2004 eroge from Elf.
Description from VNDB:
[i]One boy, one School year, Various girls to romance.
You play as a high school student during his last year of High school and has nine girls to pick to have a romantic relationship with.
To do so with a little luck and effort, you will have to meet with them, talk to them, get them to open up to you, date them, to capture the heart of the girl of your choice. But be careful for some girls will not be very open with dating you so easily, in those cases persistence pays off.
