40 Famous Men Whose Partners Keep Getting Younger and Younger
Sly Stallone and Jennifer Flavin (30 years)
While most actors go through their lives getting the occasional big role here and there, Sly Stallone has both written, and starred in some of the most iconic movies in history, including the Rocky and Rambo franchises, along with more cult-like flicks like Nighthawks, Cobra, and Demolition Man. And being a megastar the likes of Stallone, allows for the opportunities to date some very attractive young ladies, including one Jennifer Flavin, a woman 30 years his junior. The two have been married to since 1997, sharing three daughters together.
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.