Monday, July 15, 2024

Visiting Sean Diddy Combs’s Relationships Over the Years


Diddy is facing allegations of sexual misconduct from four women and one man. He resolved one of these accusations, made by his former girlfriend Casandra ‘Cassie’ Ventura, outside of court. The remaining cases are still in progress.

The allegations against Diddy have sent shockwaves through the entertainment industry and have sparked a broader conversation about power dynamics and accountability. 

Each accuser (Aubrey O’Day, Azealia Banks, and Others ) have shared their personal experiences, detailing instances of unwanted advances, harassment, and other forms of misconduct allegedly perpetrated by Diddy, reports. 

And from what we have seen and heard online Diddy seems to have run away to an island after claiming that he is innocent.

Over the years, P Diddy, also known as Sean Combs, has been linked to a number of high-profile women in the entertainment industry. 

Homeland Security Investigations (HSI) raided Sean P Diddy Comb’s properties in Los Angeles and Miami today. 

As of now, there is no mention of P Diddy being named in any arrest warrant. His current location is unknown.

Sean Diddy’s relationships

From his early relationships with actresses like Jennifer Lopez and Cameron Diaz to his more recent flings with models like Naomi Campbell and Kate Upton, P Diddy’s dating history is certainly colorful. 

Despite his reputation as a ladies’ man, P Diddy has also been in long-term relationships with women like Kim Porter, with whom he shares children. Their relationship was tumultuous at times, but they remained close even after their breakup.

P Diddy’s dating life has been the subject of much speculation and gossip in the media, but he has always maintained a level of privacy when it comes to his personal relationships.

Leah Rami

Diddy is always stirring up drama, allegedly getting involved with Leah Remini after moving on from her friend Jennifer Lopez. Classic messy behavior, right?

In the past, these two were only seen together once, back in 2002. Rami was a follower of Scientology at the time and accompanied Diddy to the 59th Golden Globes. She was dressed in a style that everyone referred to as ‘Jlo style’.

Leah Rami and Sean Diddy Combs

Foxy Brown

Back in time because they worked together, Diddy and Foxy were allegedly having a romance, however nothing at that time was confirmed. 

Just recently Foxy Brown didn’t exactly defend Diddy, but she did speak positively about him. 

The Neighborhood Talk Instagram account shared her response to a comment about the situation, where she mentioned how working with Diddy gave her the “BEST OF BOTH WORLDS” with Def Jam Recordings and Bad Boy Records collaborating.

Now this could be either her speaking out because they had a good friendship or option two that they used to date. 

Sean Diddy and Foxy Brown

Misa Hylton Brim 

Misa Hylton-Brim was the first mother to his children. They crossed paths back in the 90s when Misa was only 17 years old.

Kim Porter 

Diddy had a tumultuous relationship with actress Kim Porter, who tragically passed away in 2018 at the age of 47 due to pneumonia.

They were together for 13 years before tying the knot in 1994, and they share three kids: Christian, a son, and twin daughters, Jessie and D’Lila. Their first child, 

In 2006, Porter discovered she was pregnant with their twin daughters, but learned that Diddy had fathered another child with Sarah Chapman while they were still together.

Puff Daddy has said many times that he regretted cheating and hurting Kim.

Kim Potter and Diddy

Mariah Carey 

Combs and Carey were supposedly a thing of the past, even though there was no official confirmation of them dating. 

The abundance of photos from that time on the internet, showing Sean and Mariah in close proximity, hugging each other, and being photographed together at events, says a lot. 

They could have just been friends, but how close of a friend do you have to be to let someone put their hand on your waist?

Mariah Carey and Puff Daddy in 1997

Jennifer Lopez 

Jennifer Lopez and Diddy began their relationship during one of his breaks with Porter. They were together from 1999 to 2001, but unfortunately, their relationship ended because of Diddy’s infidelity. 

During their time together, Diddy faced legal troubles. He was accused of bribery and illegal weapons.

Their love story came to an abrupt halt on Valentine’s Day, 2001, when a chaotic nightclub shootout unfolded, entangling the couple in a scandalous affair. Both of them were taken into custody, but fortunately, they were swiftly exonerated from all accusations.

Diddy and JLO

Sarah Chapman 

Diddy had a child with Chapman, his close friend, making her the third woman he welcomed a child with.

 They never had a romantic relationship, as their daughter Chance was born while Diddy was dating Porter. 

Interestingly, Diddy still leaves flirty comments on Chapman’s posts from time to time. Not much is known about their dynamic, except that they seem to co-parent well, whatever that entails.

Puff Daddy and Sarah Chapman


After ‘Puff’ and Porter ended things in 2007, he started dating Cassie, who was signed to his label Bad Boy Records. Their relationship was rocky, and they went their separate ways in 2018.

Cassie, whose real name is Cassandra Ventura, recently sued Diddy, accusing him of abusing and raping her during their complicated relationship. According to the lawsuit, Cassie and Combs met when she was 19 and he was 37, but they didn’t become romantically involved until later.

The lawsuit described Combs’ alleged violent behavior and how he reportedly assaulted his girlfriend multiple times. The case was settled the day after it was filed.

Cassie and Diddy Combs

Lori Harvey 

So…here’s the thing, before this, Lori was actually in a relationship with Christian Combs, who happens to be Diddy’s son.

Diddy and Lori Harvey had been jet-setting across the globe in 2019, from Italy to Mexico to the Big Apple. But don’t hold your breath for any official confirmation from these two – or from Steve Harvey for that matter!

Do you really think it was all innocent and friendly family ties? Take a look at the facts. I might not be a psychology expert, but seriously, HOW DO YOU DATE YOUR SON’S EX?!

Lori Harvey and Sean Diddy

Yung Miami

She and Diddy were in a situationship.

Yung Miami and Diddy caused quite a stir in 2021 with dating rumors swirling around them. However, it wasn’t until 2022 when Combs made an appearance on her podcast that they confirmed their relationship status.

But then they got the world all confused when they said that they were dating but also were single. Weird right?!!

Diddy and Yung Miami

Dana Tran

Diddy just couldn’t resist adding another baby mama to his collection, and this time it’s Dana Tran. 

The man knows how to keep things interesting, surprising the world with the arrival of his seventh child, little Miss Love, in October 2022. 

As for Diddy’s relationship with Tran, well, he’s keeping that under wraps, but they do have a joint Instagram account for their precious daughter. Talk about modern parenting, huh?

Diddy and Dana with their daughter Love

Elsa Gecaj
Elsa Gecaj
Elsa is a Gossip Columnist at TheyGossip news. She holds a Master's Degree in Journalism and Mass Communication from the University of Pristina, specializing in investigative journalism, infotainment, and fact-checking. She’s a reporter who enjoys covering about intimate relationship, celebrity news, and entertainment news. Besides her passion for journalism, she enjoys practicing yoga, singing along to her favorite songs, and painting landscapes. contact:

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