Sean 'Diddy' Combs' Relationship Timeline: From Jennifer Lopez to Cassie Ventura

8 High-Profile Relationships of Sean Diddy Combs 

Sean Combs, popularly known as 'Diddy', has had a storied career and an equally eventful love life. Rising to fame in the 1990s, the rapper has been linked to various high-profile celebrities over the years, often followed by controversies, serious allegations, and legal battles. From his early days with Misa Hylton to his rollercoaster relationship with Cassie, Diddy’s love life continues to make headlines. Here's a comprehensive look at Diddy's past girlfriends and the significant chapters they represent in his life.

1. Misa Hylton

Diddy’s first prominent public relationship was with fashion designer, Hylton, in the early 1990s. Their relationship coincided with Diddy’s burgeoning career in the music industry. Hylton credits Diddy with helping her get her big break, hiring her to style the music group, Jodeci. They welcomed their son Justin on December 30, 1993. However, their romantic relationship ended soon after Justin’s birth. In an interview, she shared, “We were dating at the time and he had just gone from intern to A&R. He had a new position at Uptown Records and he was in charge of putting together the album musically but also for their look.” Hylton shared cryptic comments in 2023 regarding Diddy’s lawsuit. She wrote, "This [is] where the buck stops…Everyone has to sit around for years and act like there isn’t anything wrong with you."

2. Kim Porter

Diddy’s longest relationship was with Kim Porter, whom he also dated in the 1990s. They shared a deep bond and had three children together. Their relationship was a rollercoaster ride, including a breakup in 2006 when Diddy was expecting a child with Sarah Chapman while Porter was pregnant with twins. Back then she said, “I would have preferred to find out from him because that’s a man. 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. 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.” She further added, “...I was like, ‘Dude, this is so wack I can’t even respect you right now.’ And for me, once the respect is gone, I’m not even listening to you.” Despite the heartbreak, Porter and Diddy remained close friends until her untimely death in 2018 from lobar pneumonia.

3. Jennifer Lopez

Diddy and Jennifer Lopez’s relationship in the late 1990s and early 2000s was the talk of Tinseltown. They were a power couple, attending high-profile events together, including the 2000 Grammy Awards when Lopez famously wore her green Versace dress. He said, "I thought it was gonna change the game as far as for her and fashion. I didn't know how big it was gonna be, but it was a great moment for her. She deserved it. She is one of the fliest out there." Their romance, however, ended in 2001, with Lopez later citing Diddy’s infidelity as the cause, as reported by Page Six.

4. Sarah Chapman

As per People magazine, Sarah Chapman and Diddy never officially dated, but their friendship resulted in the birth of their daughter, Chance, in 2006. This period was marked by controversy as it coincided with Diddy’s relationship with Porter. Despite the scandal, Diddy and Chapman have maintained a positive bond, co-parenting harmoniously. Diddy frequently expresses his gratitude for Chapman on social media, celebrating her role in their daughter's life. In 2023, Diddy wrote, “Thank God for you every day! We are so grateful to have you in our lives! Love you.”

5. Cassie Ventura

Following his final split with Porter, Diddy dated singer, Cassie Ventura, in 2007. Their on-again, off-again romance lasted over a decade until 2018. Subsequently, in 2023, Cassie filed a lawsuit against Diddy, accusing him of rape and sexual trafficking. In a statement she said, “After years in silence and darkness, I am finally ready to tell my story, and to speak up on behalf of myself and for the benefit of other women who face violence and abuse in their relationships. With the expiration of New York’s Adult Survivors Act fast approaching, it became clear that this was an opportunity to speak up about the trauma I have experienced and that I will be recovering from for the rest of my life.” The complaint read, “She found herself becoming numb to the abuse she was experiencing, and became entirely beholden to Mr. Combs’s demands...She began to blindly follow his instructions out of fear of again being on the receiving end of a vicious beating.” However, Diddy’s lawyer denied the allegations. The lawsuit was settled the following day as she released a statement, “I have decided to resolve this matter amicably on terms that I have some level of control over. I want to thank my family, fans, and lawyers for their unwavering support.”

6. Lori Harvey

In 2019, Diddy was rumored to be dating Lori Harvey, daughter of comedian, Steve Harvey. Their relationship was short-lived but highly publicized, marked by a vacation with Lori’s family in Italy and their appearances together in New York City. However, later that year, the pair parted ways, with Lori unfollowing Diddy on social media. She later added, "It's so funny because I'm so quiet...there's been so many stories that have been made up about me. I've seen stories about me being fully in love with somebody, and we have this whole relationship, and I'll see the guy, and I'm like, 'I've never even met him before.'"

7. Yung Miami

Diddy and City Girls rapper, Caresha Brownlee a.k.a Yung Miami, began dating in 2021. Their relationship, characterized by its casual and non-exclusive nature, was confirmed in June 2022. Diddy stated, "We're dating. We do have dates. We're friends. We go to exotic locations. We have great times." Later on, Miami remarked, "We are dating. We are single, but we're dating. People don't know what dating means. He's single, I'm single, but we're dating." Their dynamic reflects a modern approach to relationships.

8. Dana Tran

Although Diddy has not publicly confirmed a romantic relationship with Dana Tran, she is the mother of his seventh child, Love Sean Combs, born in October 2022. Tran, a cybersecurity professional, has maintained a low profile, and their relationship details remain private. Diddy announced the birth of Love on social media, expressing his gratitude for Tran and his excitement about his growing family. He wrote, "I'm so blessed to welcome my baby girl Love Sean Combs to the world. Mama Combs, Quincy, Justin, Christian, Chance, D'Lila, Jessie, and I, all love you so much! God is the Greatest!"