P. Diddy

P. Diddy, whose real name is Sean Combs, once dated fellow artist Jennifer Lopez. The rapper and record producer, who made his debut album skyrocket into Billboard’s Hot 100, was in a relationship with the Dance Again hitmaker from 1999 up to 2001. Their romance started during the filming of Lopez’s debut album, making them a power couple in red-carpet events. However, things didn’t turn the way they wanted. Allegations of a third party clouded their split. Lopez once shaded their relationship, saying that she cannot attain the family life she always wanted.

As P Diddy dealt with the split, he went on to secure a more financially stable life. The rapper not only became a famous personality but was also able to make wise money management decisions. He allotted money towards expanding his wealth, from opening a clothing line, founding a television company, and starting a vodka company. The millionaire rapper is now in a relationship with model Tina Louise. The Australian runway star was reportedly building a romance with the rapper in 2020 after they were seen cozying up in Malibu.