15 Must-See #WhatsInMyBag Views

1996 — Kate and Leo meet on the set of Titanic.

We all know and love the friends-to-lovers trope, but Winslet and DiCaprio are the poster children for the lovers-to-friends trope. The actors met while playing love interests in Titanic. Although their onscreen relationship has never come to fruition offscreen, Winslet says the pair immediately clicked as friends.

“He was just very free with himself, and he had this effervescent energy that was really magnetic,” she said in a 2023 Titanic re-release featurette. “And I remember thinking, 'Oh, this is gonna be fun. We're definitely gonna get along.' And we just really did. We just really did.”

1998 — They walk the red carpet together at the Golden Globes.

If you Google “young Leonardo DiCaprio and Kate Winslet,” there’s a 99 percent chance the first pictures will be from this red carpet, mostly because Winslet’s look is sooo ’90s. In an interview with ET, DiCaprio says they absolutely came together, but clarifies that they’re “good buddies.”

2008 — They join forces on screen again.

The first movie Winslet and DiCaprio did together post-Titanic was Revolutionary Road, where they play another couple who doesn’t work out because one of them dies by the end of the movie (quite a specific niche to fall into, no?). Unlike Jack and Rose, their characters in Revolutionary Road have a tense relationship, which Winslet said made working on the film “an immensely emotionally challenging experience” for both of them.

“There’s just a trust factor there. We both know that we have the best intentions for each other, but we also know that we can push each other’s limits,” DiCaprio said in an interview for the film. “There’s probably no other actress out there that I would feel as comfortable attacking, and I know she can give every bit of it right back to me.”

2009 — Kate shouts Leo out in her Golden Globes acceptance speech.

Winslet won a Golden Globe for Best Actress in a Motion Picture — Drama for her role in Revolutionary Road. She gave a heartfelt speech that included some very kind words for her costar and best friend.

“Leo, I’m so happy I can stand here and tell you how much I love you and how much I’ve loved you for 13 years. Your performance in this film is nothing short of spectacular. I love you with all my heart, I really do,” Winslet said. DiCaprio blew her multiple kisses as she spoke. Feel free to join in the audience’s aww-ing; this moment is just too sweet.

2012 — Leo walks Kate down the aisle.

A source told Us Weekly that DiCaprio walked Winslet down the aisle at her wedding to Ned Rocknroll (whose real name is Edward Abel Smith, in case you were worried) in December 2012.

2016 — Kate Winslet cries at Leonardo DiCaprio’s Oscar speech.

When Leo finally won his first Oscar in 2016 for The Revenant, the camera cut to Kate tearing up and clasping her hands in front of her face during his speech. She was also spotted giving him a quick, friendly kiss on the cheek during a commercial break.

2017 — They have dinner in Saint-Tropez.

Pictures blew up over the internet of DiCaprio and Winslet “vacationing” together in Saint-Tropez, but Winslet later revealed that they were there on business. “Leo did his annual fundraiser for the Leonardo DiCaprio Foundation. He and I went together and we auctioned off dinner with Jack and Rose and actually raised $1.35 million. It was extraordinary,” she told E!.

2021 — They reunite for the first time since the pandemic hit.

Winslet revealed that she cried the first time she saw DiCaprio after the pandemic began. “I’ve known him for half my life! It’s not as if I’ve found myself in New York or he’s been in London and there’s been a chance to have dinner or grab a coffee and a catch up,” she told The Guardian. “We haven’t been able to leave our countries. Like so many friendships globally, we’ve missed each other.”

2023 — Winslet reflects on her friendship with DiCaprio on Titanic’s re-release featurette.

Kate Winslet revealed that when she and Leonardo DiCaprio call each other, they pick up the phone right away. “There’s no like, ‘Hang on, I’ll call you tomorrow.’ It's instant,” she told ET Online. Think about that next time your bestie gives you an impromptu ring.

The actress also got a bit more sentimental about her long-standing friendship with Leo. “You know, if you think about it, in the world that we live in now, to have friendships that bind you, and that shared history, it’s really something,” she said.

One thing’s for sure: if the Titanic had actually gone down in 1997, Kate would have definitely made room for Leo on that dang door.

November 4, 2024 — Kate Winslet Praises Leonardo DiCaprio and Revolutionary Road

In an interview with Vanity Fair, Kate Winslet recalls just how difficult it was bringing Revolutionary Road to life. The story follows Frank and April Wheeler as they struggle with both the cracks in their marriage and their 1950s suburban reality.

"The thing that people say is, 'You got to work with Leo again.' Then they go off on the whole Leo tangent, which I totally understand," she says. "But Revolutionary Road — f—king hell, it just knocked us all sideways. Unbelievably difficult material. I was very proud of that film and what Leo and I were able to create as Frank and April. It was so brutal."

November 19, 2024 — Leonardo DiCaprio Supports Kate Winslet's Lee

Leo made a special screening of Kate Winslet's Lee even more special by showing up to support her! The two were photographed hugging in front of the poster and it's truly the push I needed to get through the week :').