Jailed Diddy's Rollercoaster Love Life Laid Bare: From Tragic Death of Ex to Cameron Diaz Romance Rumor — and 2-Year J Lo Relationship

Sean "Diddy" Combs started dating fashion designer Misa Hylton in the early 1990s. They welcomed their son, Justin Combs, though they called it quits shortly after they found out about Misa's pregnancy.

While they remained friends after their breakup, Misa called out the music mogul following Justin's arrest in 2023 as she believed he became a bad example to their son.

"I'm not protecting no one anymore, just my son," she wrote online. "The statement 'a fish rots from the head down' means that, in addition to being a major contributing factor in a family or organization's success, leadership is also the root cause of its failure and demise."

Soon after his split from Misa, Diddy moved on with Kim Porter and welcomed their child, Christian, on April 1, 1998. However, things fell apart when she found out Diddy fathered a child with his friend Sarah Chapman.

"I would have preferred to find out from him because that's a man," she told Essence. "I know it's hard for anyone to say to their significant other, 'I've gotten into some s--- and I got a baby on the way.' But men do get caught up in things; I'm not naive to that."

Kim, who died in 2018, added, "Still, there's a right and a wrong way to handle it. Because, most of all, we were friends. Even if I couldn't have understood it as a woman, I would have understood it as a friend."

In 1999, the record executive and Jennifer Lopez became an item and dated each other for two years before ultimately calling it quits due to his alleged infidelity.

"I never caught him but I just knew. He'd say he was going to a club for a couple of hours and then never come back that night," Jennifer said in 2003.

Despite ending their romance, Diddy admitted she was one of his greatest lovers.

Diddy's third baby mama gave birth to their child, Chance, months before Kim delivered their twins. They never formally dated but grew close to each other as they raised their daughter together.

While Diddy and Cameron Diaz never confirmed their rumored romantic relationship, several sources said they hooked up from 2008 to 2012.

Diddy and Casandra "Cassie" Ventura struck up a romance in 2007 but only confirmed their relationship in 2012. Two years later, they sparked wedding rumors but reportedly split in 2015.

They went on to date on and off from 2015 to 2018 until they broke up for good.

In November, Cassie dropped a bombshell lawsuit accusing the record producer of abusing her for years after they met when she was 19.

"She found herself becoming numb to the abuse she was experiencing, and became entirely beholden to Mr. Combs's demands," the complaint disclosed. "She began to blindly follow his instructions out of fear of again being on the receiving end of a vicious beating."

On the other hand, Diddy dismissed the claims in a statement through his lawyer, who called the allegations "offensive and outrageous." Only a day after the filing, he confirmed they decided to settle the issues privately.

In May, a 2016 surveillance video made rounds online, showing Diddy physically assaulting Cassie during an altercation in a California hotel.

In July 2019, Diddy ignited dating rumors with Lori Harvey after they were seen spending time together in different outings. However, the buzz died down when she unfollowed him on social media after the news about him having dinner with a mystery woman surfaced.

Lori formally denied the romance rumors in January 2023 while refuting the claims she also dated his son Justin.

Diddy was linked to City Girls rapper Yung Miami in 2021 but only confirmed their romance in June 2022.

During his appearance on her podcast, Diddy said they dated after the female artist asked him, "What we is? [sic]"

"We're dating. We go have dates. We're friends. We go to exotic locations. We have great times," said Diddy.

However, Yung Miami clarified the comments in her interview with XXL Mag, explaining, "We single, but we're dating."

Diddy welcomed his child, Love, with Dana Tran in October 2022. Though they never confirmed their relationship, he openly spoke about the baby mama.

"I'm so blessed to welcome my baby girl Love Sean Combs to the world," he wrote. "Mama Combs, Quincy, Justin, Christian, Chance, D'Lila, Jessie and myself all love you so much! God is the Greatest!"