Evergreen Avenue (2001)

Evergreen Avenue is a Visual Novel released on PlayStation in 2001. Choosing either a male (Catan) or female (Ira) character, you must help each of the seven spirits learn the ways of human life by scheduling sessions with them each week and playing mini-games to determine your effectiveness. Events will pop up from time to time, where you have personal conversations with the various spirits or with your rival. At the end of each month, you are graded in comparison with your rival, and you must sufficiently educate the spirits by the time six months have passed.