Leonardo DiCaprio has been happily dating his 27-year-old model girlfriend Vittoria Cerriti since 2023 but Lisa Rinna has now revealed that at some point, Leo “hit up” her daughters, Amelia and Delilah Hamlin – as did his best friend, Tobey Maguire.
Lisa, 62, made an appearance on Watch What Happens Live with Andy Cohen on February 25, 2026, and Andy asked if Leonardo – known for dating younger women – had ever “hit up” her daughters, Delilah, 27, and Amelia, 24, whom she shares with husband Harry Hamlin, 74.
“Yes. Didn’t happen, but yes,” Lisa answered, before making a face as if she wasn’t supposed to answer. “I mean, isn’t it a rite of passage?” joked Andy, as Lisa then continued: “And so did Tobey Maguire. But a lot of them have hit the girls [up], as you know.”
The conversation came about when Andy asked if it was true that a friend of the former Real Housewives of Beverly Hills star brought Leonardo and Tobey as guests to Lisa’s 50th birthday party; Lisa denied the rumors.
© Vivien KillileaAt the time, Leonardo would have been 39 and Tobey, 38. They have been best friends since the 1990s and have become part of a notorious group of actors, known for their love of nightclubs and yacht parties. The two have starred together onscreen in 1993’s This Boy’s Life, 2001’s Don’s Plum and 2013’s The Great Gatsby.
Amelia was 18 when she dated Scott Disick – who is 18 years older than her– for two years, and Lisa has gone on record as not fully supporting the romance. Amelia is now dating Nicolai Marciano, the heir to the Guess clothing empire, and a former classmate of her sister, Delilah.
© Penske Media via Getty ImagesDelilah dated Love Island UK star Eyal Booker for two years, and has been in a relationship with actor Henry Eikenberry since 2023, with the pair making their red carpet debut in June of that year.
Vittoria is an Italian model who made her runway debut in 2015 at the age of 17, and has walked for fashion giants like Chanel, Dolce & Gabbana, and Fendi on the catwalks of major fashion capitals, including Paris, Milan, and New York.
© Getty Images for AmendShe ended her marriage with New York-based DJ Matteo Milleri in June 2023, three years after they tied the knot in a charming ceremony held in Ibiza on June 1st, 2020, when she was just 21.
In February 2026 Vittoria, was selected as one of Winter Olympics official flagbearers; as a native of Brescia, Italy — located 90 minutes from Milan — the model presented the Italian flag to the Carabinieri’s elite honor guard, the Corazzieri.
In an Instagram post after the ceremony, she called the moment, “the greatest honor of my life.”
© Getty ImagesLeo and Vittoria first connected in 2023 in Milan, and one of their first public dates was in Santa Barbara, where they were seen enjoying iced coffee and ice cream. Only a month later she met Leo’s mom when they visited a museum in Milan, and in 2025 they both attended the Met Gala – although they did not walk the carpet together.
She and Leo have rarely spoken publicly about their romance, but she did tell Vogue France in 2025 that it “can be extremely annoying” when “as soon as you’re in a relationship with someone who has a larger following than you, you become ‘girlfriend of’—or ‘boyfriend of,’ for that matter”.
“It’s not nice to think that you can’t love whoever you want, because of the labels people need to stick on you,” she said, although she never named Leo.
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