For over 10 years, music mogul Sean "Diddy" Combs and singer Cassie Ventura (best known by her first name) appeared to have one of the most promising relationships in Hollywood. But behind closed doors, this power couple’s fairytale romance eventually lost its spark. About halfway through their on-and-off relationship, the A-list pairing publicly made their relationship Instagram official in 2012, per E!. They were soon the talk of the town, between their sweet red carpet appearances and photos of their numerous luxurious vacations to Mexico, Ibiza, and France emerging, both of which showed Diddy and Cassie smiling from ear to ear (cue a chorus of "awws").
But this longtime romance hit a snag. It seemed as though "honesty and communication" — which Cassie told Vibe Vixen (via Madame Noire) were the two key components vital to "maintaining any relationship" — were what the couple lacked the most (but more on all of that below). In 2018, Diddy and Cassie called it quits for good, and heartbroken fans were left in shock.
So, what really went down between these celeb exes? They once seemed like a match made in Hollywood heaven, but let’s dive into why Diddy and Cassie split up.
Diddy and Cassie had a promising romance
Even though Diddy and Cassie were first rumored to be an item all the way back in 2007 — not long after the songstress-model was signed to the rapper’s music label, Bad Boy Records — they only confirmed their relationship five years later, per Billboard. And it wasn’t long until adoring fans and outlets were labeling "C Diddy" as #RelationshipGoals.
While the new couple continued to keep their relationship relatively private, in a rare turn, Cassie made a surprising remark about the celeb romance while speaking with Vibe Vixen (via Madame Noire) in October 2013. "Just being around him is a completely inspiring experience," she shared. Meanwhile, Diddy continued to have his new boo at the center of attention with collaborations on his various projects. In addition to producing her never-released sophomore album and having Cassie pose as a model for his Cîroc advertisements, the "Must Be Love" hitmakers made headlines when they released a super sexy (and NSFW) commercial for Diddy’s perfume, 3AM by Sean John, in 2015. "That whole interaction has nothing to do with sex as much as it has to do with love," the business mogul told Style.com (via Latina). "My concept is that love is the new sexy."
The couple also became known for jet-setting around the world in the rapper’s private plane to go on lavish beach vacations and trips to Europe throughout the mid-2010s, making pretty much everyone envious of their budding romance.
Diddy bought Cassie a ring, but it wasn’t THAT ring
Not long after Diddy and Cassie went Instagram official in 2012, whispers of an engagement began popping up in the rumor mill. E! reports that Diddy’s rep swiftly knocked down assumptions that the duo were getting hitched that April, after Cassie shared a Twitpic showing off her manicure — while also donning a "large sparkler on her ring finger." Oops.
By February 2014, however, fans once again believed things were getting pretty serious for the A-list couple, when the Bad Boy Records founder took to Instagram to share a photo of a massive diamond ring he’d bought Cassie. "Baby do you like it? I just want to get you wat you like! I just wanna Mk you smile #takeDat," he captioned the pic. Reports soon emerged surrounding the nature of the gorgeous rock, especially after the songstress shared a since-deleted Insta snap that same day of herself rocking that same piece of jewelry, according to Glamour.
Were Diddy and Cassie finally taking the next step in their relationship? Well, not exactly. Cassie reportedly "denied the engagement claims" on the social media platform, per E!. Meanwhile, Diddy’s rep told the outlet that the rumors were "not true," with E! noting that "it looks like the bling was just a (very expensive and lavish) gift and nothing else."
Cassie reportedly ‘got tired of waiting’ for Diddy to pop the question
The world was clearly anticipating Diddy to get down on one knee to pop the question to Cassie. But as years went by, did the songstress begin to question the rapper’s commitment to her? According to Hollywood Life, Cassie was reportedly ready to take their relationship to the next level, but "got tired of waiting for Diddy to put a ring on it" (for real, this time), per a source cited by the outlet. Noting "that was a big source of their issues and arguments," the insider claimed that Diddy "wasn’t ready" for such a huge commitment, but added, "He did leave room for her to believe that eventually the ring would come. But it never did."
Was a pattern beginning to form with Diddy? Before he was with Cassie, the rapper shared an on-and-off-again relationship with late model Kim Porter from 1994 until 2007. However, he never seemed to want to take it to the next level. After Porter’s tragic death in November 2018, Diddy shared an affectionate post on Instagram, professing his love to Porter, who’s also the mother of three of his children. When questioned in the comments about never marrying, Diddy replied, "Just didn’t happen. That had nothing to do with the love," adding, "I wasn’t ready and that’s it. I’m ready now but it’s [too] late. Don’t be like me."
Perhaps the same situation was playing out between Diddy and Cassie.
Here’s why Diddy wasn’t ‘ready’ to settle down with Cassie
As the years went by in this on-and-off couple’s relationship, fans grew more confused as to why Diddy didn’t appear to want to commit to Cassie and propose already. Was the rapper doubting the seriousness of their relationship? Or, was Diddy just a guy who simply didn’t believe in marriage?
While appearing on The View in 2013, Diddy opened up about the matter and shared his thoughts on marriage. "It definitely would be a dream come true for me to just one day be ready for that," Diddy began (via E!). "I’m not really looking because I know the responsibility that comes with that and I think that a lot of people, they jump into that and they’re not honest with themselves. I’m brutally honest with myself. I don’t want to get married and not make that woman be the best."
But was there something else brewing beneath the surface of this celebrity relationship that made the rapper hesitant to get down on one knee?
A serious fight between Diddy and Cassie led to police intervention
Diddy and Cassie broke up on a number of occasions throughout their decade-plus relationship, but things reportedly escalated between the two when police were called to the model-singer’s home in Los Angeles over a domestic dispute in August 2016. TMZ reports that, after Cassie told the rapper their relationship was over while in a car, the two "got into a heated argument." Diddy allegedly "got pissed off and suspicious enough to grab her phone and start scrolling through," before "jump[ing] out of the car" with her "phone in hand."
Later that day, Diddy returned the phone to Cassie, but her mother had already called the police to intervene. They cited the domestic incident, but that seemed to be the end of the story. The dispute resulted in the two breaking up, before forgiving one another shortly after, per E!. Unfortunately, this incident came at a time when Diddy and Cassie were already better known for their "roller-coaster relationship" than for being #RelationshipGoals. According to Page Six, the couple had previously temporarily split in December 2015.
However, as E! noted, whenever the two did go on a "break," it was never thought to be permanent. "He loves her so much so likely it won’t be a long break," an insider shared with the outlet. "He always finds a way of coming back to her."
Was Diddy and Cassie’s romance plagued by infidelity?
Not unlike his relationship with Jennifer Lopez, Cassie and Diddy were plagued by infidelity rumors toward the end of their on-and-off romance. In the summer of 2016, Page Six reported that the "Me & U" singer was allegedly caught "flirting" with other men while things were back on with Diddy. A source cited by the outlet claimed that Cassie "was acting very much like a single woman on the prowl" when she attended a party in Los Angeles.
However, Cassie wasn’t the only one accused of cheating. Two years later, serious allegations were made against Diddy by a woman who went by T. George. She not only claimed that she had a secret affair with rapper for about a year and a half while he was dating Cassie, but even went so far as to allege that he was her child’s father, according to Dallas Black. Citing the Instagram blog Fameolous, the outlet revealed that the rapper reportedly took a DNA test to prove he was not the father — and, it turns out, he wasn’t.
Unfortunately, it seemed as though Diddy and Cassie could not overcome the ongoing cheating rumors.
Diddy and Cassie call it quits for good this time
Sadly, after over a decade of dating, Diddy and Cassie called it quits once and for all by October 2018. According to a LoveBScott exclusive, Cassie’s rep stated, "They are indeed no longer together and haven’t been for months." Newsweek reports that Cassie, who hadn’t shared an Instagram pic with Diddy since that May (which was later deleted), had unfollowed most accounts on the social media platform — notably including Diddy’s — while seemingly wanting to start fresh after the breakup. She also shared what appeared to be a cryptic message to her famous ex-boyfriend on her Instagram Stories, writing, "F**k these hoes." Yikes.
While the stars didn’t publicly addressed their split at the time, The Sun claimed that Cassie had "grown tired" of dealing with the damaging cheating rumors, which reportedly "eventually sent her over the edge." According to the Daily Mail, Diddy (then 49) was supposedly already seeing 26-year-old Canadian model Jocelyn Chew when his breakup with Cassie made headlines. But he wasn’t the only one moving on: at the time, Cassie was also rumored to be with a new man, who Diddy knew all too well.
Did Diddy feel ‘betrayed’ by Cassie after their split?
Not long after Diddy and Cassie had broken up for good, some seemingly shady reports emerged surrounding the singer’s new relationship with personal trainer Alex Fine. According to a source cited by People in January 2019, Diddy had hired Fine, and the timing of Cassie’s blossoming romance reportedly led the Bad Boy Records founder to think that "there was absolutely overlap." The insider added, "Cassie and Alex started hooking up before her relationship with Diddy was over." Additional sources from Diddy’s camp told TMZ that the rapper felt "betrayed" by his ex.
For her part, Cassie, who went Instagram official with Fine in December 2018, denied the cheating allegations, with sources telling TMZ that she felt Diddy’s "timeline is wrong," while "insist[ing]" that she and Fine "did NOT start dating until after she broke up with Diddy."
Despite the ongoing infidelity claims, another source told People that Diddy and Cassie’s breakup wasn’t all that dramatic, alleging that the "decision was amicable and they remain friends." We’re hoping the latter claims are true.
Cassie quickly moved on after calling it quits with Diddy
It seems as though Cassie’s relationship with Alex Fine couldn’t be more different from her previous private romance with Diddy. After filling her Instagram feed with more photos of herself with Fine, the singer dropped a bombshell on her followers in June 2019, when she announced that she was already pregnant with her first child with the personal trainer. For his part, Fine shared the baby news with a note to his future daughter, writing in part, "I promise to be a man that you and your mother look up to and love. I will always listen and put the both of you first."
The couple also wasted no time getting hitched. Fine proposed to the songstress on Aug. 24, 2019, and just a few weeks after, the happy pairing tied the knot in an intimate ceremony in Malibu, Calif. To recap: in the first 12 months since her split from Diddy, Cassie got engaged, married, and later welcomed her daughter, named Frankie Fine, in December 2019 (via TMZ).
Thankfully, there seemed to be no bad blood between Cassie and her music mogul ex, who even congratulated the new parents back when they announced they were expecting. Alongside a photo of Cassie and her new man, Diddy (who was linked with Lori Harvey at the time) wrote alongside three heart emojis on Instagram, "Congratulations, @Cassie and Alex. I wish you nothing but love and happiness. God bless." (Though he notably didn’t tag Fine.)
Cassie opened up about her post-breakup ‘journey’
As of this writing, Cassie has never publicly explained the true reasonings behind her split from Diddy. But she did open up about a "journey" she’d gone through since she was with the rapper. In October 2019, the singer took to Instagram to share a snapshot of herself looking out a window from May 2017, and included a lengthy caption.
"Do you ever come across old pictures of yourself and get blown away by how much you’ve evolved?" Cassie asked her followers, before reflecting, "I feel sad for the girl in the picture because I know the personal demons she was battling, but I’m so excited for her growth to come." She continued, "It’s bittersweet looking at this photo. This is a shout out to everyone on their journey! I’m still on mine and I hope that me sharing can help others know that there is so much joy in recognizing your growth every step of the way."
This marked the first time Cassie even publicly hinted at her previous relationship with Diddy, so it was a surprising yet comforting look at the singer’s ability to move on and share her headspace with fans.
How does Diddy and Cassie’s relationship look today?
As of this writing in 2021, both Diddy and Cassie have remained decidedly mum on their actual breakup — but there thankfully doesn’t seem to be any love lost between the former couple.
E! reports that the last time the exes were seen in public together was shortly after the mother of three of Diddy’s six children, model Kim Porter, suddenly passed away in November 2018. Prior to getting together in Los Angeles, Cassie reportedly "reached out" to her former flame via text, "checking up on him and expressing her condolences," a source told the outlet. Diddy, for his part, was reportedly "pleasantly surprised" and "very touched."
Despite remaining on good terms, it doesn’t seem like the two have had much contact with one another since. In fact, according to CheatSheet, Diddy and Cassie supposedly share a "non-existent" relationship — which, by Hollywood standards, is actually pretty darn healthy. Looking at both of their Instagram accounts these days, Cassie is busy focusing on her growing family with husband Alex Fine, while Diddy has similarly shared numerous photos of his own children.