Late rap legend Tupac Shakur had a string of high-profile girlfriends over the years but managed to keep his A-list lovers secret.
Many of his famous girlfriends never spoke about their relationships with the rapper, while others waited until many years after his death to confirm the romance.
The music superstar, who died in a shooting in 1996 aged 25, is now believed to have had a steamy affair with Whitney Houston and broke Madonna's heart.
He also found the time to get married and divorced, and date music industry royalty.
Tupac dated Madonna for more than a year after being set up by pal Rosie Perez at the Soul Train Awards in 1993.
However, they managed to keep the romance totally under the radar and it wasn't confirmed until 2015.
Madonna let slip about her relationship with Tupac during an interview with US shock jock Howard Stern, telling him the pair dated and the rapper got her "all riled up about life in general".
However, little else was known about the romance until a bombshell dropped in 2017 when a letter from Tupac to Madonna revealed he broke up with her because of her race.
The note, believed to have been written while he was in prison in 1995, told the singer that their romance had to end as it wouldn't look good for his career.
Dated January 15 1995, the letter published by TMZ explained: "Can u understand that?
"For you to be seen with a black man wouldn't in any way jeopardize your career.”
"But for me at least in my previous perception I felt due to my 'image' I would be letting down half of the people who made me what I thought I was.”
"I never meant to hurt you."
The stunning revelation that Tupac bedded music legend Whitney Houston didn't emerge until after her death aged 48 in 2012.
Her ex-husband Bobby Brown made the confession about his wife's affair in his 2016 memoir Every Little Step, claiming she cheated on him with Tupac during their marriage.
In the book, Brown claimed Whitney and Tupac hooked up after they worked together but gave no further detail.
The New Edition star claimed his ex-wife did her “share of cheating” with “quite a few of the producers and artists”, but only named TUpac.
Jada Pinkett Smith
Although they were never lovers, Jada had a strong relationship with Tupac that nearly became romantic.
However, Jada insisted there was no "physical chemistry" between them - even when they tested it out by kissing.
Speaking to DJ Howard Stern in 2015, Jada explained: "When you have two young people that have very strong feelings, but there was no physical chemistry between us at all, and it wasn’t even just for me.
"It was him too."
Tupac was dating music industry royalty Kidada Jones, daughter of legendary producer Quincy Jones, at the time of his death in 1996.
They got together following the collapse of his brief marriage to Keisha Morris in 1995, and it initially got off to a bumpy start after Kidada ignored his advances because he'd previously dissed her dad.
However, after the rapper apologised, they exchanged numbers and embarked on a whirlwind romance.
He's said to have told his mum: "I love her. She's going to be my wife; she's having my children."
They got a house in together in Calabasas, but the romance was cut short by tragedy as Tupac was murdered just four months after they started living together.
In Quincy Jones' 2001 book, Kidada wrote of Tupac's death: "He and I lived together for four months and then he was murdered in Las Vegas in 1996. It was the most horrible thing that ever happened to me."