1. Jennifer Lopez and Diddy

The couple broke up in 2001. Lopez later told Oprah Winfrey that she had ended the relationship because she knew she would never have the family life she wanted with the rapper.

2. Matthew Mcconoughey and Janet Jackson

The two started dating after they met at the Grammys in 1999.

3. Kim Kardishian and Nick Cannon

Kardashian West began dating Cannon following her split from Ray J, whom she dated from 2003 to 2006.

4. Madonna and Tupac Shakur

Tupac dated Madonna for a little over a year in 1993 after they were set up by pal Rosie Perez at the Soul Train Music Awards.

5. Aaliyah and Jay Z

The “Rock the Boat” artiste dated Jay Z from 2000 up until her death caused by the plane crash in 2001.

6. Tyra Banks and Seal

Banks dated Seal for a year in 1996 after her long-term relationship with the film director, John Singleton.