive. Whether you’re living or dying, you’re always hurting someone. You hurt someone if you decide to get involved with them, but at the same time, you still might end up hurting someone by deciding not to get involved with them… But if it’s someone you don’t care about, you won’t even notice. What you need is awareness. It’s exactly because you care about someone that you’ll feel that you had hurt them. To cherish someone means to have the resolve to hurt them.”
It’s pretty funny how this quote resounds well with another story, but it may help us to understand what’s so compelling about these two stories in general. Both the main protagonists are deplorable human beings in their own ways. It’s not because of their writings are bad, quite the contrary; their writings are good enough to make the most deplorable humane aspect of them believable and relatable without sounding forced. And it is for that fact that in spite of the differing directions that both stories are heading toward, you can’t help but appreciate all the process, all the moments, and all the consequences.
I personally think Oregairu is headed towards a more optimistic ending. Unlike WA2, there are pivotal characters that can serve as moral compass at important times, and there is less emotional burden to resolve things romantically with more emphasis on the underlying themes of sincerity and reliance. Nevertheless, with the way Oregairu ANOTHER is ending, we might see a proper romantic resolution in the main novel.
For those of you who have only known both of these series from the anime, I recommend you to check out the original source materials since there are a lot of things you will discover that you may have not seen in the anime. You can purchase the game digitally or physically; the translation project in Baka-Tsuki is ongoing. In case you are not a fan of spending multiple hours for a visual novel, mdz provided a pretty solid summary that may come pretty close to the original experience. Oregairu’s light novel and manga series have been licensed by Yen-Press, but the fan-translation is still available online.
· MagnAvaloN · 
Yes, I can expect to see proper ending in Oregairu either (I don’t know about Wa2 very much so I will leave it at that). I think I know how Oregairu will end but I have no solid evidence so I will leave it again. But like sensei’s quote, so not try to hurt 2 girls = hurt them blindly. In other words, hurt them necessary will bring to proper/sincerity ending, or should I say, geninue ending (like Watari sensei mentioned this word before). So I can say 8man will hurt them, and I think Yui and Yukino will accept this, in order to face problems (or should I say, their relationship and Yukino’s problem involved with her sister and family).
ps. your analysis is very interesting. So I will put my own Oregairu analysis here, they focused on characters (such as Hayama, Haruno, Yukino, etc) in Oregairu LN/anime/manga, if you want to understand about them more, way to go.
please read them when not busy, and bring snack & drinks before visit this.
Feel free to, I’m welcoming fellow LN readers.
This post is more of me talking about White Album 2’s Coda endings and some similar aspects with Oregairu’s recurring theme; if you have moments to spare, you can read the summary in the link provided above.
An Oregairu Another-related post is due in a few days.
Is it me or do I see a very strong parody from oregairu?
How dare you compare those two?????