The timeline of Sean "Diddy" Combs and Casandra "Cassie" Ventura is, frankly, a lot to untangle. It’s not just about when they first appeared on a red carpet together. To understand when did cassie start dating diddy, you have to look past the glitzy Instagram posts from the 2010s and go back to a much darker, more complicated beginning.
Honestly, the "official" dates and the actual reality of their start have shifted depending on who was telling the story—until the 2023 lawsuit and the 2025 trial brought everything into the light.
The Professional Start: 2005 to 2006
It all kicked off in 2005. Cassie was just 19 years old. She was a rising star, a model, and a singer with a massive hit "Me & U" that was bubbling up in the clubs. Diddy was 37. He was the mogul, the gatekeeper of Bad Boy Records.
He didn't just find her; he pursued her professional talent. He signed her to a joint venture with Bad Boy. At the time, Diddy was still very much "on" with the late Kim Porter, the mother of his children. For a while, Cassie was just the new face of the label. She was the spokesmodel for Sean John. But the power dynamic was already skewed.
When Did Cassie Start Dating Diddy? The 2007 Shift
While they met in 2005, the romantic—and allegedly abusive—relationship really took root in 2007.
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According to Cassie’s own testimony during the federal trial in 2025, things took a definitive turn around her 21st birthday. She testified that Combs first kissed her then, marking the transition from a boss-employee relationship to something far more intimate and, as she described it, "viciously" controlling.
"He lured her into an ostentatious, fast-paced, and drug-fueled lifestyle... her boss, nearly two decades her senior."
— Excerpt from the 2023 Lawsuit
By late 2007, the rumors were everywhere. They were "linked," but they weren't "public." Diddy was notorious for keeping his private life in a state of flux, often overlapping relationships or refusing to put a label on things while he was still connected to Kim Porter.
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The Public Reveal (2012)
It took five years of being "linked" before they actually went public. Five years.
In 2012, they finally stopped playing the "just friends" game. They started showing up at Paris Fashion Week and movie premieres as a couple. By then, the public saw them as this high-fashion, ultra-rich power duo. But behind the scenes, the timeline was already fractured by what Cassie later described as a "cycle of abuse."
A Quick Breakdown of the Key Years:
- 2005: They meet (Cassie is 19).
- 2007: The romantic relationship officially begins (per legal documents).
- 2012: They finally go public.
- 2015: A temporary split (Cassie posts "I'm single" on IG).
- 2016: The infamous hotel hallway incident (captured on CCTV).
- 2018: The final, permanent breakup.
Why the Start Date Matters
The reason people keep asking "when did cassie start dating diddy" isn't just for celebrity gossip. It’s because the date matters for the legal cases that followed.
If the relationship started in 2007, it means she was under his influence for over a decade. The 2025 trial, where Cassie was the star witness, hinged on this timeline. The defense tried to paint their early years as a "consensual, loving romance," but Cassie's testimony painted a picture of a 19-year-old being groomed by a man with unlimited resources.
She described a world of "Freak Offs" and "hotel nights" that started much earlier than anyone realized. It wasn't a sudden shift; it was a slow, creeping control that began almost as soon as she signed that record deal.
The End and the Aftermath
The relationship finally sputtered out for good in 2018. Diddy was seen with other women, and Cassie's team released a statement saying they hadn't been together for months.
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What's crazy is how fast she moved on once she was truly free. By 2019, she was married to Alex Fine. They have three kids now. It felt like she was making up for lost time—literally.
The 2023 lawsuit, which settled for a rumored $20 million in just 24 hours, was the first time the world really saw the 2007–2018 timeline for what it allegedly was: a decade of "violence and sex trafficking" rather than a glamorous Hollywood romance.
Actionable Insights: Understanding the Dynamics
When looking at high-profile timelines like this, it's easy to get lost in the dates. But there are a few real-world takeaways from how this unfolded:
- Power Imbalances: A 20-year age gap combined with a boss/employee relationship is a massive red flag in any industry.
- The "Slow Burn" of Control: Abuse doesn't always start on day one. It often starts after a period of "love bombing" or professional mentorship.
- Documentation: The reason Cassie’s case was so strong was because of the trail left behind—emails, texts, and eventually, that 2016 video.
If you’re following the legal fallout of the Sean Combs trial, remember that the "dating" part of the story is only the surface. The real story is the eleven years that happened between that first kiss in 2007 and the final break in 2018.
Verify your sources when reading about these timelines, as many early reports from 2007–2012 were heavily curated by PR teams to hide the reality of the situation. The court documents from 2023 and the 2025 trial testimony are currently the most accurate records of what actually happened.