Sean ‘Diddy’ Combs’ is currently on trial facing charges of sex trafficking, racketeering and transportation to engage in prostitution. He also faces a slate of sexual assault and abuse charges dating from 1991 to last year. Combs denies all allegations and has pleaded not guilty in court.
Given his status as a music mogul, there are few names in Hollywood that Combs hasn’t worked with, been friends with or hosted at one of his parties over the years. Unfortunately, that means his close relationships are being revisited in a new light.
When did Jennifer Lopez date P Diddy?
That includes Jennifer Lopez who, while not at all implicated in Combs’ active legal proceedings, dated the rapper between 1999 and 2001. Let’s be honest, it’s not a great time to have any association with Combs at all, never mind a romantic history.
How did Jennifer Lopez and Diddy meet?
They met on the set of Lopez’s music video for ‘If You Had My Love’ and made their red carpet debut at the MTV Video Music Awards in September 1999. She described him as a mentor in the early stages of her career, but has since admitted it was a ‘crazy, heightened time’ and that the relationship caused her emotional distress.
One of the most famous couples in Hollywood at the time, their relationship was marked by glamorous events, cheating scandals and turbulence.
Why was Jennifer Lopez arrested with Diddy? The 1999 shooting explained
In 1999, for example, the couple was arrested after a night out in New York turned violent. They were pulled over by the police after fleeing the scene of a gunfire incident where three people were injured and a firearm was discovered in their car. They were arrested alongside Combs' bodyguard Anthony 'Wolf' Jones and rapper Jamal 'Shyne' Barrow and it became a media frenzy for all involved. Lopez was released without charges after 14 hours in custody, but Combs faced weapons and bribery charges. He was later acquitted. Barrow, then 21, was convicted of assault and gun possession and sentenced to 10 years in prison.
However, one of the victims of the shooting, Natania Reuben, claims Combs shot her in the face. She survived the shooting, but the bullet scarred her brain. When her daughter told her that Combs had been arrested last September, she told The Daily Beast: 'I said, "Are you kidding me, really?" She said, "Yes!" I just screamed out to God, "Thank you, merciful father!" One of the best days ever.' Combs has not publicly responded to this specific allegation.
Reuben said she has lived with the consequences of the shooting ever since. 'I’ve had a host of problems, not the least of which is a traumatic brain injury, because the bullet scarred my brain.'
In 2011, Combs settled a multimillion dollar lawsuit with the three people involved in the 1999 shooting, the details of which were never published due to a confidentiality agreement.
Why did Diddy and J.Lo break up?
Brushes with jail time aside, Lopez and Combs’ relationship was reportedly toxic in other ways too. Combs allegedly got caught up in ‘the hype’ of Lopez’ shared fame and used their high-profile relationship to irk his former partner and ‘love of his life’, Kim Porter, who he went on to have three children with.
Porter herself said the relationship was ‘not real’ and that she knew that Combs was still in love with her. In a 2007 interview with Essence, the rapper admitted that he had hoped dating Lopez would make Porter ‘come running after me’.
They announced their split on Valentine’s Day in 2001 with Lopez offering her reasons in an interview with Vibe magazine in 2003. ‘I never caught him, but I just knew,’ she said. ‘He’d say he was going to a club for a couple of hours and then never come back that night. It was the first time I was with someone who wasn’t faithful. I was in this relationship with Puff where I was totally crying, crazy and going nuts, it really took my life in a tailspin.’
Both Lopez and Combs were in their early 30s at the time and Combs went on to briefly date Naomi Campbell before rekindling with Porter in 2003. Lopez famously went on to date Ben Affleck after meeting him on the set of Gigli in 2001, they got engaged the following year but called off the wedding and broke up in 2004.
Will Jennifer Lopez testify against Diddy?
Of course, the lore surrounding Lopez and Combs’ two-year relationship has taken a dark turn in recent months, especially since several of the allegations leveraged at Combs took place during the period of their relationship. One lawsuit filed by Thalia Graves, for example, alleges that Combs and his security drugged and raped her in 2001 when she was 25 years old, and that they recorded the incident.
This is one of many serious allegations facing Combs. In October, lawyer Tony Buzbee filed as many as 120 new lawsuits covering alleged assaults that took place between the 2000s and the 2010s, 25 of whom were minors at the time. Combs vehemently denies all allegations.
These are allegations Combs' defence team will be forced to contend with in court. One week in and Combs' trial is already dominating the headlines. Not only has the court heard from Daniel Phillip, a former escort allegedly hired by Combs to have sex with his then-girlfriend Cassie Ventura on multiple occasions, but it has heard from Ventura herself.
In 2023, Ventura filed a lawsuit against Combs alleging that he subjected her to a pattern of control and abuse over a decade. At the time, he denied the allegations, but in May last year CCTV footage from 2016 showed him violently kicking and beating her outside their hotel room. The following day he issued an apology on social media and the lawsuit was settled out of court for $20 million (£15m). This week, however, Ventura has testified before the jury and described the abusive nature of their relationship. 'I can't carry this anymore,' she told the court. 'I can't carry the shame, the guilt, the way he treated people like they were disposable. What's right is right, what's wrong is wrong. I came here to do the right thing.'
There is also increasing anticipation of the ‘Diddy List’, a compilation of the celebrities linked with Combs who may have been aware of or complicit in his alleged crimes. Ahead of the trial, the judge Arun Subramanian joked, 'I read through the people and places list, which is several pages long. I felt I was reading an appendix from, like, The Lord of the Rings.'
While she does not face any allegations herself, Lopez is one such name. Since Combs’ arrest last September, she has been asked about his case several times during press junkets and red carpet appearances and has repeatedly remained quiet.
In late October, a fan asked ‘JLo, do you have any comments about Diddy and the allegations?’ during an autograph signing. She immediately stopped signing autographs and left the event. She once described their relationship as ‘emotionally exhausting’ and it seems more than 20 years later it is coming back to haunt her again.
Nikki Peach is a writer at Grazia UK, working across pop culture, TV and news. She has also written for the i, i-D and the New Statesman Media Group and covers all things TV for Grazia (treating high and lowbrow shows with equal respect).