Leonardo DiCaprio, 50, Reunites With Bachelor Party Pals While Girlfriend Vittoria Ceretti, 27, Is Away

Leonardo DiCaprio Reunites with ‘Pussy Posse’ Pals While Girlfriend Vittoria Ceretti Attends Event in Italy
By Ashleigh Gray for DailyMail.com
Published: 03:15 BST, 14 June 2025 | Updated: 03:15 BST, 14 June 2025

Leonardo DiCaprio, 50, enjoyed a boys’ night out in Los Angeles on Thursday, reuniting with his longtime friends—dubbed the “pussy posse” in the late ’90s—while his girlfriend, Vittoria Ceretti, 27, attended a Dolce & Gabbana event in Italy.

The Oscar winner was spotted with Tobey Maguire, Lukas Haas, Ethan Suplee, and Vincent Laresca at a dinner outing. DiCaprio kept a low profile in a black baseball cap, gray face mask, brown suede jacket, and a black T-shirt.

PICTURED: [Leonardo DiCaprio (center) with friends Tobey Maguire, Lukas Haas, and others outside a Los Angeles restaurant.]

The group, known for their wilder days in the ’90s, has maintained a close bond over the decades. Meanwhile, Ceretti joined actor Theo James in Capri for the launch of Dolce & Gabbana’s Light Blue perfume, posing elegantly aboard a yacht.

PICTURED: [Vittoria Ceretti at the Dolce & Gabbana event in Capri, wearing a sleek white ensemble.]

In a rare interview with Vogue France earlier this year, Ceretti opened up about her relationship with DiCaprio, revealing they met in Milan. “Who hasn’t seen Titanic? It’s an iconic film,” she said, referencing the 1997 classic released a year before her birth. She also emphasized trust in their age-gap romance: “Love protects and gives confidence.”

Ceretti has grown close to DiCaprio’s family, particularly his mother, Irmelin Indenbirken. Engagement rumors swirled last November, though neither has confirmed plans to marry. The pair were first linked in 2023 after being spotted on an ice cream date in LA and later dancing in Ibiza.

PICTURED: [DiCaprio and Ceretti at the 2025 Met Gala, smiling on the red carpet.]

While DiCaprio’s “pussy posse” days are long behind him, his loyalty to old friends remains. The actor, who won an Oscar for The Revenant (2016), continues balancing his career with low-key outings alongside high-profile relationships.

PICTURED: [Archive photo of DiCaprio and Maguire in their ’90s heyday.]

As Ceretti thrives in her modeling career, the couple’s transatlantic adventures highlight their jet-setting lifestyle—and DiCaprio’s knack for keeping his inner circle close, no matter the decade.