Back to 1982: The Campus Belle Gives Me a Multiple-Choice Question

(Multiple heroines + Reborn + Period Setting + Pocket Dimension + The Richest Man) This story features multiple heroines. If that's not your thing, please move along! One day, the most beautiful girl at school asked the male lead, “If, and I mean if, both my older sister and I liked you, which one would you choose?” That's a pretty tough choice, isn't it? If you were good at reading the room, how would you answer a question like that?