

(Before I start, I implore you to watch the Season 1 specials before starting this season if you didn’t already. Certain events at the beginning of this season will not make sense if you don’t watch them first! Also, watch the specials, even if they hurt to watch!)

If you made it this far, congratulations, you’re about to go through the ride of a lifetime! Not to be outdone by season one, this season only ups the ante and doubles down on what made it stand out in the first season.
There are slight differences with this season, with A-1 Pictures being the studio that made this season (AIC Studio made the first season). There isn’t much difference in animation quality between both seasons, with character designs staying the same and animation improving somewhat. The only big difference between both seasons production-wise is that this season has fewer arcs and more standalone episodes.
This season focuses more on Kyousuke himself, while the first season focused more Kyousuke helping Kirino. After getting her to come back to Japan, Kirino still acts as similar as to she did in the first season but has more ‘dere’ moments. Kyousuke has more interaction with Kirino’s friends, Ayase, and Kuroneko in particular. Characters like Kanako and Saori, who didn’t get much air-time in the first season, get more time this season, although still not that much.

The best thing about Oreimo and one of the main reasons that it’s so gripping is its characters. The second season tries to develop side characters more, Side characters that would normally not get much air-time, like Ayase or Saori, each gets an episode dedicated to them. They’re both great characters, so it’s awesome to see them both get their own episode. As good as that is, it does sacrifice from the actual plot, which was more erratic this season.
While the first season was a more one-to-one adaption of the light novels it was based on, this season cuts way more source material and is selective in what it adapts. While there are external circumstances for why the studio decided to go this way, I still have to judge this season as it is presented. The last half of the anime was rushed, even skipping most of a full volume of the light novel. The result is that we end up seeing major plot events sneak up to us, without little preparation or context for why it’s happening. This is the case especially with Minami, whose childhood arc with Kyousuke was for the most part cut, which in turn makes her less likable in the anime.

For a typical anime, this would be an instant turn-off, but for an anime like Oreimo, there is almost a bitter-sweetness to witnessing this. It creates a whole new monster from what it intended to be. It taunts the viewer, hurting its feelings and punishing them for being emotionally invested into certain characters. Its effacement causes the viewers to fill in the gaps for what they didn’t see, and then get upset about it. Oreimo is the only anime that I’ve seen do that. I won’t give points for it, but Oreimo is one of the most memorable anime that I have ever watched, for this reason among others.
(The good thing for us is that the Light Novel fills in those gaps. They’re all translated into English, so you can find them and download the PDFs online if you’re interested.)
Oreimo is a one of a kind anime. I will never forget it as long as I live. Hell, this is my fifth time re-watching it, if that gives you any idea how insanely memorable it is. Does that make it a good anime though? Not really. While making it memorable, the rushed pacing of the second half of this season creates unnecessary drama and makes certain parts forgettable. The first quarter, while having a few good episodes, is totally bland compared to the second half, and doesn’t progress the anime that far.

Even if it isn’t that good, and the plot of the anime is unapproachable to many (for good reason), I think everyone should watch Oreimo at least once. It is an emotional journey that will leave you empty as a whole, wondering what you are doing with life. It may make you take up smoking cigarettes as a hobby, but I think it’s worth it.
As the late Jim Valvano said, “If you laugh, you think, and you cry, that's a full day. That's a heck of a day. You do that seven days a week, you're going to have something special.” Oreimo will make you do all three. It’s hard to explain my affinity for it, especially since I’m not into other anime of the same nature. Oreimo has something special about it, it just is in a league of its own. Even if the score I give it is mediocre, and if its contents are disgusting, and if it’s a rushed product, I would recommend it.

(If you’re looking into the meaning of the ending of the anime, I would recommend you to google it. The Oreimo subreddit explains a lot about it and clears things up. Also, read the Light Novels if you’re that interested.)
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