Kakyuusei

In Kakyuusei, the player takes the role of a young Japanese high-school student named Kentarou. During the spring break, Kentarou has been working in a restaurant, run by a relative of his family. Now, as the final school year has come, with some money in his pocket and plenty of interest towards representatives of the fairer sex, Kentarou is determined to make this school year memorable...

[Edited from MobyGames]