From declarations of love to laughter on the red carpet, we've rounded up our favorite moments between the legendary Leonardo DiCaprio and Kate Winslet that have kept our hearts aflutter for over two decades.
The now 50-year-old Leo and 49-year-old Kate have had their share of memorable moments. And they're still culturally relevant. The 2023 film Anyone But You had Sydney Sweeney and Glen Powell recreate the Jack and Rose "leaning over the deck of the Titanic" scene we'll never forget.
Their First Kiss on the set of the Titanic
commons.wikimedia.orgMeeting on the set of Titanic in 1997, DiCaprio and Winslet instantly clicked amidst the gruelling seven-month shoot. Their chemistry was palpable, but both actors have insisted that their bond was purely platonic. Winslet once shared that while her friends were swooning over DiCaprio, to her, he was just “silly old Leo.” This early connection started a friendship that would endure the test of time and Hollywood’s pressures.
Oscar Buzz and Romance Buzz

Photo By Ron Wolfson/Getty Images
Their friendship has only blossomed over the years, punctuated by countless public appearances that left fans buzzing. Take the 1998 Golden Globes, for instance—Leo and Kate’s camaraderie was on full display as they cheered each other on, despite the endless swirl of romantic rumors. This pattern of mutual support and affectionate displays has persisted, proving that true friendship not only survives but thrives under the bright lights of Hollywood’s spotlight.
Reuniting On The Silver Screen

Kate Winslet and Leonardo DiCaprio on the set of Revolutionary Road
In 2008, DiCaprio and Winslet reunited on screen for Revolutionary Road, a film about a disintegrating marriage. Despite the intense and somewhat uncomfortable scenes, especially with Winslet’s then-husband Sam Mendes directing, their chemistry was as electric as ever. Winslet later reflected on their effortless ability to fall back into sync, likening it to muscle memory. This reunion showcased their incredible acting skills and highlighted the depth of their enduring friendship.
She Thanked Leo (Before Her Husband)!
At the 2009 Golden Globe Awards, Cameron Diaz and Mark Wahlberg presented the award for Best Actress in a Motion Picture Drama to Kate Winslet for her stunning performance in Revolutionary Road. Winslet, overwhelmed with emotion, took the stage and apologized to the other nominees before expressing her disbelief at winning a second award that night.
In her heartfelt speech, she thanked the Hollywood Foreign Press, her longtime agents, writer Richard Yates, the film’s cast and crew, the producers, the hair and makeup department, her dialect coach, and, notably, her co-star Leonardo DiCaprio before her husband and the film's director, Sam Mendes. Among the nominees were heavyweights like Anne Hathaway, Angelina Jolie, Meryl Streep, and Kristin Scott Thomas.
Winslet made sure to acknowledge her longtime friend and Revolutionary Road co-star, saying, "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."
Leo Walked Kate Down The Aisle

Photo by Alexandra Wyman/WireImage
In 2012, during a secret ceremony in New York, it was rumored that Leonardo DiCaprio gave Kate Winslet away at her wedding to Ned Rocknroll (born Abel Smith). This touching gesture demonstrated the depth of their bond, with DiCaprio standing by his friend’s side during one of the most significant moments of her life. This act of friendship showcased the unwavering support and love they have for each other, further cementing their status as one of Hollywood’s most beloved duos.
And The Oscar Goes To...
HOLLYWOOD, CA - FEBRUARY 28: Actor Leonardo DiCaprio (L) and Kate Winslet attend the 88th Annual Academy Awards at Dolby Theatre on February 28, 2016 in Hollywood, California. Photo by Christopher Polk/Getty ImagesWho can forget the 2016 Oscars when DiCaprio, finally nominated for his role in The Revenant, surprised Winslet on the red carpet? The reunion sparked joy and nostalgia for fans, reminding everyone of their timeless bond that began with Titanic.
During DiCaprio’s acceptance speech, Winslet couldn’t hold back her tears. As he spoke about the importance of protecting our planet, the camera caught Winslet’s emotional reaction, proving just how much his success meant
They Didn't See Each Other For 3 Years!

HOLLYWOOD, CA - FEBRUARY 28: Actors Leonardo DiCaprio (R) and Kate Winslet attend the 88th Annual Academy Awards at Hollywood & Highland Center on February 28, 2016 in Hollywood, California.
Photo by Dan MacMedan/WireImage
The COVID-19 pandemic posed a significant challenge to their friendship, as travel restrictions kept them apart. Winslet described their emotional reunion after nearly three years as tear-filled and overwhelming, emphasizing how much they missed each other. “I couldn’t stop crying,” Winslet confessed, illustrating the profound connection they share. This reunion underscored the strength of their bond, one that thrives even in challenging times.
Their friendship was once again in the spotlight during the release of Titanic's 4K Ultra HD edition, where Winslet reminisced about their early days on set. She described young DiCaprio as a magnetic presence, full of energy and freedom, qualities that made working with him a delightful experience. Winslet’s reflections remind us of the joyful and enduring nature of their bond.
Nearly 30 Years of Friendship

BEVERLY HILLS, CA - JANUARY 11: Actors Kate Winslet (L) and Leonardo DiCaprio arrive at the 66th Annual Golden Globe Awards held at the Beverly Hilton Hotel on January 11, 2009 in Beverly Hills, California.
Photo by Kevork Djansezian/Getty Images
Leonardo DiCaprio and Kate Winslet’s friendship is a testament to the enduring power of genuine human connection amidst the glitz and glamour of Hollywood. Their story, filled with shared memories, mutual respect, and unwavering support, continues to inspire fans worldwide. In an industry where relationships can often be fleeting, their bond stands out as a heartwarming example of true friendship.
From their early days on the Titanic set to walking each other down the aisle and supporting each other’s career milestones, DiCaprio and Winslet's friendship reminds us that childhood friends never get old. As Winslet once said, “We’re bonded for life,” a sentiment that perfectly captures the deep and abiding connection they share.






































The 3 Main Signs You’re a Hopeless Romantic (and Why That’s Not a Bad Thing)
A hopeless romantic cant help but dream of their perfect partner, but there's a negative association with the term that we should change.
My name is Ricky and I’m a recovering hopeless romantic. I’ve been battered and bruised by unmet expectations, the slow crumbling of unrealistic fantasies, and the gradual jadedness of looking for an idealized version of love. In my younger years, I had big ideas and even bigger visions for what true love meant. A love free from pain, a love that offered salvation, a way to rise above the mundane, the struggle and strife of daily life, with someone by your side.
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I’ve experienced the poetically tragic and the ineffably beautiful. And, I’m here to reassure you. Because amidst the hopeless romance, there is hope. Hope for a more mature, balanced approach to love. One which catapults you to deeper levels of fulfillment, doesn’t avoid the tough stuff, and allows you to, paradoxically, get closer to the type of love you may have always longed for.
What Does It Mean to Be a Hopeless Romantic?
It’s likely you already know what it means to be a hopeless romantic. What image intuitively surfaces? The hopeless romantic is an archetype in its own right, playing out over and over in stories, music, film, and poetry. The phrase dates back to around the early 1920s, appearing in a short story collection, to describe the mixture of “ passionate (romantic) yet ineffectual (hopeless) love.”
Dictionary.com’s definition of a hopeless romantic is:
A hopeless romantic has high ideas for love and will do all they can to pursue them. Of course, characters we read on pages or see on screen often reflect emotional or psychological processes within; there is truth in fiction. Many of us have the inner hopeless romantic, a yearning to find “the one,” a desire to pursue love at all costs, to place it above all else.
Signs You’re a Hopeless Romantic
It’s likely, if you’re reading this article, you have experienced enough red flags in romance to know your patterns need closer inspection. Above all else, the biggest sign of hopeless romantics is that romantic love, or more accurately romantic drama, consistently takes up a lot of space. Either in being distracted by a new love, engaging in toxic relationships, recovering from conflict, or becoming codependent. Other signs include:
1. You Use Romance Is An Escape
Hopeless romance is immature, to a certain extent. The desire for fairytale romance is naive. Relationships take work. Beyond the honeymoon period of falling in love, a relationship will challenge you to grow and mature. You’ll need to navigate your own shadow, trauma, and defense mechanisms. You’ll need to work on communicating whilst triggered, or overcoming emotional fallouts.
All of this is anything but an escape. In facing someone else, relationships encourage you to face yourself. Hopeless romantics, however, tend to view romance as an escape. The desire for this type of love is a way to bypass difficult feelings, obligations, or responsibilities.
2. You Experience Many Passionate But Short-Term Relationships
Because hopeless romance is founded in an idealized version of love, many people find that, when the going gets tough and the fantasy starts to dissolve, they leave the relationship to pursue someone else. If love doesn’t match expectations, it’s always the relationship’s fault or the other person’s fault. Without self-awareness, this perpetuates the cycle of chasing, falling, and becoming disillusioned. As a result, many hopeless romantics get stuck in a simultaneous state of yearning and cynicism.
3. You Prioritize Romance Above All Else
There’s a difference between prioritizing meaningful relationships and family, from a place of service or love, and the hopeless romantic’s approach to prioritizing. A hopeless romantic will place the pursuit of romance above all else, often leading to codependent relationships that are so intense, and lacking in personal boundaries, other areas of life become neglected. They stop seeing friends or pursuing solo hobbies or interests.
Despite being unhealthy, hopeless romantics get trapped, because their idea of love means giving it everything, being passionate, and making sacrifices. There’s a seed of truth in all of this — love does require giving, passion, and sacrifice. But when it comes from an imbalanced sense of martyrdom, or a need, it becomes unhealthy.
Is Being a Hopeless Romantic Unhealthy?
Modern portrayals of love emphasize this mixture of passion and ineffectiveness. Forbidden or impossible love makes for a dramatic story. What would The Notebook be without arguments or barriers to love between Noah (Ryan Gosling) and Allie (Rachel MacAdams)? Or Jack (Leonardo DiCaprio) and Rose (Kate Winslet) in the Titanic? Or, stretching further back to the greatest hopeless romance of all, Shakespeare’s Romeo and Juliet?
Of course, normal isn’t healthy by default. Hopeless romance often comes from a place of innocence. How can you argue against believing in love? Or wanting to find someone to share life with? The question then is, how does hopeless romance surface, and in what ways is it unhealthy, limiting, or holding you back?
I explored all of this in detail through my “recovery” from hopeless romance. Like most hopeless romantics, it got to the point where I knew something had to change because I was experiencing regular setbacks and heartbreak. I sensed I was stuck in various cycles of high expectations and disappointment, and intuitively felt I was placing too much value on my partner.
Impaired Spirituality, or More Satisfaction?
In Facing Love Addiction, codependency expert Pia Mellody explains one of the biggest pitfalls of hopeless romance — making your partner your higher power. By replacing your sense of spirituality or transcendence in a relationship, it’s possible to impair its healthy expression. This leads people to “try harder and harder to manipulate the other person to live up to the mental image they have created — that is, someone who will care for and love them the way they long to be cared for and loved.”
However, it’s not all bad. One study in the Journal of Social and Personal Relationships discovered that people in long-term relationships who had romantic beliefs reported greater satisfaction. According to the study, “romantic beliefs do not appear to foster false or unobtainable expectations for romantic relationships, and the concerns regarding the endorsement of these beliefs may be misplaced.”
The Hope Isn’t Lost in Love
I promised you there would be reassurance, and here it is — being a hopeless romantic isn’t a bad thing. I know from experience that there’s a temptation to judge yourself when spotting these patterns. How could you ignore the warning signs, and get stuck again and again? Part of the process of growth is to take what works, let go of what doesn’t, and build towards a healthier model of love.
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If you’re single, consider how you can reclaim the power you’ve given to the pursuit of finding “the one”. Know that true fulfillment comes from within. That being said, a deep, intimate relationship requires a mixture of self-fulfillment and giving. Don’t discard or suppress the inner romantic. Give a voice to that part of you, but don’t make it the leader of your inner kingdom.
The eternal optimism of hopeless romantics is something to admire. You don’t have to become cynical or give up, although that is often part of the recovery process. After exploring this within myself, and vowing never to be in a relationship again, I eventually entered a relationship that asked me to cultivate true love.
It’s not always pretty. But we are growing together, because it’s confronting and grounding, and doesn't allow us to escape. Best of all, there’s still space for passion, and romance, along with a wider spectrum of experience. The more these barriers and unrealistic expectations dissolve, the more vibrant the essence of romance blossoms. Not as a naive fantasy, but something we allow ourselves to indulge in, an expression that has found its rightful place.
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