Celebrity Celebrity Relationships Celebrity Friendships Why Leonardo DiCaprio and Kate Winslet Make the Perfect Date — and 5 Questions We'd Want to Ask One lucky person is getting the date of a lifetime with BFFs Leonardo DiCaprio and Kate Winslet -- and we have some suggestions on what they can ask the duo By Ale Russian Ale Russian Ale Russian is a contributing writer at PEOPLE. She has been working at PEOPLE since 2023. Her work has appeared in Women's World, First For Women, Biography.com and the Chicago Sun-Times. People Editorial Guidelines Published on July 27, 2017 02:27PM EDT Photo: Anthony Ghnassia/Getty Images for LDC Foundation One lucky person is getting the date of a lifetime with BFFs Leonardo DiCaprio and Kate Winslet. The Oscar-winning pair auctioned off a dinner date with the two of them during the Leonardo DiCaprio Foundation's (LDF) annual charity auction in St. Tropez, France Wednesday night — where they had a Titanic reunion with Billy Zane! The dinner will take place sometime in October or November in New York, and the lucky winner will get to sit down with the stars 20 years after they first met on the set of Titanic. DiCaprio and Winslet have had one of the longest running — and most adorable — friendships in Hollywood after they immediately hit it off on the set of the 1997 blockbuster. And although Winslet was initially concerned she would be distracted during filming by the dashing DiCaprio, the two never dated and instead quickly established a strong friendship that has continued through the decades. "The closeness and the strength of the friendship that we had is something a lot of my friends envy like mad," Winslet previously said. "But to me, he's just silly old Leo." FROM COINAGE: The Top 5 Most Expensive Movies of All Time Over two decades later, the two have been there for each other during successful awards season runs — with Winslet tearing up watching DiCaprio win his first Oscar in 2016 — and a reunion on screen for 2008's Revolutionary Road. DiCaprio even walked Winslet down the aisle during her 2012 wedding to current husband Ned Rocknroll. Celeb Quotes of the Day: Angelina Jolie, Nicole Kidman & More Now the two are giving the lucky bidder a chance to join their party — and we have some suggestions on what they can ask the A-list duo! Did Leo ever tell Kate to scoot over on that (huge!) door? Seriously, they both could've fit. There's even photographic proof! Paramount Does "My Heart Will Go On" ever randomly get stuck in their heads, too? It's so catchy and Céline Dion is a queen. There's no way they didn't also cry during her performance at the Billboard Music Awards this year. How often do people ask Leo to paint them like one of his French girls? It's one of Rose's most iconic lines in the film, but how often do people really say it to the actor? Does Kate ever send Leo approvals (or disapproval) of his girlfriends? He's dated some of the most beautiful women in the world — but what does Winslet think? Who's worse at texting? Our money's on DiCaprio.