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. The gameplay process is rather simple: each player starts a roulette, the resulting number being the number of squares the player in question moves on the linearly structured board. Beside empty squares, there are event squares with pictures, stopping on these raises the players' parameters. The squares can include money, fitness training, encounters with women, items, marriage, child birth, and even exotic choices as making a pact with the devil to raise a parameter. The player can also choose to give items to a girl of his choice. Girls will be impressed/dissatisfied with the player's actions, once a girl's parameters reach a certain level, the player is able to choose to "do the H thing" with her - in plain language, have sex.