ラブ・エスカレーター

The third high school year is about to begin, and Takashi Kurosaki decides that it should be a memorable year - at least from the point of view of romantic adventures. His best friend asks Takashi to help him win the heart of Rie, a girl whom Takashi liked in junior high school but hasn't seen much since. However, when Takashi meets Rie, he begins to realize that he may have feelings for her, and is torn between friendship and romance.

[From Moby Games]