The teenage grief that still haunts Kate Winslet: Inside A-list actress’ doomed relationship with 27-year-old writer when she was just 15: ‘I still love him, I hope I always will’

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She became famous for playing the female lead in a hugely popular and tragic love story alongside Leonardo DiCaprio.

Even Kate Winslet’s biggest fans might not realize she experienced a heartbreaking first love of her own. Her first love tragically passed away around the same time the movie Titanic came out.

The 50-year-old actress has been married three times and had short-term relationships with actors Rufus Sewell and Louis Dowler. However, she considers her first boyfriend, Stephen Tredre, to be her true soulmate.

The man, a writer and actor famous for the BBC show Fish and his work on EastEnders, first met Kate in 1991 while working on the sci-fi series Dark Season, which also marked Kate’s first appearance on screen. It was created by Russell T Davies.

She played one of the main characters, and Stephen had a guest appearance in a single episode. Kate immediately became attracted to him, later sharing that he made her feel safe and loved, and that he was the most important person in her life after her family.

Although she says he’ll always hold a special place in her heart, their relationship has caused concern online because Kate was only 15 years old when it happened, and Stephen was 27.

She admitted to being underage when she started dating a man twelve years older. They were together for about five years, even living together, before breaking up when she turned nineteen, shortly after he received a cancer diagnosis.

Even after their split, they continued to talk regularly, especially while he was dealing with health issues – a period that also marked the beginning of her success with films like Heavenly Creatures and Sense and Sensibility.

Kate Winslet, known for her role in Eternal Sunshine of the Spotless Mind, later stated that she and Stephen Dorff spoke daily and that she would never abandon him.

Stephen died unexpectedly in December 1997 at the age of 34. Kate described his death as devastating, and shared that she was grateful they had remained close until the very end.

She’s spoken openly about the lasting impact of his death, once saying, “I still talk about Stephen like he’s my beloved, and I absolutely do still love him. I hope that feeling never fades.”

Although most people would consider a relationship between a 15-year-old and a 27-year-old problematic, Kate has consistently spoken positively about Stephen and has never suggested their relationship was wrong or inappropriate.

The mother of three has often talked about being bullied as a teenager. She’s shared how she was relentlessly teased at school, even being called names like ‘Blubber.’ She explained that she felt self-conscious about her weight, large feet, unfashionable shoes, and hair.

The experience deeply affected her self-esteem, leading her to feel inadequate and self-conscious about her body. She’s admitted to struggling with intense insecurity for years, constantly worrying that she wasn’t attractive to anyone, even well into her teenage years.

She met Stephen during a challenging period when she felt shy and insecure. He became a strong support for her, and she quickly found her life centering around him.

I remember reading an interview with her in the Los Angeles Times back in 1999, and she talked about her first love. She said he was a really supportive person during their relationship, someone she could always lean on.

He was twelve years my senior. I was fifteen when we got together, and we broke up around the time I turned nineteen. He was a really influential person who helped me become more confident and understand myself better.

Even years later, Kate still looked back on their relationship with warmth, remembering how special it was despite starting it at a young age.

In a 2006 interview with Parade, she shared that she used to be very shy and easily hurt. She was often teased and bullied, and she coped by keeping to herself and focusing on getting through it. Meeting Stephen helped her feel safe and accepted.

He was like family to me, one of the most important people in my life. We were together for four and a half years, and we talked every day. I’m sharing this for the first time, and I want to be completely open and honest about everything.

Everyone assumed my mom would absolutely lose it when she found out I was seeing someone older – twelve years older, actually! But honestly? She was totally cool with it. I mean, she didn’t freak out at all. It was so weird, but she just… accepted it. I still can’t believe it, but she really didn’t seem bothered one bit!

She remembered telling her mother about her new relationship and bracing for a negative reaction. Instead, her mother was surprisingly calm and simply asked what he was like and if she planned to introduce him to the family, as she told Rolling Stone.

By sixteen, Kate had left school and was working at a deli. She then moved into a flat in north London with her boyfriend, Stephen, who was seventeen.

Oh, Stephen… just thinking about him makes me smile! He was the most inspiring person, honestly. Every single morning, he’d fling open the curtains and just exclaim how beautiful the day was, and immediately want to go do something! He had this incredible energy, this pure joy for living. I mean, my whole world was him. Everything I did, I did thinking about him, wanting to share it with him. He just lit up my life.

I was so heartbroken when I heard about Stephen’s cancer diagnosis in 1994. It all happened so quickly, and it was especially tough because Kate was right in the middle of filming Sense and Sensibility at the time. His health just deteriorated rapidly, and it was a really difficult period for everyone.

“There was just no sense to his pain, no explanation for it,” she said. “He was so healthy, it always felt like he would live forever.”

He went through a lot – surgery to remove a tumor in his leg, followed by chemotherapy. I supported him through it all, traveling from the film set in Devon by overnight train just to be with him at the hospital.

She shared that Stephen chose to end their relationship while he was fighting cancer, a decision she saw as an act of kindness, though she’s always regretted it.

Looking back, I realize how young we both were when things ended with Stephen. It sounds strange, but after he recovered from cancer and went into remission, we just… drifted apart. Honestly, I still don’t fully understand why. It wasn’t a dramatic event, just a gradual realization that we weren’t right for each other anymore, even after everything we’d been through.

Looking back, I was really young – just nineteen. I often wonder how I could have left someone who was so sick. I genuinely believed Stephen would recover.

I’ve always been struck by how openly Kate talks about losing him. She’s said many times she never truly recovered from his unexpected passing, and truly believes their connection lasted right up until the very end. It’s incredibly moving to hear her speak so honestly about their enduring bond.

She described their connection as truly special, saying her ex-boyfriend would always hold a significant place in her heart. She emphasized that the breakup wasn’t abrupt, but a mutual decision that allowed them to remain friends.

More than ten years after Stephen’s death, she became emotional while talking about the sadness and regret she continues to experience.

You know, people often ask me about dealing with difficult past experiences. I always tell them it’s not about ‘getting over’ things, it’s about learning to live with them. Even years later, reflecting on those times can still bring up strong emotions – I find I still get a little choked up when I talk about it, honestly.

Stephen letting me go felt like an incredibly loving act, almost too much to bear. Now, looking back, I regret that he did.

I really regret not being there until the very end. It all happened so fast, and I keep replaying those final moments in my mind.

Kate chose to attend Stephen’s funeral instead of the US premiere of Titanic. She later shared that her employers had cautioned her against this decision, fearing it could harm her career.

Looking back, she told The Guardian a couple of years later that she had been quite depressed. Losing someone she’d been with for four and a half years was incredibly difficult, and she was surprised that people would even think…

People kept talking to me, offering sympathy like, ‘We know this is difficult,’ but then immediately following it up with, ‘Don’t you think Stephen would have wanted this?’

She responded sharply, saying, “Absolutely not, he would have wanted me at his funeral, and I intend to be there.” I have to admit, her reaction really worried me.

In a moving interview with Rolling Stone in 1998, she shared that she sang a song at his memorial—one he’d always enjoyed hearing her perform. She described the experience as being similar to how Elton John likely felt when he sang at Princess Diana’s funeral.

Oh my gosh, it was brutal. I was so scared of messing up, I knew if I even tried to say anything before I started singing, the tears would just come, and I wouldn’t be able to get a single note out. So I just went for it, and the instant the music stopped, I completely lost it and started choking up. It was… a lot.

In an interview on the Happy Sad Confused podcast last year, she talked about why it was important to her to go to the funeral instead of the movie premiere.

She told Josh Horowitz that even considering missing it was awful, and of course, she wouldn’t have dreamed of doing so.

I completely missed the whole Titanic craze when it came out, and I’m not sure why. Maybe it was a way of shielding me from something, or maybe it was just a nudge to focus on what’s truly important in life.

Kate reflects on the time after Titanic made her famous, saying she was going through a difficult period. She explains, ‘I was in a lot of pain and struggling to figure out who I was as a person.’

Honestly, dealing with Stephen’s passing was incredibly difficult. It’s something I’ve been open about for years, and in looking back, I even realize it influenced some of my early life choices – like, I think part of why I married Jim Threapleton so soon after was because I was still processing the grief.

While filming Hideous Kinky, she met the assistant director and they had a daughter, Mia, in 2000. However, they separated after only six months.

She later admitted their marriage was deeply troubled. Recalling her decision to leave, she explained she was scared, but understood she had no choice. She felt a sense of urgency, as if time was running out.

Kate shared that when Stephen unexpectedly passed away during the filming of Hideous Kinky, it brought her closer to Jim, who was there to support her while they worked.

She admitted the film was difficult to finish, but focusing on doing it for Stephen helped. Meeting Jim and his support also made the experience much easier.

Looking back on her fast-moving romance with Jim in 2006, she confessed that she’d initially thought he was what she needed. She was still heartbroken over the loss of Stephen and overwhelmed by the massive success of ‘Titanic,’ and Jim seemed like a normal, grounding presence in her life.

After her divorce, Kate started seeing Sam Mendes, who would become her second husband. However, she was unfairly criticized, with some people claiming she was simply replacing her ex-husband with someone more successful.

Although she admitted the strong negative reaction was deeply upsetting, she emphasized that it didn’t compare to the pain of losing her son, Stephen.

Kate recently shared that she felt many people in the UK struggle with grief. She explained that working on her new film felt like a way to process the loss of her mother, Sally, who sadly died from ovarian cancer in 2017.

I was deeply moved by Kate’s first film as a director, ‘Goodbye June’. It’s a beautiful story about four siblings coming together to be there for their mom as she faces health challenges, and honestly, it really resonated with me on a personal level. It brought up a lot of feelings, and I think it will for anyone who sees it.

Oh my gosh, she just broke my heart talking about her mom! She said it honestly feels like yesterday since she passed, almost ten years later! And it was so raw hearing her talk about how hard it was to play Julia, June’s daughter in the movie, because it kept bringing up her own grief. You could just feel how personal it was for her, it was so incredibly moving!

Kate recently shared on the Happy Place podcast that working on a fictional film brought back painful memories of losing her own mother. While she didn’t find the process particularly healing, she described vividly reliving those feelings and, surprisingly, trying to distance herself from the emotions in a quirky way.

During the more personal scenes, like those with Helen Mirren and Tim Spall, I’d quietly sit in the room and hide behind Max, our focus puller. I’d watch the monitor with him and often found myself quietly crying into his back.

She added that, in this country, we generally struggle to discuss loss and cope with grief.

It actually sparked a lot of important conversations, and people – not just the actors, but crew members too – really appreciated being able to have them.

Kate’s relationship with Stephen influenced how she viewed age-gap romances, a point highlighted by an uncomfortable interview with The Guardian in 2008. The interview focused on her role as Hanna Schmitz in the film The Reader, a performance that ultimately earned her an Academy Award.

As someone who often delves into the complexities of characters, I was recently asked a really challenging question. People wanted to know if I could understand, or even sympathize with, a role I was considering – a woman in her mid-thirties who, in her past, served as a guard at a concentration camp, and who is now involved in a very inappropriate relationship with a teenage boy. It’s a tough one, honestly, because it forces you to confront some incredibly difficult moral questions and really explore the depths of human behavior.

In the UK, the legal age for sexual activity is 16, no matter a person’s gender, sex, or sexual orientation. This means sexual activity with anyone under 16 is illegal, even if they consent.

When journalist Kira Cochrane pointed out that the relationship in The Reader might be considered ‘paedophilia’ by today’s standards, Kate Winslet reportedly reacted strongly, telling Cochrane to ‘be careful with that word’.

When the interviewer tried to make sure she understood, asking ‘Do you know what I mean?’, the actress replied, ‘Actually, no, I don’t understand when you use that particular word.’

When Kira questioned if it was appropriate considering he was only 15, Kate firmly repeated her stance. She emphasized, “No, I don’t think so, not to that degree. To be honest, I believe using that term is very dangerous, especially when talking about children who haven’t gone through puberty.”

It’s important to remember the age dynamics in the story. The boy character turns sixteen, which is the legal age for marriage, and Hanna believes he’s seventeen. Interestingly, the actor who plays him, David Kross, was actually eighteen during filming – a legal adult himself.

To be honest, both as myself and playing the character, I always saw the relationship as unusual – largely because of the significant age difference. Ultimately, I viewed it as a love story, but definitely one that wasn’t conventional.

The interview remained cold, and Kate then brought up her relationship with Stephen, stating that age had never been a concern for her.

She unexpectedly shared that a significant early love was thirteen years older than her, and they were together for five years until he passed away. Considering her grandparents had a nineteen-year age difference, she’s never really seen age gaps as a big deal.

She reiterated her frustration with discussions about age differences in relationships in 2015, following her role in another movie featuring a significant age gap between the romantic leads.

In the comedy-drama The Dressmaker, Kate Winslet starred as a dressmaker who develops a romance with a man much younger than herself, played by Liam Hemsworth – he was 14 years her junior.

You know, when I spoke with the actor about taking on this role, he was surprisingly candid. He confessed he’d actually been quite anxious about it! He felt, and I quote, that he might be a little too young to really nail the character, which I found fascinating. It’s always interesting when talented people have those self-doubts, isn’t it?

Kate said the age gap with Liam Hemsworth wasn’t something she thought much about. She shared that her 15-year-old daughter recently pointed out that Liam is actually closer in age to her daughter than he is to Kate herself, according to a BBC interview.

I was just impressed! I hadn’t given age any thought, and I don’t really let things like that worry me.

Following her divorce from Sam in 2010 – after seven years together and the birth of their 21-year-old son, Joe – Kate found love again with Edward Abel Smith, who is Richard Branson’s nephew.

Kate and her family were vacationing on Necker Island in the British Virgin Islands in 2011 when a lightning strike caused a fire in their house. That’s where she met the man who would become her partner.

The actress realized she’d found her soulmate when Edward, who was then going by Ned Rocknroll, helped her and her family get away. They married the next year and had a son, Bear Blaze, in 2013.

She once told The Telegraph that she knew immediately this person was who she was meant to spend her life with, and she feels the same way today.

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2025-12-21 19:23