Jail College

Stealing food to feed a starving family lands the hero in prison, and an experimental university program offers him a way out through his brain instead of his fists. The setup is earnest rather than ironic: he's a good man in a bad situation, trying to earn his way back to freedom.

Inside the program, he studies and answers trivia questions to progress, with correct answers opening the door to conversations, and eventually more, with the women running or attending the courses. The trivia isn't decorative background noise here, it's tied directly to how far he gets with each character, so paying attention actually matters. New women are added to the cast as the game updates, expanding who he can study his way toward without changing the basic loop of question, answer, reward.