Sean “Diddy” Combs has had a star-studded dating history throughout his years in the spotlight, and he’s been candid about finding love.
“[We learn more from] losing love. It’s the only way you kinda know how important it is,” Diddy said during a 2022 interview on Bumble’s “Luv2SeeIt” YouTube series. “All the heartache that anybody’s ever been through. That’s the thing that really makes you appreciate the times you actually felt that and actually received that love. When you lose that unconditional love is when you put some respect on love’s name.”
Diddy, who is a father of seven, was arrested two years later in September 2024 on charges of sex trafficking, racketeering, conspiracy and transportation to engage in prostitution. He denied all accusations before a judge denied multiple attempts at bail.
“We are disappointed with the decision to pursue what we believe is an unjust prosecution of Mr. Combs by the U.S. Attorney’s Office,” Diddy’s attorney Marc Agnifilo told Us Weekly in a statement at the time. “Sean ‘Diddy’ Combs is a music icon, self-made entrepreneur, loving family man and proven philanthropist who has spent the last 30 years building an empire, adoring his children and working to uplift the Black community. He is an imperfect person, but he is not a criminal.”
The statement concluded, “To his credit, Mr. Combs has been nothing but cooperative with this investigation, and he voluntarily relocated to New York last week in anticipation of these charges. Please reserve your judgment until you have all the facts. These are the acts of an innocent man with nothing to hide, and he looks forward to clearing his name in court.”
Keep scrolling to revisit Diddy’s complete dating history:
Misa Hylton
Diddy started dating fashion designer Hylton in the early 1990s.
“We were dating at the time and he had just went from intern to A&R,” Hylton recalled to BET in March 2023. “He had a new position at Uptown Records, and he was in charge of putting together the album musically, but also for their look.”
They welcomed son Justin in 1993, eventually calling it quits that same year. Hylton later said Diddy wasn’t ready to settle down so early in his career, as they continued to amicably coparent Justin.
Hylton married JoJo Brim in 1995, going on to welcome son Niko and daughter Madison. They split in 1999.
Kim Porter
After breaking up with Hylton, Diddy moved on with Porter. They were together on and off from 1994 to 2007. They welcomed son Christian in 1998 and twins D’Lila and Jessie in 2006. The music mogul also adopted Porter’s son, Quincy, from a previous relationship.
Porter died in 2018 at the age of 47 after a battle with pneumonia.
Jennifer Lopez
Diddy and Lopez were together for two years from 1999 to 2002.
“I never caught him [cheating], but I just knew. He’d say he was going to a club for a couple of hours and then never came back that night,” Lopez told Vibe in 2003, claiming that Diddy was unfaithful. “I had to think, ‘Do I want to be home with kids in 10 years, wondering where somebody is at 3 in the morning?’”
Diddy never publicly addressed Lopez’s allegations, but has frequently called the pop star one of the great loves of his life.
Lopez, who was previously married to Ojani Noa from 1997 to 1998 and Cris Judd from 2001 to 2003, later moved on with Marc Anthony. They were married from 2004 to 2014, during which they welcomed twins Max and Emme. Lopez was also engaged to Alex Rodriguez from 2019 to 2021. The next year, she reunited with ex-fiancé Ben Affleck, and they wed in 2022. Lopez and Affleck divorced two years later in 2024.
Sarah Chapman
During one of his breaks from Porter, Diddy started casually seeing Chapman. They welcomed daughter Chance in 2006.
Cassie
Diddy and Cassie (real name Casandra Ventura) were together on-and-off for a decade from 2007 to 2018. She accused him of repeated physical abuse and sexual assault in a November 2023 lawsuit, which Diddy vehemently denied. The exes settled out of court within one day.
“I have decided to resolve this matter amicably on terms that I have some level of control,” Cassie said in a statement. “I want to thank my family, fans and lawyers for their unwavering support.”
In his own statement, Diddy’s legal team stated that the settlement was “in no way an admission of wrongdoing.”
“Just so we’re clear, a decision to settle a lawsuit, especially in 2023, is in no way an admission of wrongdoing,” attorney Ben Brafman wrote in a statement shared with Us. “Mr. Combs‘ decision to settle the lawsuit does not in any way undermine his flat-out denial of the claims. He is happy they got to a mutual settlement and wishes Ms. Ventura the best.”
After Diddy and Cassie broke up, she moved on with personal trainer Alex Fine, and they got married in August 2019. Cassie and Fine share two daughters and announced in 2025 that they are expecting baby No. 3.
Yung Miami
While appearing on the City Girls rapper’s podcast in 2022, Diddy revealed that they were an item.
“We’re dating. We go on dates. We’re friends,” he said. “We go to exotic locations. We have great times.”
Yung Miami, who later stressed to XXL Mag that she and Diddy were not an exclusive couple, jointly attended the Met Gala with Diddy in May 2023. On the red carpet, Diddy also said that they “don’t put titles” on their relationship.
Dana Tran
While neither Diddy nor Tran ever publicly addressed their relationship status, news broke in September 2022 that they welcomed daughter Love Sean together.
If you or someone you know has been sexually assaulted, contact the National Sexual Assault Hotline at 1-800-656-HOPE (4673).
If you or someone you know are experiencing domestic violence, please call the National Domestic Violence Hotline at 1-800-799-7233 for confidential support.
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