|Name in Japanese||櫻井秋美|
|Romaji Translation||Sakurai Akimi|
|Debut (Light Novel)||Volume 11|
|Appears in||Light Novels, Oreimo 2 Vol.8 special|
|Voice Actor (Japanese)||Ayane Sakura|
Akimi Sakurai (櫻井秋美, Sakurai Akimi) is Kyousuke's classmate during their middle school days and one of the people involved in the sudden change of Kyousuke's character from a hot-blooded student to the normal loving person he is today.
Akimi is introduced as a girl with purple colored hair styled in a bobcut. Her fashion statement is inspired by clothing an idol usually wears and includes a sleeveless blouse, a short necktie, a checkered skirt and dark-colored kneehigh socks. She also wears a small flat red ribbon on her hair. She often wears breast pads to hide her flat chest.
In Volume 12 , she wears an outfit that Kyousuke described as looking like pajamas, with the upper part looking like a bear costume hood.
At first, when Kyousuke talks about her in his flashback, she is a hikikomori who is too lazy to go to school. She was shown to be smart, getting good grades even when not attending school. She liked playing games and making fun of Kyousuke. Eventually she became more outgoing and was more open to hanging out with people and made friends. Three years later, when Kyousuke met her again, she didn't seem to change much, and was still in love with him and regretted not apologizing to him during all the years they were apart. When she found out that Kyousuke was dating his little sister, she at first got jealous and wanted to take Kyousuke for herself, though when she realized that Kyousuke chose Kirino over her, she was willing to accept it and was willing to get along with Kyousuke.
She believes that her sense of style is good and she also wears breast pads and is easily embarrassed when Kyousuke found out it was fake.
She was noted by Kyousuke and Kirino to be a strange girl, but she was popular in her class.
Originally, Kyousuke wanted to bring her back to school because she was never at class. When they met, she first found Kyousuke annoying, but he bothered her enough and completed enough of her tasks that she eventually went to school. She fell for Kyousuke and impacted him to the point that he became who he was at Volume 1. She was shocked at how different Kyousuke was when she met him again after around 3 years. In Volume 11 and 12, she was shown to still be in love with Kyousuke and was jealous of Kirino.
- It was stated By Kyousuke, that during Middle School, she was the "big sister type", but after Middle School, her appearance didn't change and she became the "Little Sister Type".
- Despite being one of the main reasons behind Kyousuke's sudden personality shift in the past, Akimi was neither shown nor mentioned in the series' anime adaptation. She only appears in the BD specials in Vol. 8.