Cassie Ventura has taken the stand in ex-boyfriend Sean “Diddy” Combs’ sex trafficking trial and made some shocking revelations about her decade-long tumultuous relationship with the rapper. During her May 2025 testimony, she detailed the start of her relationship with Diddy and discussed how their 17-year age gap allegedly helped him prey on her sexually. Diddy has denied all allegations against him and pleaded not guilty to all charges. In Touch breaks down how old Cassie was when she began dating Diddy and more.

How Old Was Cassie When She Dated Diddy?

Cassie and Diddy first met in 2009, when she was 19 years old and he was 37 years old. He signed the Connecticut native to his Bad Boy Records label, which produced her debut and only studio album, Cassie, in 2006.

Though Diddy was in an on-off relationship with Kim Porter when he met Cassie, the pair later called it quits for good in 2007. He and Cassie sparked dating rumors soon after the split. At the time, Cassie was about 21 years old.

In her testimony, Cassie said that Diddy allegedly introduced her to oral sex shortly after her 21st birthday.

“Sean taught me how. He gave me oral sex, I did not reciprocate — I just went home,” she said. “I heard about it from him. He made me feel crazy for not reciprocating but I didn’t understand and I was in a relationship with someone else.”

She continued, “I was so young and I didn’t have the vocabulary and was just trying to understand it. I was sexually inexperienced. Leaving him was always confusing. I felt special and not a lot of people got that time.”

She also said that she was barely 22 years old when Diddy first asked her to participate in his “freak offs.” Cassie admitted to feeling “confused” and “nervous” about the sex parties, but she “loved him very much.” She said that she felt like she couldn’t say no to the parties because “there were blackmail materials to make me feel like if I didn’t do it, it would be held over my head in that way or these things would become public.”

Were Cassie and Diddy Ever Married?

Cassie and Diddy were never married, but their on-off relationship continued until 2018.

“They are indeed no longer together and haven’t been for months,” Cassie’s rep confirmed in October 2018 after the record producer was spotted with model Jocelyn Chew.

Five years after the romance ended, Cassie filed a $30 million lawsuit against her ex in November 2023, claiming that she was raped, sexually assaulted and physically abused by Diddy throughout their relationship. However, Diddy denied the allegations, and the lawsuit was settled just one day later.

Cassie Drops Shocking Bombshells in Diddy Trial Testimony

Cassie reiterated her abuse claims in her testimony. For example, she alleged that Diddy had extreme mood swings and that, during a trip to Miami, if she would “make the wrong face, and the next thing I knew, I was getting hit in the face.”

The Empire star also said that Diddy controlled her appearance and that his security kept a close eye on her.