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NEW YORK, NY – MARCH 12: Sean ‘Diddy’ Combs and Cassie Ventura attend New York Knicks Vs. Brooklyn Nets game at Barclays Center on March 12, 2017 in New York City. (Photo by James Devaney/GC Images)

Diddy And Cassie’s Road To Breakup

Diddy and Cassie have been together for years and it seemed like they’d be together forever even if they never officially tie the knot. Well, it appears like that was just a dream as it’s been confirmed that their relationship is done for. Damn, after all these years, too. That’s crazy and sad at the same damn time. So how in the hell did we get here?

Well, they started having some serious issues a few years ago and, well, just sit back, relax and let us take you on a trip through memory lane at the messy moments, rumors and break ups that led to this moment.


The First Break Up (2015) – Diddy and Cassie broke up in late 2015 amid rumors that Diddy was creeping on her at the Revolt Music Conference. It got very ugly very fast. Cassie would confirm via a meme she posted and deleted.

Back Together – After that nasty breakup, Diddy posted this IG with Cassie in the kitchen in her drawls, hinting at the notion that they were finally back together. Foreverrrrrr…nevermind

Getty Image

Cassie Living Single – In the summer of 2016, Cassie was out living her best single life because she seemed done with Diddy

We hear that the pretty brunette singer was “getting very flirty with another guy” during a party for new app MeWe at the Warwick in LA on Wednesday.

“She was looking this one guy up and down, giving him the flirty eye,” says a witness. “She was acting very much like a single woman on the prowl.”

The long-term couple had parted ways last December, but then got back together. A rep for the music mogul had no comment on his personal life.

The Cops Are Called – They tried to make things work but got into a huge argument in a car in August, 2016. The fight ended with Diddy grabbing Cassie’s phone and running off with it and the cops being called. Yikes.

Sources close to the couple tell TMZ … they got into a heated argument in a car Wednesday afternoon after Cassie told Diddy she wanted to break up.

We’re told Diddy got pissed off and suspicious enough to grab her phone and start scrolling through.

Our sources say Diddy jumped out of the car in Bev Hills — phone in hand — and she took off with the driver.

Diddy eventually came home and returned the phone, but then took 2 cars parked outside.

Cassie had told her mom about the phone incident before Diddy came home and returned it, and the mom called the cops on him.

Cops ended up at Cassie’s home and she explained she got the phone back so they left, but not before writing up a domestic incident report.

Sean Diddy Combs and Tyrese Gibson having fun at Mary J. Blige star ceremony in Los Angeles, California

Splash News

The Art Basel – Diddy was rumored to have approached a 19-year-old at Art Basel in late 2016. Here are the details:

Witnesses said Combs, a regular buyer at the art shows, approached a curvaceous 19-year-old brunette in a clingy dress — who was perusing the art with her mother — and said, “Hi, my name is Sean. You look so serene looking at art.” He then spent five minutes talking to her on Wednesday as his security guard looked on.

One witness added, “She had no idea who he was and asked where he lived, and he replied, ‘I’m between New York and LA and I have a place here.’”

Diddy wasn’t even deterred when he asked her, “Are you a collector?” and the girl, a college student, replied, “No, but my mother is.” We’re told her mother was nearby and was amused by Diddy’s approach.

The rapper then proceeded to give the girl his phone number and invited her to join him at Rockwell nightclub, where he was scheduled to appear much later that night.

The witness added that as Diddy walked away and others told the girl who he was, she added, “Isn’t he old and married?”

The Proposal? – Cassie posted a pic with a ring on her finger last September making it seem like a proposal had been made…but that does not seem to be the case.

Continue Slideshow

NEW YORK, NY – MARCH 12: Sean ‘Diddy’ Combs and Cassie Ventura attend New York Knicks Vs. Brooklyn Nets game at Barclays Center on March 12, 2017 in New York City. (Photo by James Devaney/GC Images)

January 23, 2018 – Diddy proclaims that he wants to put TWO babies in Cassie. AT LEAST. Sir.

Cassie Closely Resembles Zendaya as she Parties in NYC with Diddy after the Grammy's

247PAPS.TV / Splash News

It’s over – And now they’re broken up seemingly for good. They’ve been split for months and they seem okay with it. Damn.


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