Aitakute... Your smiles in my heart (2000)

You're in tenth grade, your parents are out of the country for a year, and your new private school has affairs of the heart as a major elective. If that isn't reason enough to get chummy with the opposite sex, you're also a teenage male, and your father has decided that he'll find you a "really nice" girlfriend if you can't do it yourself. Throw in the fact that the only person you know at this new school is a Casanova who turned down a top-ten prep school because it wasn't coed, and one has the ingredients for a good old-fashioned romance sim.