Cassie Ventura’s Ex-Boyfriend & Dating History

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Cassie Ventura has ended her relationship with rapper Sean “Diddy” Combs after 11 years. The former couple never got married — not even engaged — nor did they have any children together.

Before falling in love with Diddy, Cassie dated Ryan Leslie. The two were together from 2004 through 2007 — the same year that Cassie and Diddy were first romantically linked.

Here’s what you need to know:


She Met Diddy in 2000 & Dated Him for More Than a Decade

Cassie split

Cassie and Diddy met in the early 2000s when she inked a contract with Bad Boy Records. The two were first linked romantically in 2007, but rarely spoke about their relationship.

Back in 2013, Cassie briefly opened up about her relationship with Diddy during an interview with Madame Noire.

“Just being around him is a completely inspiring experience. Starting my own empire would be great. I’m trying to figure that out. I’m still working with Cassie Enterprises right now but I think that would be something I would love to do,” she said at the time.

Cassie and Diddy had been together for the past 11 years. The reason for their split is unknown.

“The decision was amicable and they remain friends. Cassie is going to focus on her music and acting career,” a source told People Magazine.

In recent weeks, Diddy has been romantically linked to Jocelyn Chew.


She Previously Dated Ryan Leslie

Cassie boyfriend

Before dating Diddy, Cassie was with Ryan Leslie. Leslie is a recording artist, best known for his songs, “Diamond Girl” and “How it Was Supposed to Be.” He is also the founder and CEO of SuperPhone and NextSelection Lifestyle Group.

Leslie met Cassie when she was first starting out in the business, branching from modeling into singing.

“I met Ryan [Leslie] and we recorded like 5 records and it was just for fun. Then it turned into ‘Let’s make some demos, you know put some music out’ put it on Myspace. And it went from there, it was really really organic,” Cassie told The Urban Daily in an exclusive interview.

Interestingly, it was Leslie who introduced Cassie to the “I’ll Be Missing You” singer. When TUD asked Cassie how she met Diddy, she spilled the tea.

“Through Ryan [Leslie]. He heard ‘Me and You’ in the club and he was trying to find out who the artist was. A lot of people heard the song before they saw my face,” she told the outlet.

According to popular celebrity dating database Who’s Dated Who, Ryan Leslie is currently single. His last known relationship with Kenza Fourati ended in 2011.

READ NEXT: The Funniest Memes About Diddy & Cassie’s Split


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