She Called Herself Bert — and Diddy Was Ernie. Here’s What Made Her ‘Super Nervous’

A woman who dated Sean “Diddy” Combs until his arrest on sex trafficking and racketeering charges in September 2024 testified at his federal trial Thursday, June 5, that months into their relationship, he introduced her something he called “hotel nights” — which bore resemblance to the “freak offs” detailed in the federal charges against him.

The woman, who is testifying under the pseudonym “Jane,” said she met Combs in 2020 while on a girl’s trip with a friend who was dating Combs at the time. Jane said her first date with Combs was in January 2021 at a Miami hotel, and that by May 2021, Combs began having conversations with her about his sexual fantasies involving other men and voyeuristic sex.

Prosecutors have alleged that like Casandra “Cassie” Ventura, his former girlfriend, Combs coerced Jane to participate in drug-fueled, multi-day sex marathons involving paid male escorts that he referred to as “freak offs” or, in Jane’s case, “hotel nights.” Combs’ attorneys have said Jane and Ventura willingly participated in the sexual encounters.

She said they gave each other nicknames: She was Bert and he was Ernie; like the Sesame Street characters. May 2021 marked the first time she had sex with a man while Combs watched, she testified — within hours, and to her surprise, Combs hired a man from an escort service, she testified. She testified that Combs’ assistants set up the hotel room for the encounter.

“I was super nervous,” she testified, breaking down in tears on the stand when recalling the experience.

She said she felt exhilarated after the first time — but then regretted it, because it set the tone for their relationship. Jane said their connection eventually became reliant on freak offs.

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Like Ventura, Jane testified that the encounters would sometimes last days. Prosecutors have said Combs exerted financial control over the women and threatened to release video of them participating in freak offs to keep them compliant. She said she and Combs drew up a verbal “love contract,” under which he would pay her rent, which was $10,000 a month. She testified that whenever she told Combs she didn’t want to participate in hotel nights, he would he would threaten to break up with her and to stop paying her rent. She said he became increasingly controlling as their relationship continued.

Jane, a single mother, testified that she was at the ready for Combs, who would sometimes give her less than a day’s notice for them to meet. She said she would make sure to have childcare lined up and to maintain her appearance, which included ensuring her nails and eyelashes were done, expenses she couldn’t always afford but that Combs would help fund. She said she really liked looking beautiful for Combs.

Ventura was the government’s star witness. She testified four days at the start of the trial, which is now in its fourth week. She told jurors about her turbulent on and off relationship with Combs that lasted more than a decade and how he physically abused her and once raped her. Ventura testified the freak offs left her feeling degraded.

Combs is facing sex-trafficking and racketeering conspiracy charges. He has pleaded not guilty.