First, make sure you've watched all the ONAs, which are not on Crunchyroll or Funimation. The ONAs are crucial for the development of the series and missing them is oftenly the main cause of confusion among fans. The ONAs are:
Kyousuke and Kirino are essentially confirmed to still be together after the ending.
At the end of the last episode Kyousuke mentions the one wish he won from Kirino and kisses her on the cheek. The light novel does not specify a cheek kiss and is implied to be on the mouth. Furthermore, the wish is phrased as Kirino “doing one thing he asks”, which an unexpected kiss is not. Kirino says they will have more life-counselling, which had always been an attempt to bring them closer together. Narratively, if he wasted his one wish on just a cheek kiss, it would be an almost completely irrelevant plot point for the author to include. Kyousuke's true wish is thus almost certainly to break their earlier promise and go back to secretly dating.
The author interviews strongly imply this. In them, Fushimi complains about the publisher, and he says about the ending:
...if I were to add my own redundant comments for those who want to re-read it, I would say: A Complete Kirino Ending. Just like the Life Consultations that started it all, the story ends with the siblings having a shared secret.
The canon short story "A Momentary Chance Encounter" says:
[Kuroneko says:] “All the women who dare to brag about their love life before me are bitches, all right?”
[Kirino says:] “Wait! I haven't be, be, be, be, been bragging at all, you hear!”
“Yes, you have. Why, specifically speaking, that Sunday last week----...”
And right there, suddenly, Kirino with her face completely red, glares at me, and shouts out in a really loud voice. “I haven't been bragging at all, okay!”
...I get it already, just stop making a scene in the bookstore, all right.
(Baka-Tsuki trans.)
Kirino and Sagiri in the Eromanga-sensei light novel
Since Kirino's trying to justify herself to Kyousuke, it seems pretty clear that she has actually been bragging about their relationship to Kuroneko. Finally, in Eromanga Sensei Vol 11, which takes place some time after "A Momentary Chance Encounter", Kirino talks to another character and implies that she still thinks of herself as Kyousuke's wife and indicates she is now cooking for him:
Kiririn: Yeah, that’s right. You’re living together, yeah? Then why don’t you do the housework well? Why don’t you become the perfect sister and wife? In my experience, I think it’s quite effective...Hand-made dishes—I think they should help a lot. Bento and bagged sweets.
(Oracle Dutchess trans., V11, Ch3)
"I Want More OreImo"[]
Anime[]
Saori and Daisuke in the DVD/BD specials
The OreImo Season 1 Character Commentaries include the characters making comments on the episodes as well as generally chatting with each other.
The OreImo Season 2 Shorts are mostly character previews as well as animations of some light novel plots like Kyousuke and Akagi going to an adult store. However, there are some original stories like Kanako talking with Kanata about Maschera as well as Kyousuke and Kirino playing an MMORPG together.
The OreImo Bluray Disc movie, with a translation by Dizzy Ziddy, involves a shrine visit as well as Sakurai, a character who is in the light novels but not the anime.
The OreImo x Eromanga Sensei crossover, with a translation by Dizzy Ziddy, involves Sagiri drawing Ayase, Kuroneko, and Kirino.
Literature[]
The light novels are the source for the anime, with Volume 11 in particular having an important plot that is not in the anime. The NanoDesu translations are better but only went up to Vol 6, after which Baka-Tsuki's are the only option.
Important Stories
A Momentary Chance Encounter was partly animated in Eromanga Sensei Episode 11
"A Momentary Chance Encounter" happens half a year after the epilogue and involves the OreImo cast meeting in Akihabara, as well as tying into Eromanga Sensei.
"Ten Year Reunion" includes Kirino watching the last Meruru episode, as well as an epilogue happening ten years after the series.
Probably Canon
"House-Sitting in a Thunderstorm" takes place a month before the series when Kyousuke's and Kirino's relationship is still terrible.
"I Can't Possibly Ask for Life Counselling from My Brother" is Kirino's perspective of the first episode's events.
"Memories of a Fallen Angel" is Kuroneko's perspective of the second episode's events.
The Drama CD Short Story Booklet includes Kirino meeting the owner of the maid cafe, baking Valentine's chocolates, and getting addicted to Love Touch (the last of which is in the anime).
Probably Non-Canon:
"Lowered Voting Age pamphlet" is a short story released when the voting was lowered from 20 to 18. To help get out the word and combat widespread voter apathy among the young. It was done in collaboration with the Japanese Ministry of Internal Affairs and Communications.
The "Learn English with OreImo" book is written in Traditional Chinese, probably released in Taiwan or Hong Kong.
Non-Canon[]
The "IF Series" are alternate route light novels for Ayase, Kuroneko, and Kanako.
"There's No Way My Black Haired Little Sister is This Cute" is an alternate universe story where Kyousuke and Kirino never grew apart.
"An Ending's Continuation" is a dream Kyousuke has during the PSP game about his future wife.
There are two crossovers with "A Certain Magical Index", which are "A Certain Clubroom's Fanatic" involving the game club and "A Certain Collaboration" where they meet Misaka Mikoto.
Manga[]
The covers for the Oreimo and Orekou manga
The OreImo manga only finished adapting Episodes 1 to 5 of the first season.
"Ore no Kouhai" focused on Kuroneko as well as an alternate route for her.
"Ayase IF" is a manga adaptation focusing on an alternate Ayase route.
"Kuroneko IF" is a manga adaptation focusing on an alternate Kuroneko route.
Audio[]
The Drama CD has Kirino talking to Kuroneko after returning to Japan, with a summary here.
The Drama CD has Love Touch 2 coming out, and Kirino asking Ayase to help cheer up Kyousuke.
The Drama CD has Kyousuke meeting Kanata again before the last episode.
The Radio Show was a promotion for the anime and involved Kirino's and Kuroneko's voice actresses chatting, sometimes in character.
Saori in the PSP visual novel's main menu.
Games[]
The OreImo PSP visual novels have routes for nearly all the girls and are being translated by Dizzy Ziddy.
OreImo Happy enD is a Playstation 3 game with some Youtube translations by Dizzy Ziddy.
"I Want More Things Like OreImo"[]
Eromanga Sensei by Tsukasa Fushimi and Kanzaki Hiro
By Tsukasa Fushimi[]
"Eromanga Sensei" is the author's main other work and is very much a spiritual successor, also involving a tsundere otaku sister. It is even set in the same universe, with some OreImo characters having cameos. It has a light novel, manga, and anime, as well as associated spinoffs.
"The Thirteenth Alice" and "Neko Sis" are light novels by the same author but are so far only available in Japanese.
Similar Anime[]
"Toradora", about a guy dealing with a violent girl. Taiga is quite similar to Kirino, both are Tsunderes even though Taiga is more violent. The male MC is also helping Taiga a lot like Kyousuke does for Kirino.
"Boku wa Tomodachi ga Sukunai (Haganai)", about a guy trying to make friends. He makes a club with a tsundere obsessed with galge/eroge and little sister, a mad scientist glasses fujoshi, among others.
"A Sister's All You Need", about a guy who writes little sister novels for a living. He even keeps figurines of Kirino and rants about how great the OreImo anime is.
"Saekano: How to Raise a Boring Girlfriend", about a guy making an imouto VN who recruits help from an otaku tsundere, a dark-haired pseudo-yandere, and his overly-friendly cousin.
“Himouto! Umaru-Chan”, about a guy dealing with his annoying younger sister who is outwardly high-achieving but secretly an otaku.
"Domestic Girlfriend", about a guy whose father remarries, so he finds that his new stepsisters are the teacher he has a crush on as well as a random girl he already slept with.
"Oniichan wa Oshimai!", about an overachieving imouto that ends up making her older brother feel inadequate.
"Imōto Sae Ireba Ii", a love letter to the imouto genre with references to real series (even Kirino gets referenced).
"Jaku-Chara Tomozaki-kun" about a guy coming out of his shell because of the main girl getting him to do things with her. The main girl is likewise a smart, popular track athlete with a secret hobby.
Honorable mentions/Often recommended:
Mamahaha no Tsurego ga Motokano datta
B Gata H Kei
Watashi ga Motenai no wa Dou Kangaetemo Omaera ga Warui! (Watamote)
Nogizaka Haruka no Himitsu
The World God Only Knows
Lucky Star
NHK ni Youkoso!
Yuru Yuri
Nisekoi
Yahari Ore no Seishun Love Comedy wa Machigatteiru (Oregairu)
Hentai Ouji to Warawanai Neko
Suzumiya Haruhi no Yuutsu
Chuunibyou demo Koi ga Shitai
Mayo Chiki!
Ore no Kanojo to Osananajimi ga Shuraba Sugiru
MM!
Yosuga no Sora
Kiss x Sis
Koi Kaze
Oniichan no Koto Nanka Zenzen Suki Janain Dakara ne!!
Oneechan ga Kita
Oniichan dakedo Ai Sae Areba Kankeinai yo ne!
Candy Boy: Nonchalant Talk of the Certain Twin Sisters in Daily Life
.png){kind=link}
