Exes Cassie And Diddy Had An Uncomfortable Age Gap

Before Cassandra 'Cassie' Ventura spoke out against Sean 'Diddy' Combs, she was famously, and now infamously, one of his most high-profile ex-girlfriends. Diddy also had one of his longest relationships with Ventura, dating her on and off for approximately 11 years before the pair finally called it quits. And although many allegations have emerged about Diddy since, perhaps one of the most uncomfortable details about his life is the tremendous 17-year age gap he and Ventura shared. 

Ventura was only 19 when she first officially crossed paths with Diddy in 2005. Meanwhile, Diddy was 37 at the time. Diddy had signed "The Perfect Match" actress to his label Bad Boy Records after hearing her record "Me and You," which gained traction once Ventura promoted it on Myspace. From there, Diddy would take on a mentorship role with Ventura before their relationship quickly blossomed into something more. It seems that Ventura didn't mind how much younger she was than Diddy, given how long the two dated. However, she was reportedly hesitant to publicly confirm her relationship with the business mogul at first. 

Rumors circulated that she and Diddy were a thing in 2007. However, in 2008, Ventura allegedly attempted to dismiss the gossip as nothing but hearsay. Diddy and Ventura wouldn't confirm the rumors until 2012. As is typical of the traditionally flashy Diddy, he officially debuted his relationship with Ventura at an extravagant fashion event hosted by his supporter Kanye West.

Cassandra 'Cassie' Ventura and Sean 'Diddy' Combs would officially end their tumultuous relationship in 2018. After her split from Diddy, Ventura was quick to move on with her husband Alex Fine, who used to be her personal trainer. By all accounts, Fine and Ventura were clearly the better match. Not only was their relationship more stable, but Ventura had a much more comfortable age gap with Fine than she had with Diddy. Ventura is roughly six years older than Fine, who was reportedly born in March 1993. And although they announced their relationship a couple of months after Ventura left Diddy, they might've secretly dated a lot longer. 

In fact, Diddy reportedly discovered Ventura was having an affair with Fine. "Cassie wanted a personal trainer, so Diddy hired Alex for her. Then Cassie and Alex started hooking up before her relationship with Diddy was over," a source claimed to People. Despite the infidelity, it was alleged that Diddy and Ventura were on good terms after their breakup. Still, it seemed to take the rapper some time to get over Ventura, assuming he ever did. He once pleaded with his ex to listen to a Michael Jackson song on Instagram to remind her of their lost connection. Additionally, Diddy also put out the 2022 song "Gotta Move On," which referenced his heartbreak from losing Ventura. 

Even after Ventura and Fine had started their family, Diddy's presence still loomed over his ex-girlfriend when he congratulated the couple on having their first child. So, with everything that's come to light about Diddy after Ventura's historic lawsuit against him, it seems not being able to let her go was one of the many reasons for his downfall.