50+ Celebrity Relationships With Age Gaps Between Them That Either Made Their Romance Work Or Led To Their Demise

Lori Harvey and P. Diddy (With a 28-year age gap)

Sean Combs, with stage names like Puff Daddy, P. Diddy, or Diddy, has been in showbiz since the early ’90s. Since then, he’s been linked to high-profile names, including pop star Jennifer Lopez. Still, among his longest relationships was with the singer Cassie.

After their romance ended, Diddy began dating socialite Lori Harvey. They had 28 years between them, which might be one of the reasons why the fling between Steve Harvey’s daughter and the rapper/record executive barely lasted three months.

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