Diddy and Lori Harvey (28 years)
Affectionately known as P. Diddy, or Puff Daddy, or just Diddy, Sean Combs is one of the most successful and talented entrepreneurs to come out of the mean streets of New York City. Getting his start as a rapper in the early 90’s. P. Diddy was able to parlay his early popularity into a career as one of the most successful record producers of his generation, making him both famous and incredibly wealthy, and with fame and wealth come the ladies, and Diddy has had his fair share, including the much younger Lori Harvey.