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.
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