When Were Diddy & Cassie In A Relationship?

With the news breaking that Diddy is being sued for $30 million by his former flame Cassie, some fans might be wondering about the two stars’ relationship. After all, most of the headlines about the music mogul’s love life lately have revolved around his links to City Girls rapper Yung Miami. But before their connection, Casandra Ventura was Sean Combs’ original age-inappropriate paramour.

The two became connected after the release of Cassie’s hit single “Me & U” in 2006. Diddy heard “Me & U” in a club, and the song’s producer, Ryan Leslie, convinced him to support her debut album under both their imprints, Bad Boy Records and NextSelection, respectively. They went public with their relationship in 2012, appearing at events such as Kanye West’s fashion show in Paris that year.

However, by 2015, the couple appeared to have hit the rocks, with reports that they split up in December making the gossip blog rounds. They briefly reunited, until police were reportedly called to Cassie’s home when she tried to break up with him again in 2016. They were seen together again at the 2017 Met Gala, but by 2018, had apparently broken up again for the final time.

Cassie was eventually linked with fitness trainer Alex Fine that year; they married in 2019 and had two children together. In her lawsuit, she alleges that Diddy was abusive throughout their relationship, raped her in 2018 after forcing his way into her home, and that he even blew up Kid Cudi’s car in a fit of jealousy after their last breakup.