Hollywood might be a small town, but its dating pool is even smaller.
Lip gloss mogul and reality TV firestarter Lisa Rinna delivered a headline-grabbing confession while promoting her new memoir on Watch What Happens Live With Andy Cohen Wednesday night.
WATCH WHAT HAPPENS LIVE WITH ANDY COHEN — Episode 23032 — Pictured: (l-r) Andy Cohen, Lisa Rinna — (Photo by: Charles Sykes/Bravo via Getty Images) Bravo/Charles Sykes/Bravo via Getty Im
During a game of “Trait-ing, Truth and Falsehoods,” the Real Housewives of Beverly Hills alum, 62, found herself fielding a juicy question about whether a friend brought Leonardo DiCaprio and Tobey Maguire as surprise guests to her 50th birthday.
But after shooting down that rumor, Cohen pivoted to an even juicier question.
“Has Leo ever hit up either of your girls?” he asked of Rinna’s daughters.
“Yes,” Rinna replied without skipping a beat.
“And?” Cohen pressed.
“Didn’t happen. But yes,” she clarified.
Cohen then gave voice to what many were already thinking: “I mean, isn’t it a rite of passage?”
Rinna’s revelations weren’t done, she had one more name to add.
“And so did Tobey Maguire. Both, yeah,” she added, before noting that “a lot of ‘em have hit the girls up.”
Delilah Belle Hamlin, Amelia Gray and Lisa Rinna at the FRAME & Amelia Gray Dinner on November 18, 2025 in Los Angeles, California. (Photo by River Callaway/WWD via Getty Images) River Callaway/WWD via Getty Images
It’s unclear how old her daughters—Delilah Belle, 27, and Amelia Gray, 24—were at the time of the alleged overtures. But DiCaprio, 51, has built a tabloid legend around dating significantly younger women.
The Oscar winner has romanced a string of famous models and actresses, including Gisele Bündchen, Bar Refaeli, Blake Lively, and Camila Morrone. But the relationships tend to fizzle out well before his partners turn 30.
Maguire, 50, has appeared to adopt a similar dating pattern since splitting with his ex-wife Jennifer Meyer. He has been linked to younger models, including Tatiana Dieteman, 33, and Lily Chee, 22, and was recently photographed alongside 20-year-old influencer Mishka Silva.
DiCaprio and Maguire have been longtime friends, moving in the same Hollywood circles since starring together in the 1993 film This Boy’s Life.
Rinna isn’t unfamiliar with her daughters being linked to older men. Amelia previously dated Scott Disick—18 years her senior—from 2020 to 2021.
Rinna publicly side-eyed the relationship at the time and celebrated its demise with a rose-hued smiley face emoji on Instagram.
Disick, for his part, has continued dating younger women since his split from Amelia, including model Rebecca Donaldson, 30, and Too Hot to Handle alum Holly Scarfone, 27.
In Hollywood, the men may age, but the dating pool rarely does.
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