Lori Harvey and P. Diddy (With a 28-year age gap)
Being in the entertainment business for decades, Mr. Combs has been connected to various high-profile relationships, including Jennifer Lopez. However, one of his longest relationships was with Cassie, a vocalist.
When their relationship ended, the entrepreneur began dating Lori Harvey. The two were 28 years apart, which might have explained why the romance lasted only three months.