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I think I understand what people mean by now when they say "it went on for too long". Now granted, no piece of art could be made better by simply changing the duration, but Oregairu's flaw in my opinion is that while the individual arcs and the characters inside of them are engaging and interesting, the overall story and the major relationships which are developed are largely disappointing.

Part of this I think is because instead of a story, there's a painful will they won't they component to everyone's behavior. At first this provides a counterpoint to characters such as Hayama's good-natured demeanor and Hikigaya's ... strong will, and overall I found no problem with how this was all handled in season 1.

From season 2 on however, most of the characters end up "Flanderized", for lack of a better word. I think this is because, while the show presents a lot of interesting conceits around conflicts and social awkwardness, the actual relationships that the show is built on come off very unnaturally and lack charisma. In particular the dialogue, though I don't know how well it was translated on the site where I watched the show, was painfully cryptic at times for no good reason. There is a lot of dialogue on the show that I enjoyed, but after a while, listening to the ins and outs of characters whose next actions I've lost interest in is just painful.

Overall, it's worth watching if you're interested in this cynical type of character, I myself related to him in a lot of ways. The charming thing about it is that it depicts a character who is cynical towards relationships but also wants to be involved.

Do you ever want to not try things? Is forming a structuralist perspective on reality too boring? Why does my pee pee come out yellow? This anime is like if Sayonara Zetsubou Sensei went on a lunch break. Very digestable series at 3 minutes an episode, 50 seconds of which can be skipped because I could sing and draw a better opening if you gave me 50 minutes. The entire opening has 8 lyrics which convey less than no meaning, and it trumps up the literally non-existent action "element" of the series. So anyway the 2 minutes and 10 seconds that is left are surrealist ... commentaries on the already ridiculously portrayed premise, much of the time through non-sequitur and all in a way that shows little respect for the idea that the show is supposed to be a comedy. The show doesn't waste it's own time, it's not down for anything, but neither does it waste your time. Basically the key to enjoying this is deciding the stupidity and the surrealism mix and if they don't that's good for you