Diddy’s “Freak-Off” Flirtation: Cassie’s Ovulation Revelation Unpacked
Could anything be more eyebrow-raising than a celebrity ex dropping ovulation status mid-phone-sex proposal? That moment made headlines when deposition transcripts from Cassie Ventura’s lawsuit against Sean “Diddy” Combs revealed she bluntly told her ex she was ovulating after he asked to “freak-off” during a 2016 dinner in New York City. According to TMZ‘s May 15, 2025 report, lawyers playing recorded calls in Manhattan Supreme Court showed Cassie keeping her cool while Diddy, guest of honor at L’Avenue, leaned in for some risque negotiation. Page Six corroborates that the exchange wasn’t your average PDA—Diddy explicitly requested intimate phone play, Cassie answered with medical honesty, and then agreed to kiss him when he swung by her table.
If you thought the rest of the lawsuit was dry legalese, think again. Cassie’s team introduced these candid clips to buttress claims of sexual battery and unwanted advances from the mogul. Diddy’s defense counters that every moment was consensual, citing these same calls as proof. Yet the delicious irony is that the most mundane detail—a woman disclosing her menstrual cycle phase—became the trial’s spicy headline. Rolling Stone notes that “ovulation” hasn’t graced tabloids like this since the glory days of Wild ’90s celebrity overshare. Meanwhile, People Magazine reminds us that this drama speaks to larger conversations about consent in high-power relationships.
Unpacking the transcript, you’ll find Diddy casually prompting Cassie for erotic dialogue (“You wanna freak now?”), punctuated by her frank biology lesson (“Yeah, I’m ovulating”). They seal the deal with a quick smooch, all captured on Diddy’s own voice memos. Legal experts tell People this recording cuts both ways: it shows enthusiastic compliance, but also highlights power imbalances—Cassie felt pressured under the spotlight of his superstar status. Through this lens, the courtroom scene becomes less about kissing and more about accountability in celebrity culture.
Love it or hate it, this little nugget of TMI is now public record, fueling every late-night monologue and Twitter thread about how consent conversations should—or shouldn’t—sound. Whether you side with Cassie’s candid call or Diddy’s claims of mutual flirting, the takeaway is clear: even A-list romances come with awkward, irrepressibly human moments. So there you have it—another celeb scandal turned courtroom reality show. Nothing shocking here, folks. Let’s all act surprised.
Sources: Celebrity Storm and TMZ, Page Six, People Magazine
Attribution: Creative Commons Licensed
