P Diddy’s love life explained, from JLo to Kim Porter and the scandalous drama in between

Diddy—aka Sean Combs, aka Puff Daddy, aka the mogul we can’t stop watching—has a love life that is just as dramatic as his music career. We’re talking rollercoaster highs and jaw-dropping lows, with enough twists and turns to make any reality show producer envious. From 1990s relationships with A-listers to scandals that shook the industry, here's a full rundown of Diddy's dating history that proves he’s lived life in the fast lane, leaving behind a trail of drama, accusations, and oh-so-many headlines.

Jennifer Lopez

Diddy’s relationship with Jennifer Lopez back in the late ‘90s was nothing short of iconic. They graced red carpets together and were the epitome of power couple goals—until, of course, they weren’t. J.Lo, now married to Ben Affleck (again), once told the world Diddy’s infidelity played a part in their split in 2001. But despite the breakup, Diddy, ever the gentleman (or so he wants us to think), publicly called her one of his greatest loves. Ah, the drama!

Kim Porter?

Diddy’s longest and most tragic relationship was with Kim Porter, who he started dating in the ‘90s. Together, they had four children and built a life of complicated love. Their split in 2007 was rough, but the two remained friends until her untimely death in 2018. Diddy never stopped mourning Kim, posting heartfelt tributes on what would’ve been her 50th birthday and sharing how much he valued her as the mother of his children.

Still, their relationship was far from perfect, with Diddy fathering children with other women during their on-again, off-again romance, including Sarah Chapman and Misa Hylton. A mess? Absolutely.

Cassie

After his heartbreaking split from Kim Porter, Diddy started dating singer Cassie in 2007. Their on-again, off-again relationship spanned nearly a decade, making it feel like the kind of toxic love we all secretly root for in the tabloids. But in 2023, Cassie flipped the script, dropping a bombshell lawsuit against Diddy for rape and sexual trafficking during their relationship.

The case was settled a day later—yet, we can’t help but feel like this chapter in Diddy’s love life is far from closed. Cassie, who first met Diddy when she was just 19 and he was 37, accused him of complete control over her life, even alleging he stomped on her face and forced her to hide in a hotel room to heal from bruises.

Let’s be clear: Diddy denied all allegations, claiming it was a baseless money grab, but the drama doesn’t stop there. Amidst the lawsuits, shocking footage from 2016 allegedly showed Diddy abusing Cassie. Is this really the man we’ve been listening to for decades? The plot thickens.

Yung Miami

Yung Miami, rapper and half of City Girls, and Diddy turned heads when they confirmed their romance in 2022. Their relationship was anything but conventional. “We’re dating,” Diddy declared, but later clarified there were no titles. Just vibes. That’s probably the least shocking part of their fling—if you’ve been following Diddy’s love life, you know it’s all about the vibe and not necessarily the commitment.

The two were spotted together at multiple events, including the 2023 Met Gala, looking all cozy. Yet, despite all the PDA, neither Diddy nor Yung Miami seemed too interested in the idea of putting a label on things. Single, but still dating? Gen Z relationships at their finest!

Dana Tran

In 2022, Diddy welcomed his seventh child, a baby girl named Love, with Dana Tran—a woman Diddy has not publicly confirmed he’s been romantically involved with. Dana, a cybersecurity professional and model, seems to be living life under the radar, but one thing’s for sure: Diddy’s family just keeps growing.

The final verdict?

From Jennifer Lopez to Cassie, and from Kim Porter’s tragic death to his surprise baby with Dana Tran, Diddy’s love life reads like a juicy tabloid feature. Whether he’s being accused of abuse or putting no labels on his relationships, one thing is clear: Diddy’s personal life is just as chaotic as his professional one. We’re just here for the wild ride.

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