Paris Hilton and Nicole Richie opened up about their turbulent dating pasts, sharing candid stories of heartbreak and betrayal during a new episode of Call Her Daddy. The longtime friends, who are currently promoting their Peacock special Paris & Nicole: The Encore, gave listeners an inside look at the challenges they faced in love during their younger years, including infidelity and public humiliation.
“Playa4Life” and Disneyland Drama
Nicole Richie recounted an unforgettable story about her first serious boyfriend, whose AOL screen name — “Playa4Life” — turned out to be a glaring red flag. Richie described being “devastated and shocked” when she discovered he had cheated on her, even learning about one incident that took place on the Disneyland ride Peter Pan’s Flight.
In a particularly 2000s twist, Richie explained how a conference call exposed her ex’s betrayal. After hearing rumors, she confronted him, only to be gaslit into denial. Fortunately, one of the women involved reached out directly: “She got on the phone with me and told me, ‘He said that you guys were broken up. I’m so sorry.’”
Richie admitted the experience left her “shook,” acknowledging that being cheated on was a painful but formative moment.
Public Humiliation and TMZ
Paris Hilton shared her own heartache, revealing she learned about one instance of infidelity through celebrity news site TMZ. “It obviously hurts, but also just like mad,” Hilton explained. “Just like, ‘How could you humiliate me like this?'”
For Hilton, the pain was compounded by the public nature of her dating life during the height of her career in the early 2000s. Unlike many people who could deal with heartbreak privately, Hilton’s relationships were often front-page news.
A Confrontation Gone Wrong
Richie also shared a more confrontational experience where she ran into a woman her partner was cheating with at a party. “I walked up to her–I don’t even know what I thought I was going to do,” Richie said, describing the tense moment. However, instead of a dramatic showdown, her plans quickly unraveled when the other woman’s friend dismissed her with a shooing gesture, sending Richie “flying across the party.”
From Drama to Healing
While the stories are laced with humor now, both Hilton and Richie reflected on how painful their experiences were at the time. Hilton, in particular, spoke about the challenges of having her dating life scrutinized by the media and how deeply it affected her.
“There would be a lot of nights I’d cry and I’d call my mom,” Hilton told Glamour in a previous interview. “I’d be like, ‘This is not even true.’”
Despite the trauma, Hilton shared how the experience shaped her into a stronger person: “After a while, I just realized these are people who don’t even know me. They’re just making stories up. The people who love and know me know the truth.”
Happily Ever After
Today, both Hilton and Richie are in much happier places. Hilton has been married to entrepreneur Carter Reum since 2021, while Richie recently celebrated her 14th wedding anniversary with musician Joel Madden. Both women now juggle careers, marriages, and motherhood, having moved on from the chaos of their younger dating years.
Their reflections on Call Her Daddy serve as a reminder of the growth that comes with time — and the strength it takes to overcome heartbreak, especially when the world is watching.
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