Who: Three-time Grammy winner Sean Combs, 49 (aka P. Diddy, Puff Daddy, Diddy, Puffy, Brother Love, and briefly Swag), and Golden Globe and Grammy-nominated singer and actress Jennifer Lopez, 49 (sidebar: How has this woman not won a Grammy?!).
How They Met: Sean (Puff Daddy at the time) and Jennifer began dating around the release of Lopez’s debut album On The 6, which came out in the summer of ’99. J. Lo had recently finalized her first divorce after wedding actor Ojani Noa in 1997.
Why We Loved Them: Jen and Diddy had their own exclusive White Party on the VMA’s red carpet in 2001 and fashion has never again reached such heights.