2. Holly Madison and Hugh Hefner
Is anybody really shocked that these two regret dating one another? Holly Madison has promoted her latest memoir all summer long, where she reveals how much she hated being in a relationship withHugh Hefner, the man who would go on to change the model’s life forever. While many perks came with living at the mansion, Holly says that Hugh definitely had her in control — as a grown adult, she was still given allowances and curfews which she had to follow. Oh, and there was sex involved whenever Hugh wanted it. Yikes!
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