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.



































Let Your Dreams Propel You Through Valleys and Over Mountains
Each one of us has a light within that radiantly burns; it never goes out. Life's challenges and inconsistencies may weigh you down, but let your dreams catapult you beyond all mental, physical, and psychological limitations -- be merciless in your pursuit of self-actualization. Use untapped potential within to fire up your internal engines; shift all gears to go, blast through all impediments. Ignore the negative environmental noise, which threatens to consume. Focus. Determine to turn all obstacles into rafts and propel yourself across life's turbulent waters. Never stop. Never give in. Never give up.
Let Your Dreams Propel You Through Valleys and Over Mountains
Aspire
Push forth with your dreams and goals no matter the setbacks. Be grateful to those who stick with you no matter what. Always find the time to say thank you to those who helped. Send them positive vibes even if they are no longer in your life. Aspire to do better at every juncture of your journey.
As a young black girl growing up in my Caribbean island home, I longed to cross the waters surrounding jagged, limestone shores. There were hardly any signs telling me I could rise above the struggle and violence of a broken home. Nevertheless, I dreamed to one day do better; I dreamed to one day go further -- I dreamed to soar.
When I mentioned my dreams to those around me, many smiled dismissive smiles. However, my mom encouraged and believed in me from her own broken place. She often said, "If anyone can do it, you can!" When inherited brokenness cost me friendships, jobs, lovers and my education, she encouraged me to keep going. She believed my dreams would take me through valleys and over mountains.
Visualize
Never lose sight of your goals and aspirations. There will be days when obstacles rise up, but have no fear -- obstacles are an important part of the process. They help you to grow, so embrace them when they appear. To me, obstacles are the universe's way of saying you are on the right track. Visualize how you want your end goal to look like as you keep surging forward.
Over the years, I figuratively crossed numerous faraway mountains and traversed countless overgrown valleys. Every step has been painstakingly minuscule, but I persisted. Over and over I shared my dream to be a published writer and artist to all who would listen. An immigrant and high school dropout with no inheritance as a buffer, I carved doors with my worn-out hands; I walked unpaved roads with my bare feet. Along the way, my determination created opportunities to meet kind-hearted people who saw my passion and helped propel me forward, eventually leading me to Mount Holyoke as a Francis Perkins Scholar.
Yes, I made many mistakes in my youth, most self-inflicted -- we sometimes do in our pursuit of betterment. However, when lessons needed learning, I evolved and kept moving at the same time.
Accept
Cultivate acceptance early. There are some situations and people you have to accept because there are no other options. Instead of fighting to hold on to the things you cannot change, accept, let go and keep flowing.
As time shuttled by I embraced humility -- I accepted those unfixable situations; I let go of unsupportive family; I gave up shallow friendships. In time, I realized, in order to give myself to others, I first had to heal my internal wounds. By accepting and taking responsibility for my shortcomings, doors opened that were previously closed. When the death of a close family member forced me to face life's unknowns and uncertainties, my faith was strengthened; when personal illness threatened my mortality, my faith was deepened. I have travelled far and wide in search of my truth -- not knowing, until now, that it was always here.
Finally, my dreams brought me back home to the place where I started. Today, even in the midst of an ongoing struggle, calm and peace still pervades no matter the crisis of the day.
Rise above
Know that all situations in your life have one thing in common: you. Take responsibility and keep making room for positive growth.
Although I had dreams that took me through difficult and dangerous mountains and valleys, I had the power and determination within me to keep going. This process is still ongoing today and will continue until I leave this earth. I am constantly reconfiguring and adjusting my dreams, even though, at the core, the goal is the same.
Nowadays, flexibility is my best friend, and I am persistent in finding ways to adapt to whatever comes my way. I found that incorporating daily self-reflection is essential to keeping my dreams alive and to manifesting my goals. Another lesson learned was the importance of embracing constructive criticism and not taking everything personally. In order to keep rising up, you must be mature enough to cast off internal slights and resentments, which tend to hold you back.
As time passes by, I continue to see the correlations between my inner and outer world. It is fascinating to see the connections; to finally understand that I am in control of my reality.
Hold fast to your dreams
In the end, the path of the pebble you threw, in the pond of your life, will ripple far and wide. Since yours is the hand that tossed it, all actions caused by that ripple will accrue to you. Do what’s necessary to uncover your truth and discover your path, but know all roads lead back to you. No matter your circumstance or situation, let your dreams take you through valleys and across mountains, but know the grass is always greener where you stand.