The “Leo Law” of Hollywood dating—where the Oscar winner rarely dates women over 25—just got a new, uncomfortable chapter.
During a chaotic appearance on Watch What Happens Live this week, reality TV icon Lisa Rinna didn’t just spill tea; she shattered the pot. In a segment designed to expose truths, Rinna confirmed that Leonardo DiCaprio (51) and his best friend Tobey Maguire (50) have both pursued her daughters.
The revelation left host Andy Cohen joking about Hollywood “rites of passage” while fans online are debating the line between flattering and “creepy.”
The “Truth and Falsehoods” Confession
The moment arrived during a game called “Trait-ing, Truth and Falsehoods,” where Cohen read statements about Rinna’s life to see if she would confirm or deny them.
When asked if the Titanic star had ever “hit up” her daughters—Delilah Belle Hamlin (27) and Amelia Gray Hamlin (24)—Rinna didn’t hesitate.
“Yes,” Rinna said, before quickly clarifying the outcome. “Didn’t happen. But yes.”
She didn’t stop at DiCaprio. In the same breath, she threw another A-list name into the mix, revealing that the original Spider-Man was also part of the equation.+1
“And so did Tobey Maguire,” she added nonchalantly. “But a lot of ’em have hit the girls [up], as you know.”
A “Rite of Passage”?
The studio audience reaction was a mix of shock and laughter, but the internet response has been sharper. Cohen attempted to diffuse the tension by cracking a joke: “I mean, isn’t it a rite of passage?”
But for many, the timeline raises questions. While Delilah is now 27, Amelia Gray is just 24—fitting perfectly into the “under 25” dating pattern that has followed DiCaprio for decades.
This isn’t the first time the Hamlin sisters have attracted older Hollywood suitors. Amelia Gray famously dated Scott Disick (now 40) when she was barely out of her teens, a relationship that played out awkwardly on The Real Housewives of Beverly Hills.
The “Wolf Pack” Rides Again
DiCaprio and Maguire have been best friends since the 90s, often seen partying together on yachts and at exclusive clubs. Rinna’s claim that both men pursued her daughters reinforces their reputation as Hollywood’s inseparable duo, even in their dating lives.+1
Currently, DiCaprio is linked to 27-year-old model Vittoria Ceretti, while Maguire has been single since his split from Jennifer Meyer.
Neither actor has commented on Rinna’s claims, but if history is any indication, they likely never will.
The Bottom Line
Lisa Rinna has made a career out of “owning it,” and this latest admission proves she has zero filters left. While she insists nothing “happened” between the actors and her daughters, the mere fact that two 50-year-old icons allegedly slid into their DMs is the kind of Hollywood lore that keeps the rumor mill spinning.
Is this a harmless Hollywood hustle or a “red flag” for the A-listers? Sound off in the comments.
Live from the heart of Los Angeles, Chloe Baxter brings you the hottest scoops from the Hollywood Hills. With over a decade of experience covering red carpet premieres, exclusive after-parties, and viral celebrity scandals, Chloe has her finger on the pulse of Tinseltown.
Known for her sharp wit and deep industry connections, Chloe doesn’t just report the news—she uncovers the stories behind the headlines. From the latest Royal Family drama to breaking updates on music’s biggest stars, she is Newskilo’s go-to source for all things pop culture. When she’s not breaking a story, Chloe can be found hunting for the best iced coffee on Sunset Boulevard.