Since Titanic arrived in theaters over two decades ago, the public has been shipping Leonardo DiCaprio and Kate Winslet together. Given Leo’s reputation for dating much younger women, typically models, many fans have given up hope that he and Kate will ever turn their relationship romantic.
But with recent reports that Leonardo is dating a teenager, many are wondering how Kate feels about the situation. Kate and Leo have been friends for decades, and she’s always vocally been supportive of him in public interviews, but his latest girlfriend may be changing her perspective. Here’s everything we know about Kate’s feelings towards Leonardo’s controversial dating history.
Leonardo DiCaprio & Kate Winslet Have Been Friends For Decades

Leonardo and Kate first met in 1996 when filming James Cameron’s Titanic, which released the following year and catapulted the young actors into fame. Though they played onscreen lovers in the iconic movie, the pair have always maintained that their relationship has never been romantic.
The duo later reunited to play a married couple in 2008’s Revolutionary Road, which was directed by Kate’s then-husband Sam Mendes. The experience brought the friends closer, as Leonardo surprised Kate with a friendship ring when filming wrapped up.
“ Yes, [Leo’s ring] is engraved on the inside ,” Kate previously told Flare Magazine. She declined to share what the inscription says, admitting it’s private. “I’m not going to tell you what it says,” she added.
During the same interview, Kate also revealed Leonardo gifted her with a gold necklace, which she debuted on the cover of Time Magazine. “Leo gave me this necklace,” the actress explained. “It has a little golden leaf on the bottom. Leo gave it to me.”
Despite having such a close connection, both Leonardo and Kate have denied having feelings for each other. In 2017, Kate admitted she never had a crush on Leo while filming Titanic.
“I think it was seven months of very intense work,” she said “We were both really very young, and luckily — and this is the fortunate thing — we never fancied each other. I know that’s really annoying to hear, I’m sorry, but we really never did.”
She added, “We were able to tease each other, and we still do, so it’s really amazing.”
She’s also opened up about the infamous car scene in Titanic where Rose and Jack consummate their relationship. Kate says while they were committed to the scene, it still felt off since they were never attracted to one another in the same way as their characters were.
“Doing that scene,” she explained. “It so wasn’t us. And yet, we were so locked into what all that had to be about. The Rose in me was really sort of loving the Jack in him, actually.”
Kate continued, “And even though I didn’t feel that way about Leo, it was quite nice to sort of feel that way in the scene. It was quite lovely. And then, y’know, the camera stopped rolling, and he gets up and walks off, and the scene’s done. And I remember lying there thinking, ‘What a shame that’s over.’ Because it was quite nice. It was.'”
Kate Winslet Hasn't Commented On Leonardo DiCaprios's Romantic Life
He may have never dated Kate, but Leonardo has had many girlfriends over the years. In fact, he’s developed a reputation for only dating very young women, typically in their early 20s.
Last year, the Wolf of Wall Street actor got flack after breaking up with Camila Morrone shortly after her 25th birthday. He soon began dating Gigi Hadid, 27, though there were rumors it was a publicity stunt to help improve his image, since Gigi is slightly older than the women he usually dates. However, their relationship has since fizzled out.
However, Leonardo was recently spotted getting close to 19-year-old model Eden Polani, sparking dating rumors. He instantly faced backlash, given the model’s young age.
Leonardo’s (alleged) new girlfriend may not be sitting right with Kate, considering her own daughter, Mia Threapleton, is close in age. Mia is 22 years old, putting her right in Leonardo’s preferred age category. Even if Kate wasn’t bothered by Leonardo’s dating patterns in the past, she may feel differently now that he’s rumored to be dating a teenager, who’s even younger than her daughter.
Kate Winslet May Not Mind Leo's Ways, Since She’s Married To Someone Younger

While Leonardo continues to play the field, Kate is on to her third marriage. She wed Edward Abel Smith (aka. Ned Rocknroll) in 2012. Leo played a special part in their wedding – he walked Kate down the aisle.
Kate’s current husband is slightly younger than her – he’s 45, while she’s 47. This isn’t a huge age gap, especially in comparison to Leonardo’s dating history. But since she’s with a younger guy, it could signify that Kate isn’t as bothered by Leo’s track record as others.
It remains unclear how Kate really feels about Leonardo’s reputation for dating younger women, since she’s never addressed the subject publicly. Given their close friendship, fans can expect that Kate would say something to Leonardo is she had a problem, but it’s likely that she’d do so in private.
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