Characters in the series include, but are not limited to:
- Kyōsuke Kōsaka (高坂 京介, Kōsaka Kyōsuke?)
- Voiced by: Yuichi Nakamura
- Kyōsuke is the 17-year-old main character of Oreimo. He has a distant relationship with his sister, feeling that this will never change. However, this suddenly changes when he finds one of her adult games and learns that she is an otaku. Through this, he tries to be a supportive older brother while realizing he himself knew very little about his sister, such as being almost flawless at school to working as a model. Later on he takes up more of his role as an older brother to her, and appears to be able to tell what she is thinking or really meaning to say despite her tsundere personality. Despite this, she is generally the dominant person in their relationship, with Kyōsuke being shown to be openly intimidated by her, only standing up to her in truly serious situations. Kyōsuke prefers to have a relatively peaceful and simple life despite the fact that the drama Kirino brings makes his life anything but peaceful. He also seems to enjoy drinking tea from a carton as he frequently has a glass of it when he gets home.
- Kirino Kōsaka (高坂 桐乃, Kōsaka Kirino?)
- Voiced by: Ayana Taketatsu
- Kirino is Kyōsuke's 14-year-old younger sister. She is mature for her age with a cold, tsundere-like personality. She has a strong "little sister" fetish and owns many adult games with older brother/little sister themes, which she got a job modeling to pay for. Despite this, she states she does not know why she started liking it, though it is suggested that she has a brother complex and is using the games as a surrogate to this. She often denies such feelings and believes the 2D and 3D worlds should be kept separate. Nevertheless, she is shown to be very frustrated when he is with, or shows interest, in other girls such as Manami who she accuses as being "all over" Kyōsuke. Likewise, she frequently forces Kyōsuke to spend time with her, whether it is playing games or taking her out, but denies that she actually enjoys the time they spend together, even going as far as hitting him after he complained that she was ordering him around as if he was her boyfriend. Despite stating she only likes her Eroge because of the cuteness, she shows a disturbingly perverted side to herself when playing. She uses the screen name Kiririn when with her otaku friends.
- Daisuke Kōsaka (高坂 大介, K'ōsaka Daisuke)
- Voiced by: Fumihiko Tachiki
- He is Kirino and Kyōsuke's domineering father. He is a high ranking officer in the police and has a no-nonsense policy at home. He does not like the fact that Kirino is a model, but allows her to do so if she does well in school. He is severely against otaku, believing them to be a waste of a life, so when he finds out Kirino is one, he orders her to throw away everything otaku-related in her room. He can be quite abusive, as when Kyōsuke once stands up to him, he thrusts his son into a submission hold where his grip is so hard it leaves a bruise. It is shown he truly does care for Kirino despite his gruff exterior, as he owns every article and picture of all her accomplishments.
- Yoshino Kōsaka (高坂 佳乃, K'ōsaka Yoshino)
- Voiced by: Akeno Watanabe
- She is Kirino and Kyōsuke's loving mother. She is aware of her daughter's obsession, as she has referred to her as "my otaku daughter".
- Manami Tamura (田村 麻奈実, Tamura Manami?)
- Voiced by: Satomi Satō
- Manami is Kyōsuke's childhood friend who wears glasses. She is described as 'plain'. She has a crush on Kyōsuke and blushes to his compliments. She becomes comically blind when she is not wearing her glasses and seems to sprout dog ears when complimented.
- Iwao Tamura (田村 いわお, Tamura Iwao?)
- Iwao is Manami's younger brother. He seems to have a facisnation with Western influences such as his fascination concerning the Skinhead subculture and rock.
- Saori Makashima (槇島 沙織, Makashima Saori?) / Saori Bajiina (沙織・バジーナ, Saori Bajīna)
- Voiced by: Hitomi Nabatame
- Saori is the leader of the "Anime Girls Unite!" group on the Internet, whom Kirino meets in a meet-up. She wears very thick glasses (shown as swirls) and speaks with an exaggerated tone. She is a fan of Gundam and is also a collector of their model kits. Saori is an aristocrat from a wealthy family, and speaks with a highly formal voice outside of meeting with her friends. She is tall and usually has to get cosplay tailor made. As Kyōsuke says, Saori is drastically different from how she communicates through the Internet and through phone or speaking with her in person, to which she seemingly switches to a refined and sophisticated persona. According to Kyōsuke in the light novels, she is dressed as a typical otaku from television but has the body of a supermodel. Despite being a middle school girl around Kirino and Kuroneko's ages, she is around the same height as Kyōsuke, which surprises him when he first meets her. Despite her cheery attitude, Saori is quite lonely, living by herself, and has always feared that one day her true friends (Kirino, Kyōsuke, and Ruri) would leave her in a similar way that her older sister (who got married and moved away) left her.
- Ruri Gokou (五更 瑠璃, Gokou Ruri?) / Kuroneko (黒猫?)
- Voiced by: Kana Hanazawa
- Ruri is another otaku girl who lives near Kirino and often wears gothic lolita clothing based on a character from her favorite anime, even during hot weather, and will sometimes add cat ears and a tail. Due to both of their tsundere-type personalities, she constantly clashes with Kirino when it comes to anything. However, Kuroneko does care for Kirino. Unlike Kirino who likes little sister-themed games, Kuroneko enjoys teen-centered fantasy anime. She often mentions "dark magic", claiming that she has it, usually to Kirino or to Kyōsuke. She is noted to have an eloquent manner of speaking and a very large vocabulary and, to where Kirino commented she needed to use a dictionary to translate her novel. This seems to derive from her favorite anime. Kuroneko actually wears red contact lenses to make her bluish eyes seem red. Kuroneko also has younger sisters, whom she dearly cares for, though her sisters and mother both seem to worry about Ruri when she in her otaku mode. At school, Kuroneko wears normal clothes and at home, takes care of her younger sisters. In the anime, she later refers to Kyōsuke as "Nii-san" due to her wishing to have an older brother and suggesting to annoy Kirino while hinting some affection towards him. Kuroneko is quite short, coming only up to Kyōsuke's shoulders and is shorter than Kirino. Kuroneko later becomes Kyōsuke's girlfriend.
- Ayase Aragaki (新垣 あやせ, Aragaki Ayase? )
- Voiced by: Hayami
- Ayase is Kirino's friend and classmate who works as a model alongside her and is also her best friend. Ayase is a friendly, nice, and refined lady, but becomes agitated and somewhat violent at the thought that she is being lied to, which she hates above all else. She tends to believe what she sees on the news. Therefore, she disapproves of anime and manga, calling it a disgusting hobby, especially adult games, due to the media portrayal that otaku will eventually become criminals.
- Kanako Kurusu (来栖 加奈子Kurusu Kanako? )
- Voiced by: Yukari Tamura
- Kanako is Kirino and Ayase's fellow friend, classmate and model, who sometimes swaps between a cute personality to a bratty one. She is a talented singer who dreams of becoming an idol, often going to a lot of auditions. Since she goes to karaoke places frequently, she is capable of remembering any song she has heard at least once perfectly. She is unaware of Kirino's hobby and generally finds anime childish and otaku disgusting, though she is on one occasion tricked into cosplaying as Kirino's favorite anime character, Meruru, for a contest and wins. Despite winning the contest, she is disgusted of what she had gone through, but likes the idea of being praised and the event even helps her career.
- Kohei Akagi (赤城 浩平Akagi Kōhei?)
- Voiced by: Junji Majima
- Kyosuke's classmate who, similar to Kyosuke, often has to support his little sister's hobby for eroge. Though unlike Kyosuke's strained relationship with Kirino, Kōhei's relationship with Sena is much better, but Kyosuke considers him somewhat of a siscon.
- Gennosuke Miura (三浦 絃之介Miura Gennosuke?)
- Voiced by: Go Inoue
- The president of the Games Research club at Kyosuke's school, which both Kyosuke and Ruri end up joining. He is also into little sister-themed eroge, as Kyosuke first meets him when trying to borrow a bike to ride home following a midnight eroge launch.
- Sena Akagi (赤城 瀬菜Akagi Sena?)
- Voiced by: Mariya Ise
- Kōhei's little sister and a member of the Games Research club, as well as Ruri's classmate. Similar to Kirino, she has an obsession with eroges, albeit she prefers the hardcore yaoi genre to an extent that she will even fantasise about her other clubmates, pairing her brother and Kyosuke as a couple and becoming visibly disappointed when Kyosuke assured her that he was straight. The relationship she has with her brother is quite strong yet it is unclear how they feel about each other. She joined the Games Research club in order to learn how to become a games designer. She is also very good at games, having the high score before Ruri beat it. This also attributes to her skill in programing, being able to debug very easily.
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