Sean “Diddy” Combs wrote love letters to Cassie Ventura while he was high on drugs with his girlfriend “Jane Doe”, the mogul’s trial has heard.
She made the admission on Wednesday under cross-examination by defense attorney Teny Geragos, who asked if she remembered Diddy writing the notes for Ventura, whom he dated from 2007 through 2018, while he was on drugs. She simply replied, “Yes.”
Doe, who dated Diddy from 2021 through 2024, recalled the rapper describing Ventura as “one of his greatest loves.” Ventura took the stand for a week in May, testifying about her turbulent 11-year relationship with Diddy, which included physical abuse and sex marathons with male escorts.
In yet another yes-no question, Geragos asked whether another ex, Gina, “tormented” his relationship with Ventura. “Yes,” Doe once again replied.
In an earlier line of questioning, Geragos asked Doe whether it was fair to say Gina had a “tendency for dramatics,” and Doe agreed. In a September 2023 text read in court, Doe described his relationship with Gina as a “toxic cycle for you and it bleeds into our relationship.” She told the court that she thought Diddy and Gina “had a lot of public problems.”
Federal prosecutors have charged the music mogul with five counts of racketeering conspiracy, transportation to engage in prostitution and sex trafficking. He has pleaded not guilty. The love letter revelation was one of several eye-opening moments during Wednesday’s testimony.
- Doe recalled buying whips, lube, and shorts that both Diddy and the escort would wear during “hotel nights.”
- For her birthday in 2023, Doe asked Diddy to send $15,000 to pay for an outfit and a private room at a Los Angeles restaurant.
- The rapper also gifted Doe a Van Cleef necklace and bracelet for her birthday that year, she testified.
- In March 2023, the mogul spent $55,000 on a trip with Doe to Turks and Caicos, according to Geragos.
- The government is trying to remove a juror due to a “lack of candor with the court” — a move that Diddy’s defense team called “a thinly veiled effort to dismiss a Black juror” and noted they plan to object to the removal.

Around this time in their relationship, Doe told Diddy she needed to take a mental break from their relationship and encouraged him to get sober, she recalled.
“I would want him to eat good foods, vitamins, get off his drugs,” she said, adding that she sent him recipes and encouraged him to meditate and do yoga. Diddy agreed to be sober for 30 days — but first he wanted a sobriety party, Doe testified.
This event entailed a “hotel night” that spanned 12 to 18 hours at the L’Ermitage Beverly Hills. Doe, who was sober during the sex marathon, slept with three escorts that night despite getting sick after sleeping with the second.
“You agreed to it?” Geragos asked, referring to the sobriety party, to which Doe replied: “Unfortunately, yes.”
Pressed on whether she regrets that decision now, Doe told the court: “I resent him for knowing how much I loved him and knowing I couldn’t say ‘no.’”
Doe’s cross-examination continues Thursday.