Lisa Rinna disclosed that both Leonardo DiCaprio and his longtime friend Tobey Maguire once showed romantic interest in her daughters. The revelation came during a February 2026 interview, as Rinna addressed claims about the famed actors’ past attempts to date her daughters Amelia and Delilah Hamlin.
Actors’ Interest in Rinna’s Daughters Surfaces During Interview
In a conversation on Watch What Happens Live with Andy Cohen on February 25, 2026, Lisa Rinna, 62, was asked if Leonardo DiCaprio, known for dating younger women, had ever pursued her daughters Delilah, 27, and Amelia, 24. Both girls are the children she shares with Harry Hamlin, 74. Rinna confirmed the claims without hesitation, responding, “Yes. Didn’t happen, but yes,” and then added with hesitation.
Host Andy Cohen lightheartedly remarked,
“I mean, isn’t it a rite of passage?”
before Rinna continued:
“And so did Tobey Maguire. But a lot of them have hit the girls [up], as you know.”
The exchange confirmed that both actors had shown interest, though no relationships developed.
Past Party Rumors and Actor Friendships
The conversation originated when Cohen asked about rumors that a friend from Lisa Rinna’s social circle had brought both Leonardo DiCaprio and Tobey Maguire as guests to her 50th birthday party. Rinna denied this, clarifying that the accounts were not accurate.
At that time, Leonardo was around 39 years old and Tobey was 38. The pair has been close friends since the 1990s, frequently appearing together socially. They belong to a well-known circle of actors recognized for their affinity for nightclubs and luxury yacht gatherings. Their professional collaborations include “This Boy’s Life” (1993), “Don’s Plum” (2001), and “The Great Gatsby” (2013).
Background on Amelia and Delilah Hamlin’s Relationships
Amelia Hamlin gained public attention dating Scott Disick, who was eighteen years her senior. The relationship lasted two years, though Lisa Rinna was openly skeptical of it. Currently, Amelia is in a relationship with Nicolai Marciano, heir to the Guess clothing brand, who was also a former classmate of her sister Delilah.
Delilah Hamlin previously dated Eyal Booker, known for “Love Island UK,” for two years. Since 2023, she has been in a relationship with actor Henry Eikenberry, the couple making their red carpet debut that June.
Details About Leonardo DiCaprio’s Girlfriend Vittoria Cerriti
Since 2023, Leonardo DiCaprio has been dating Italian model Vittoria Cerriti, who is 27 years old. Vittoria began her modeling career with a runway debut in 2015 at age 17 and has represented prestigious fashion houses including Chanel, Dolce & Gabbana, and Fendi across global fashion centers such as Paris, Milan, and New York.
Vittoria finalized her divorce from New York-based DJ Matteo Milleri in June 2023, three years after their wedding in Ibiza in 2020, when she was just 21. Highlighting her prominence beyond modeling, Vittoria was honored as one of the official flagbearers for the Winter Olympics in February 2026. Hailing from Brescia, Italy—near Milan—she presented the Italian flag to the Carabinieri’s elite honor guard, the Corazzieri.
In an Instagram post following the ceremony, she described it as
“the greatest honor of my life.”
The Progression of Leo and Vittoria’s Relationship
Leonardo and Vittoria first met in Milan in 2023, shortly afterward appearing in public together during a casual outing in Santa Barbara where they enjoyed iced coffee and ice cream. Just a month later, Vittoria met Leonardo’s mother during a museum visit in Milan. The couple attended the 2025 Met Gala, though they did not walk the red carpet as a pair.
Though their romance is largely private, Vittoria spoke to Vogue France in 2025 about the difficulties of dating a high-profile partner. She remarked 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.”
She also shared,
“It’s not nice to think that you can’t love whoever you want, because of the labels people need to stick on you,”
though she did not explicitly name Leonardo.
The Social Circles Around the Hamlin Sisters and Hollywood Figures
The relationships and social interactions between the Hamlin sisters and prominent actors such as Leonardo DiCaprio and Tobey Maguire reflect the close-knit nature of Hollywood’s elite circles. The fact that both actors approached Lisa Rinna’s daughters at various points shows how these families often intersect through friendships, careers, and social events.
Lisa Rinna’s recent disclosures add a new layer to the public’s understanding of these connections, given the ongoing fascination with Leonardo DiCaprio’s private life and his history of high-profile relationships.
Significance of the Revelation for Celebrity Relationships
Lisa Rinna’s revelation bridges the worlds of Hollywood stardom, celebrity offspring, and fashion notoriety, highlighting complex dynamics in celebrity dating culture. The intertwined histories of the actors and her daughters reveal the merging of personal and professional networks that often fuel media speculation.
The disclosure also sheds light on Tobey Maguire’s quieter role within this social landscape, often overshadowed by Leonardo DiCaprio despite their long-standing friendship and shared past. For fans and media observers, these details enhance insight into Hollywood’s relational intricacies.
Looking ahead, the focus will likely remain on how Leonardo DiCaprio and Vittoria Cerriti’s relationship develops, along with the personal lives of the Hamlin sisters as they navigate romance and media attention within the public eye.
