Who Was Diddy Dating in 2024: What Really Happened Behind the Scenes

If you were looking at Sean "Diddy" Combs' Instagram at the start of 2024, you probably saw a man trying to project the image of a doting father and a reformed "Love" era mogul. But honestly, the reality was much messier than a curated feed. The year 2024 wasn't just another year of high-profile romances for the Bad Boy founder; it was the year his entire dating history became public evidence.

By the time the feds raided his homes in March 2024, the question of who was Diddy dating in 2024 shifted from tabloid gossip to a legal timeline. For years, Diddy’s relationships were a blur of "situationships" and "non-exclusive" pairings. But as the legal walls closed in, those close to him started speaking out—or distancing themselves as fast as humanly possible.

The Caresha Era Came to a Hard Stop

The most prominent name linked to Diddy heading into 2024 was undoubtedly Yung Miami (Caresha Brownlee).

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They were the "it" couple that wasn't quite a couple. They "went together real bad," as she famously put it. But by early 2024, the "giggles and personality" she often talked about had evaporated. Yung Miami eventually confirmed that they had officially split, though the exact timing of the breakup remained a bit blurry until she started opening up in summer interviews.

She wasn't just a girlfriend. She was a brand ambassador for his DeLeón Tequila and the face of Caresha Please on Revolt TV. When the Cassie Ventura surveillance footage from 2016 leaked in May 2024, showing Diddy assaulting Cassie in a hotel hallway, the public pressure on Miami became unbearable.

"I can’t speak on something that wasn’t my experience," she said later, basically explaining that the man she knew wasn't the man in that video. While they weren't "dating" in the traditional sense for most of 2024, her name stayed tethered to his because of the "Lil Rod" lawsuit, which alleged she was among those on a monthly stipend. She has since moved on, focusing on her solo career and her kids, but the shadow of that relationship was the biggest celebrity story of the first half of the year.

The Model Named in the Lawsuit: Jade Ramey

Then there’s Jade Ramey.

You might remember those photos of her and Diddy kissing at Nobu in Malibu back in late 2022. Fast forward to 2024, and she was forced to release a statement through her publicist. Why? Because Rodney “Lil Rod” Jones’ massive $30 million lawsuit named her specifically.

The lawsuit made some pretty heavy allegations, suggesting she was part of a group of women receiving monthly payments. Jade didn't take that sitting down. She admitted, "Yes, I dated someone," but she shot back at the idea that she was a "sex worker."

For Jade, 2024 was less about "dating" Diddy and more about defending her reputation. She expressed how "unfortunate" it was that "caring for someone or falling in love" was being scrutinized in the court of public opinion. By the time Diddy was arrested in September 2024, Jade had effectively vanished from his orbit, likely trying to put the whole "Nobu kiss" era behind her.

The "Jane" Testimony and the Private Life

While the famous names grab the headlines, the most shocking details about who Diddy was "dating" in 2024 came from courtrooms.

A woman identified only as "Jane" testified during the federal proceedings. She claimed she was in a relationship with Combs from 2021 all the way up until his arrest in 2024. This wasn't a red-carpet romance. According to her testimony, it was a relationship built on "hotel nights" and what the prosecution called "Freak Offs."

She told the jury that she stayed in the relationship because she was scared. She feared she would lose her home—where she lived with her son—if she stopped participating in the drug-fueled marathons Diddy allegedly orchestrated.

It’s a dark contrast to the "Love" persona he was trying to sell. While the public saw him with rappers and models, "Jane" described a life of coercion and control that allegedly lasted right up until the handcuffs clicked shut in Manhattan.

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Why 2024 Changed the Conversation

In previous years, Diddy’s dating life was seen as a symbol of status. If you were with Diddy, you were at the Met Gala. You were on a yacht. You were "elevated."

In 2024, that prestige turned into a liability.

• Daphne Joy, the mother of 50 Cent’s son, was also named in the Lil Rod lawsuit.
• Dana Tran, the mother of his youngest daughter, Love, mostly stayed out of the spotlight, focusing on co-parenting.
• Cassie Ventura, though not dating him in 2024, was the catalyst for everything through her 2023 lawsuit.

Basically, Diddy's "dating" life in 2024 wasn't about romance. It was about survival. Most women who had been in his circle were either testifying, filing their own suits, or staying silent to avoid being dragged into the federal racketeering case.

The Actionable Reality of the "Diddy" News Cycle

If you’ve been following this story, it’s easy to get lost in the sensationalism. But there are a few real takeaways from how the 2024 dating timeline unfolded.

1. Believe the Paper Trail, Not the IG Feed
The biggest lesson of 2024 is that social media is a mask. Diddy was posting about "Love" and "Healing" while federal investigators were building a case based on 20 years of alleged abuse. When looking at celebrity "power couples," remember you're only seeing the highlight reel.

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2. The Power of "Jane Doe"
We often focus on the famous exes like Jennifer Lopez or Cassie, but the "Jane" testimony shows that the most significant relationships in a person's life are often the ones they keep hidden. If you're following the trial updates, pay closer attention to the unnamed witnesses; they usually have the most direct information.

3. Recognize the Signs of Coercive Control
The common thread in almost every 2024 report—from Yung Miami’s "mutually beneficial" comments to Jane’s fear of losing her rent—is the use of money as a tool of control. It’s a classic red flag in any relationship, celebrity or not.

Diddy’s 2024 started with him trying to maintain his status as a legendary bachelor. It ended with his "private sex life" being the central focus of a federal criminal trial. The "Love" era is officially over.

To stay updated on the legal proceedings, you can monitor the Southern District of New York (SDNY) court filings, as more testimonies from his 2024 associates are expected to be unsealed as the trial approaches.