Diddy and Cassie Timeline: Inside Their Decade-Long Relationship
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Cassie Ventura gave compelling testimony in ex-boyfriend Sean “Diddy” Combs‘ federal sex trafficking case. Combs has denied all allegations in the case and has pled not guilty. In Touch has her most shocking quotes from court.

How Did Cassie and Diddy Meet?

Cassie met Diddy when she was 19, and he signed her to a 10-album deal. She claimed in court that she recorded nine albums but never released any of them. She said she was “enamored by him” in the beginning and said, “We were just having a good time.”

“This lifestyle was much different,” Cassie explained. “He had assistants at his beck and call. He could get anything done quickly. He had respect from everyone, and he traveled quite a bit.”

Cassie Claimed She Got Abused for ‘Making the Wrong Face’

Their romance started on a trip to Miami when they took a “blue dolphin” ecstasy pill on a boat. Cassie went on to describe Diddy as having extreme mood swings, where if she would “make the wrong face, and the next thing I knew, I was getting hit in the face.”

Cassie Ignored Warning Signs About Diddy Out of ‘Love’

The singer said Diddy’s security kept an eye on her, admitted that the mogul was “insanely jealous” but moved to Los Angeles to be with him “because I was in love and I wanted to be near him.” She also testified that she had her own apartment and Diddy had keys to it.

Cassie Recalled How She Was Introduced to ‘Freak Offs’

“He described it as a fantasy he had where he would want to see me having sexual interactions with another male so he could watch,” Cassie testified, noting she was 22 years old at the time.

She ended up having intercourse with a male sex worker.

“I was high, so I didn’t feel much,” she said. “Did this really happen to me? I didn’t know what was going to happen after that, if we were going to do it more frequently. I said yes to more, I didn’t want to make him upset or angry,” Cassie testified.

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Shareif Ziyadat/FilmMagic

Diddy and Cassie

Cassie Went Into Detail About Diddy’s Alleged ‘Freak Offs’

Diddy’s ex described the sex-fueled parties known “freak offs” taking up a “big chunk of” her life. Cassie said they would last for days and included her staying up for days on end, drinking and using drugs and having sex with “strangers.”

“I had to look a certain way during freak offs,” she said, describing how she spent a lot of time getting prepared for the freak offs that started out occasionally and then turned weekly.

“I felt pretty horrible about myself. I felt disgusting. I felt humiliated,” Cassie shared about being part of the “freak offs,” adding, “I didn’t have the words to show how horrible I felt. I couldn’t talk to anyone about it.”

Cassie Claimed Diddy Was Controlling About Her Looks

“Appearance was very important to him — my appearance,” Cassie explained on the stand, saying Diddy would make comments about everything from her nails to her hair, as well as discussions about breast implants.

“My self-worth took a hit for the entirety of the relationship, just trying to establish who I was, who I wanted to be, who I was allowed to be,” Cassie added.

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Emma McIntyre/Getty Images

Diddy and Cassie

Cassie Explained Diddy’s Massive Supply of Baby Oil

Federal authorities seized 1,000 bottles of baby oil and lubricant from Diddy’s Miami and Los Angeles homes during March 2024 raids. During her testimony, Cassie explained the substance’s use during “freak offs.”

“Sean wanted it heated, and he wanted it to be glistening, so we applied every five minutes,” she said about herself and other participants.

Cassie went on to recall how the there was “a pool filled with baby oil” during a particular “freak off” at the Montage Beverly Hills.

“If Sean wanted it to happen, that was what was going to happen, there was no way around it,” she continued. “We used 10 bottles of baby oil, regular size.”

Cassie went on to describe how the “freak offs” occurred at Diddy’s houses and hotels across the world, including Miami, Los Angeles, New York City, Las Vegas, Atlanta, Ibiza, Spain and Turks and Caicos.

Cassie Called Diddy a ‘Scary Person’

Cassie described going out of her way to appease her then-boyfriend at all times. “I didn’t want him to be upset or not trust me,” she testified. “He was a scary person, he would be violent.”

Cassie Testified That Diddy Had Guns

Cassie testified that she saw handguns in Diddy’s home in Miami and Los Angeles, as well as his New York and New Jersey residences, per CNN.

The Connecticut native also recalled a time where she and Diddy were having a “freak off” at his L.A. home when a security guard, D-Roc, told the rapper that his rival, Death Row Records cofounder Suge Knight, was at a nearby diner.

“They quickly packed up and drove down there,” she testified. “I was crying, I was screaming, ‘Don’t do anything stupid.’ I just was really nervous for them, I didn’t know what it meant, what they were going to do,” Cassie said, while The New York Times reported she was handed a gun to put in her purse. The outlet said Cassie testified it was not the only time she was asked to handle such a weapon for Diddy.

Cassie Recalled Allegedly Being ‘Raped’ by Diddy

During her second day of testimony on May 14, 2025, the singer said the duo went out to dinner in Malibu in August 2018. Cassie told the court she believed it was for a “closure conversation,” since she had already begun dating her now-husband, Alex Fine.

While the rapper was in a good mood over the meal, things went awry when he drove her home.

“And then he raped me in my living room,” Cassie testified. “I just remember crying and saying ‘no,’ but it was very fast,” adding she was unsure if Diddy noticed that she was in tears.

Diddy Allegedly Apologized for Cassie Getting Infections During ‘Freak Offs’

During day 2, text messages were shown between Cassie and Diddy showing the singer talking about sores on her tongue. She testified she believed it was from the “freak offs.” Diddy reportedly wrote, “I’m sorry,” in one message.

Cassie said she had persistent urinary tract infections when she and Diddy were having “freak offs” and that she would still perform despite her pain. She said she was addicted to opiates “off-and-on” and would take them to come down from ecstasy and other party drugs.

“Opiates made me feel numb, which is why I relied on them so heavily,” she testified, later adding, “I didn’t want to feel what was actually going on in my mind, in my life, in real time. It was just an escape for me.”

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Jim Spellman/Getty Images for Deleon Tequila

Cassie and Diddy

Cassie Claimed Diddy Got Physical During ‘Sex Club’ Visits

Cassie also spoke about going to “sex clubs” with Diddy, saying she felt pressured and uncomfortable at the clubs. She accused Diddy of having “put his hands on me” during one “freak off” with male escorts. “He would grab me up,” she said. “Push me down. Hit me in the side of the head. Kick me. You name it.”

Cassie Claimed Diddy Threatened Her With the Release of ‘Freak Off’ Videos

Cassie said that Diddy threatened to release “freak off” videos of her in 2011 when he found out she was seeing rapper Kid Cudi, real name Scott Mescudi.

“He told me about videos that he had that he was going to release, and that he was going to hurt Scott and I,” she told the court, saying the videos were of “freak offs.”

Cassie and Diddy later flew to New York, when he allegedly wanted a “freak off.”

“At that point, whatever was going to make him not be angry at me and threatening me, I was willing to do,” she testified. “I just didn’t want to feel scared anymore. It was the one thing he made me feel like I was good at.”

Cassie read a 2017 text message she sent to Diddy where she told him “nothing good” came out of the ‘freak offs.” She added, “You treat me like you’re Ike Turner,” referring to Tina Turner’s abusive ex-husband. Cassie said she compared their relationships because Diddy was “abusive and controlling” toward her.

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ANGELA WEISS/AFP via Getty Images

Diddy and Cassie

Cassie Testified That She Was Afraid to Leave Diddy

“I didn’t have the resources I needed to get out and move, to get out and not have anybody stop me,” she said. “I understood Sean’s capabilities, his access to guns, and the threats that he made prior to that.”

When her mother reached out to Cassie to check on her, she said she was afraid to tell her about the abuse.

“I didn’t tell my mom the truth because I was ashamed, but I also felt like at that point I didn’t know what was going to happen,” she testified. “I didn’t want to put my mother in danger of knowing anything of that magnitude.”

Cassie Claimed She Was Left With a Scar From a 2013 Attack

Cassie claimed to have been awakened in 2013 by Diddy yelling at several of her friends inside her apartment, ahead of the group traveling to a music festival. A fight ensued over the mogul claiming she should have been packing instead of sleeping, when one of the friends jumped on Diddy “because he was trying to attack me.”

Cassie testified that she hit her eyebrow on the side of a bed after Diddy threw her down. She said it resulted in a “pretty significant gash” and that she needed to see a plastic surgeon to suture the wound.

The singer said she later texted Diddy a photo of her injury, writing, “so you can remember.” Cassie claimed Diddy replied with the message, “You. Don’t know. When to. Stop. You have pushed IT Too far. And continue to push. Sad.”

Cassie Revealed She Received $20 Million From Diddy to Settle Her Civil Suit

For the first time, Cassie revealed that she received $20 million from Diddy after they settled a civil suit she brought against him in November 2023. At the time, Cassie claimed in her lawsuit that she was the victim of rape and physical abuse, alleging that she “endured over a decade of violent behavior and disturbed demands.”

Cassie and Diddy settled the lawsuit out of court on November 17, 2023, one day after her filing.

The terms of the deal were kept under wraps. Diddy’s lawyer, Ben Brafman, emphasized at the time that a settlement was in “no way an admission of wrongdoing.”

“Mr. Combs‘ decision to settle the lawsuit does not in any way undermine his flat-out denial of the claims,” the attorney said in a statement. “He is happy they got to a mutual settlement and wishes Ms. Ventura the best.”

How Long Did Cassie and Diddy Date?

The former couple was together from 2007 to 2018.

Why Is Diddy on Trial?

The former music mogul was arrested on September 16, 2024, following a lengthy federal investigation.

Diddy was charged in a three-count indictment with racketeering conspiracy, sex trafficking and transportation to engage in prostitution. The indictment alleged Diddy abused, threatened and coerced women and others around him to “fulfill his sexual desires, protect his reputation and conceal his conduct.”

The complaint claimed Diddy was verbally, physically and sexually abusive.

“We will not shy away from the things he did, but we will not own the things he did not do,” Diddy’s lawyer, Teny Geragos, told jurors in her opening statement in his trial on May 12, 2025, per NBC News. “He is physical, he is a drug user, you may know of his love of baby oil. Is that a federal crime? No!”

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