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Dated 4 August 2020: The End of Oregairu ~Air/My Purest Heart for Thee~

Yukino
I wonder if sales of blue-blocking computer glasses are down
now that you can just enable night mode on basically any OS.

I gave Oregairu a second chance in anticipation of Yahari Ore no Seishun Love Comedy wa Machigatteiru. Kan (My Teen Romantic Comedy SNAFU Climax!) completing the series this season. I'm glad this worked out a lot better this time than when I watched Shakugan no Shana II so I could watch Shakugan no Shana III. (Shana II is not great.) Through four episodes, the conclusion of Oregairu III contains the sort of emotional resonance you ought to expect by now if you've been following the previous seasons.

Yui and Hikigaya
Kids and their selfies.

It's a difficult balancing act, to be sure, capturing the stakes in a way that makes us care about the outcome without swinging too far into melodrama. Still, I'm only about 80-percent sure that this season will cover the source material's conclusion. I mean, I have at least heard that this is the case. But not having read the light novels, I'm a little unsure how the series will manage to wrap things up within the remaining episodes. My guess is that some characters just won't get covered to the satisfaction of their more ardent fans.

Dated 29 September 2020: The End of Oregairu ~Air/My Purest Yahallo for Thee~

Iroha
BEST GIRL.

Yahari Ore no Seishun Love Comedy wa Machigatteiru. Kan (My Teen Romantic Comedy SNAFU Climax!, among other localized names) completed the three-season run of a harem comedy that fared surprisingly well despite my initial misgivings. Generally speaking, the term "harem comedy" itself feels anachronistic now and less appropriate even when applied to shows such as Gotoubun no Hanayome (The Quintessential Quintuplets) compared to the label's Love Hina-era association (at least in my mind). I suppose it's probably still applicable for shows such as Kanojo, Okarishimasu (Rent-a-Girlfriend). But I digress.

Yui
Oregairu might have been a better series if told from Yui's point of view.

These types of shows invoke a competitive element that pits various female protagonists against each other to vie for the male lead's affection, ultimately "winning" by becoming the romantic interest he selects at the conclusion of the series. Longtime readers of this blog may remember I'm not a fan of this construct when the male lead is so frequently a dull sap, to say nothing of the ones who are legitimately terrible cretins. I'm did not watch Kanojo, Okarishimasu, but I did watch it get shredded on the Twitter, and Potato-kun appears to be a colossal douche in addition to the show's numerous other problems. Does the girl who ultimately ends up with such a character really win? [Spoilers: No.]

Hachiman and Yukino
Kids and their selfies.

Oregairu does not suffer from this particular problem, at least by its conclusion. Hachiman in the third season is no longer the same person he was in the first season. Unfortunately, the girl who ultimately "wins" has her own issues. [Spoilers henceforth, obviously, if you haven't already either seen this coming or learned about it via some other way, such as discussions about the light novels' ending.]

Komachi and Iroha
It's about the future, Madam Chancellor.

Yukino is not interesting. She is supposed to be the most complex of the various love interests, and has some significant hang-ups that admittedly align well with Hachiman's character, but I never found her problems or growth compelling. As far as "winning" the harem comedy contest goes, she is the most sensible one to pair with Hachiman, but my lack of investment in their relationship makes the show's resolution somewhat hollow. Ultimately, it was still a good journey, and I can appreciate why Oregairu accumulated so much praise during its run, but I can't quite point to it as a much-watch show by any means.