Karei Naru Jinsei - Mina-san no Okage Desu

Karei naru Jinsei is a mixture of a board game and a dating simulation with adult content. Up to five players can compete in the board game, represented either by real players or computer AI. The board represents the life of a young male character; the different squares correspond to events that can influence his life and his relationships with the many female characters encountered on the way.

[From Mobygames]