People usually want a simple number when they ask how long Cassie and Diddy were a thing. But if you've followed the news over the last couple of years—especially with the explosive trial and those 2023 legal filings—you know "simple" doesn't really cover it.
Honestly, the "official" version and the reality described in court are two different beasts.
Publicly, they were the music industry’s most elusive "it" couple for about a decade. Behind the scenes, the timeline is a messy, overlapping web that started when Casandra Ventura was barely out of her teens.
The 11-Year Run (And Where It Really Started)
Most reports settle on a duration of 11 years. This usually counts the period from 2007, when things turned romantic, until their final, messy split in late 2018.
But the association actually goes back further. Cassie was 19 when she met Sean "Diddy" Combs in 2005. At the time, she was a rising model and singer with a massive club hit, "Me & U." Diddy, who was 37 and running the world at Bad Boy Records, signed her to his label.
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For the first couple of years, it was supposedly professional. Or at least, that’s what the public was told.
According to Cassie’s later testimony during Diddy’s 2025 federal trial, the shift happened around her 21st birthday in 2007. She described a confusing encounter in a Las Vegas hotel suite where the relationship turned physical. From that point on, they were tethered together in a way that would define the next decade of her life.
Why the Timeline is So Hard to Pin Down
If you try to map out their relationship on a calendar, you’re going to run into some serious overlaps. Diddy was famous for his "on-again, off-again" lifestyle.
For years, there was constant speculation about his relationship with the late Kim Porter, the mother of three of his children. Cassie testified that for a significant chunk of the early years, she was effectively being dated alongside Porter. She even mentioned a text she sent him in 2013, expressing frustration that she felt like a "side-piece" rather than the primary girlfriend.
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It wasn't just a straight line. There were breaks.
- The Kid Cudi Gap: In 2011, Cassie briefly dated rapper Scott Mescudi (Kid Cudi). This wasn't just a minor footnote; it became a major point of contention in her lawsuit, where she alleged Diddy was so enraged by the relationship that he threatened to blow up Cudi's car—an incident Cudi later corroborated.
- The 2015 Breakup: Cassie testified that she tried to leave for good in 2015 after discovering Diddy was seeing another woman. She even started a brief relationship with actor Michael B. Jordan during this window.
- The Final Straw: The end finally came in September 2018.
By the time they officially called it quits in 2018, the world saw it as a long-term celebrity partnership that had simply run its course. It wasn't until her 2023 lawsuit—and her subsequent four days of testimony in May 2025—that the public learned about the "freak-offs" and the cycle of control she claimed lasted the entire duration of those 11 years.
Key Moments in the Cassie and Diddy Timeline
To understand how long they were actually "together," you have to look at the specific milestones that defined the era.
- 2005-2006: The meeting and signing. Cassie is 19; Diddy is 37. It’s "business" only.
- 2007: The shift. Cassie testifies the romantic (and she alleges, abusive) relationship begins after a trip to Vegas.
- 2012: They finally go "Instagram official" (or the 2012 equivalent), confirming the rumors that had been swirling for five years.
- 2016: The Intercontinental Hotel incident. This is the year of the surveillance footage—leaked in 2024—showing Diddy assaulting Cassie in a hallway. Despite the violence, they stayed together for two more years.
- September 2018: The final breakup. Cassie moves out, returns the car Diddy bought her, and begins to disentangle her life.
What Really Happened at the End?
The breakup in 2018 wasn't a clean break. Cassie described a dinner at an Italian restaurant in Malibu where she tried to have a "closure conversation."
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She testified that after this dinner, Diddy forced his way into her home and raped her. This specific allegation became a focal point for defense lawyers during the trial, who tried to use text messages from the following days to suggest the encounter was consensual. Cassie’s response was simple: she was "dissociating" and trying to survive a man who had controlled her every move for over a decade.
Actionable Insights: Understanding the Context
When looking back at how long Cassie and Diddy were dating, it's easy to get lost in the gossip. But the legal proceedings of 2024 and 2025 changed the narrative forever.
- Duration isn't Depth: Just because a relationship lasts 11 years doesn't mean it was stable. The "on-and-off" nature was often a result of what Cassie described as a "cycle of abuse."
- The Power Dynamic: The age gap (18 years) and the boss-employee relationship are critical. Experts often point to this as a textbook example of grooming within the industry.
- Legal Precedent: Cassie’s decision to sue under the Adult Survivors Act in 2023 opened the floodgates for dozens of other lawsuits against Combs, eventually leading to his federal racketeering and sex trafficking charges.
If you’re researching this timeline for a project or just to satisfy curiosity, remember that the public "11-year" figure is the floor, not the ceiling. The influence began in 2005 and, in many ways, the legal battle meant the connection didn't truly "end" until the 2025 verdict.
To get a full picture of the evidence presented during the trial, you should look into the specific testimony regarding the March 2016 hotel footage and the "freak-off" logistics, which provide the most concrete documentation of what was happening during those middle years of the relationship.