Sean ‘Diddy’ Combs’ trial is set to take place in May next year – now that he has been denied bail for a third time, it’s on track to become one of the most high-profile court cases of the past decade.

He is currently being held in the Metropolitan Detention Centre in New York on charges of sex trafficking, racketeering and transportation to engage in prostitution, and faces a slate of sexual assault and abuse charges dating from 1991 to earlier this year.

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.

That includes Jennifer Lopez who, while not at all implicated in Combs’ active legal proceedings, dated the rapper from 1999 to 2001. Let’s be honest, it’s not a great time to have any association with Combs at all, never mind a romantic history.

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.

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 and a firearm was discovered in their car. The arrest 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.

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 years later 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 of their relationship 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. The pair later reunited in 2021, got married in 2022 and announced that they were getting divorced in August.

In fact, music executive Suge Knight alleges that the reason they got divorced was because Affleck knew details about Lopez’s relationship with Combs, including what really happened on the night of the aforementioned shooting. On his podcast, Collect Call with Suge Knight, the executive suggested that the FBI had shown Affleck tapes of his wife admitting to knowing more about the case. ‘I’m quite sure they said, “We want to show you some things about your wife”,’ he added. Knight’s claims, which he made from prison where he is serving a 28-year sentence for manslaughter, remain unproven and unsubstantiated. 

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.

With such a voluminous amount of material to get through ahead of his trial in May, Combs’ legal team are doing all that they can to get him out on bail – as is Combs himself. Last week, the prosecution alleged that Combs had been using the phone accounts of at least eight other inmates to contact potential witnesses. He allegedly paid off one witness after calling and texting her 128 times over a four-day period.

Combs has also been accused of attempting to influence a potential jury pool by getting his children to orchestrate social media posts and monitor the analytics. All of which contributed to the judge’s ultimate decision not to grant him bail – despite the $50m packaged proposed by his legal team which would see him under house arrest with 24-hour security.

It might be another six months away, but Combs’ trial is bound to continue dominating the headlines. 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.

While she does not face any allegations herself, Lopez is one such name. Since Combs’ arrest, she has been asked about his case 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. Lopez once described her relationship with Combs ‘emotionally exhausting’ and it looks like more than 20 years later it is coming back to haunt her again.