Lori Harvey and P. Diddy (With a 28-year age gap)
Sean Combs has been in show business for decades, and as a result, he has been linked to a number of high-profile partnerships, including Jennifer Lopez. However, one of the longest was with Cassie, a singer.
When their relationship ended, the entrepreneur started dating Lori Harvey. The two were 28 years apart in age, which could explain why the romance barely lasted three months.