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When did Diddy and Cassie break up and how long were they together?

Sean P. Diddy Combs and Cassie Ventura at 2017 Costume Institute Gala
Diddy and Cassie were together for more than a decade. Pic credit: ©ImageCollect.com/StarMaxWorldwide

Diddy’s ex-girlfriend Cassie is pregnant with her first child with new boyfriend Alex Fine. Cassie has been dating Fine for a bit now, but not quite as long as she dated hip-hop entrepreneur Sean “Diddy” Combs.

So when did Diddy and Cassie Break up and how long were they together?

Diddy and Cassie’s relationship spanned a decade

Diddy has dated plenty of different women throughout his highly publicized career. They’ve included singer/actress Jennifer Lopez, Kimberly Porter, and singer Cassie Ventura. An Instagram photo below shows off Diddy and Cassie together for a public event. The two were seen last year at the Met Gala together.

The hip-hop pairing of Diddy and Cassie originally began their relationship way back in 2007. That was several years after Diddy’s split from J-Lo. Cassie and Combs didn’t make their relationship public knowledge for five years.

Billboard confirmed via sources that the pair stopped dating months prior to October 2018. In the video below, it’s mentioned they had a lengthy relationship together of 11 years. It was mentioned at the time of the breakup news that Diddy was “getting cozy” with a 26-year-old model named Jocelyn Chew.

So what led to the breakup? Well, there’s been a few rumors.

Back in 2015, there were reports that Diddy was dating another woman, Gina Huyn, behind Cassie’s back. Cassie is said to have found out Diddy was parading his newer girl around during the NBA All-Star weekend.

Cassie was reportedly irate about it. That is said to be what led to a break-up at the time, but it was shortlived, as Cassie went back to Diddy.

The singer attempted to call it quits again in 2016. That led to a breakup argument where Diddy lost it and Cassie’s mother ended up calling the cops on him, per TMZ.

A People report suggested that Diddy ultimately became enraged with Cassie last year when he learned of her dating Alex Fine, who was a trainer on his payroll. Cassie and Fine made their relationship public in December 2018 as a photo of them kissing at a Christmas party surfaced.

Prior to Cassie and Alex Fine going public, reports began circulating about Diddy and his alleged new girlfriend, Jocelyn Chew.

It appears both Diddy and Cassie moved on just fine. According to People, the two are now on good terms.

Cassie and Alex Fine to have their first child

After calling it quits with the nearly-50-year-old Diddy, Cassie is now with competitive bull rider Alex Fine, who is 26 years old. They’ve been dating less than a year but have shared the joyous news of expecting a child.

Cassie posted Instagram photos of her and Fine together with a caption regarding their upcoming adventure in parenthood.

“Can’t wait to meet our baby girl…Love You Always and Forever,” the singer captioned the photo series.

Cassie’s new boyfriend Alex Fine also took to Instagram to share the wonderful news. He posted a heartfelt “Letter to my daughter” along with another photo of him and Cassie together.

Fans will now await the first news and photos of Cassie’s baby bump, as well as the arrival of the baby itself in the coming months!

Matt Couden is a freelance writer for over 10 years. Matt enjoys publishing mostly about the things he loves — entertainment, sports news, and video... read more
Matt Couden

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