To Heart (1999)

Adapted from a dating sim game of the same name. Fujita Hiroyuki is an always sleepy and difficult to motivate high school boy, but he has a kind heart, and the gift to make friends with girls easily, like his good childhood friend Kamigishi Akari who has always looked out for him. They hang out with the calm Satou Masashi and the hyperactive Nagaoka Shiho from the parallel class, navigating the challenges of school and daily life - such as seating placement in class, clean-up duty, or going for karaoke. With both of them are in the same class in high school, their love towards each other begin to accumulate, slowly but day by day. However there are many cute girls around.