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Renee Zellweger‘s blink-and-you-missed-it wedding to country singer Kenny Chesney was so short-lived that even the actress herself sometimes forgets it ever happened – but at the time it was one of the biggest celebrity dramas around. Twenty years later, let’s take a look at what really became of Renée ‘n’ Kenny…
How it started
It was during NBC’s Concert of Hope (a tsunami relief telethon) in January 2005 that Zellweger, now 55, and Chesney, now 56, first met — but this was no chance meeting. The Bridget Jones the actress was already planning to pass a note to the country star after admiring him from a distance. Chesney, meanwhile, had listed her as one of his biggest celebrity crushes in a 2002 interview. The Tennesseanand said, ‘Here’s a country girl who’s still sober. You’ll never see her coming – boom! – there she is. And that really makes her very sexy. Plus, she seems like the kind of girl who could fit in anywhere and feel at home.” It was also rumored that his 1999 song, “You Had Me From Hello,” was inspired by seeing the actress deliver a nearly identical line in the 1996 song. Jerry Maguire.
The story, as told by entertainment expert and former People editor-in-chief of the magazine Jess Caglegoes that after the telethon, where Chesney performed and Zellweger answered the phone, he approached her and said, “I hear you’re trying to pass me a note—don’t let the director find out!” and the pair immediately began to get to know each other.
“They said hello to each other,” Cagle said at the time. “At that point they exchanged numbers and emails and started a kind of long-distance relationship that became really romantic.”
The first public hint of a romance between the couple came in April, when Zellweger unexpectedly appeared on stage with Chesney at his show in Jacksonville, Florida, handed him a margarita and kissed him on the cheek.
How long it took
This is the part everyone was talking about.
After less than four months of dating, the couple married in May 2005 in an intimate ceremony at Chesney’s private estate on St. John in the US Virgin Islands. Zellweger wore a Carolina Herrera dress and was walked down the aisle by her father, in the presence of 35 close friends and family members.
It all seemed dreamy, but after less than four months, Zellweger filed for an annulment, citing “fraud” as the reason for the split.
How it ended
When news of the shocking breakup became public, there was intense speculation about what “fraud” might mean, even leading to invasive speculation about Chesney’s sexuality (which he later addressed head-on).
Zellweger released a statement to clarify matters, saying she wanted to “make it clear that the term ‘fraud’ as stated in the documentation is simply legal language and is not a reflection of Kenny’s character.” She added: “I would personally be very grateful for your support in refraining from drawing derogatory, hurtful, sensational or untrue conclusions and I greatly appreciate your understanding that we hope to experience this transition as privately as possible.”
Sometimes relationships don’t work out – just ask a famous couple who had their marriage annulled. “He said the right things and I and the families fit together well. And he seemed to grow up the same way I did. It almost felt like an arranged marriage, only we chose it […]
What they said about each other
Chesney responded to Zellweger’s statement with his own words. “This is an incredibly sad time,” he said. “I just hope that everyone can respect the privacy that I know Renée has already requested.”
But the gossip still continued, forcing the couple to make another statement – this one, together and through their representatives. They said: “The miscommunication about the purpose of their marriage at the beginning is the sole reason for this annulment. Renée and Kenny value and respect each other and are saddened that their different goals are hindering the success of this marriage.”
Both stars mostly kept a low profile in the immediate aftermath, but in November 2005, two months after the annulment, Chesney was complimentary of his ex in an interview on The view. “She and I fell in love like a couple of college kids,” he said. “I’m happy to know that that can happen, that that exists and that we still really care about each other. It would have been a bad thing if I hadn’t met her. She’s great. I don’t want to sit here and say, ‘Poor me.’ I am completely blessed, and I am grateful for it.”
What they say now
As more time has passed since the brief, some might say doomed marriage, both parties felt better able to talk about what really happened.
Sometimes America’s sweethearts turn sour. From Morgan Wallen to The Chicks, country music’s biggest names have been at the center of some major controversies. Natalie Maines, Martie Maguire and Emily Strayer found themselves in hot water in the early 2000s after sharing their personal politics on a public stage. During the performance about the […]
“I think people should live their lives the way they want to, but I’m confident that I like girls,” Chesney said in 2009. Playboy interview. ‘I have a long line girls who could testify that I am not gay. To get an annulment, the legal documents could claim physical abuse, which wasn’t true, or three or four other things that weren’t true either. The best we could put into it was fraud. So I said, ‘Okay, do it. Whatever’.”
In a 2010 interview, he gave a few more details — and it sounded like he just wasn’t ready for marriage. “I see my life as a box,” he said. “So everything I put in – learn to play guitar, put that in the box. The friends I made. I put that in the box and my career grew. That box grew into this beautiful house… And you protect everything and all the relationships and all the people who helped you build that house. “It came out of the box. [Renée’s] a sweet soul, no doubt about that, but I just wasn’t ready for it…. This is the first time I’m actually talking about it, but that’s how it happened.”
In another Playboy During a 2015 interview, Chesney reflected even more on the turn of events and its impact on his life. “Nothing positive has come out of it at all in my life, I can tell you that,” he said. ‘I had no idea what a real marriage meant. I was so used to being committed to one thing – music – and then I had to commit completely to a second thing: marriage. I didn’t know how. It was a scary moment for me. I’d never really had any attention from the paparazzi. It went from zero to the whole other end of the spectrum. I went to a concert and there were helicopters circling around trying to take a picture of me and her together. I thought it would be like this all the time. I just completely panicked. I did the only thing I knew I had to do: run. I pushed her away in every way possible – to the point where I just didn’t want to marry her anymore. It’s that simple. I still have trouble with it. Was this the right thing to do or not? I still think about her every day. Every day I wonder if she is okay. I mean, you don’t just fall in love with someone.’
More recently, in a 2023 interview with BillboardChesney talked about how his experience with Zellweger had made him live his life more privately. “One of the reasons I’m so private is that when my life started to change and people started caring for me on a different level, the only things I could keep to myself were the intimate details of my life,” he said. “What’s interesting is that we were already playing in stadiums, and after that… before that I didn’t have social anxiety, then you add our success and then you add that to your life and you have a little bit of social anxiety. And now, dealing with the way the world is today and how social everything is, and how information is transferred – yeah, you’d have to be crazy to want to be a celebrity today.”
Some of country music’s best songs are about heartbreak, and the relationships that inspired them can be just as dramatic. Shania Twain learned that firsthand when her husband of 14 years, Robert “Mutt” Lange, had an affair with her former personal assistant, Marie-Anne Thiébaud, in May 2008. The couple called it quits after the […]
Zellweger has also spoken about the tumultuous period of her life, saying in a 2016 interview with The lawyer that the speculation about Chesney’s sexuality really upset her. “It made me sad that people somehow used that as a way to be cruel and call someone gay pejoratively, which has disastrous consequences,” she said. “Of course there’s the bigger issue: why anyone had to make up a story in the first place. I’m an old-fashioned gal who doesn’t think it’s appropriate to hang your laundry out on the lawn. I feel like you devalue yourself as a human being when you share very personal things with a billion strangers who make fun of you. I just don’t see that there’s any dignity in that.”
Zellweger added that she often forgot the marriage ever happened, saying, “It’s a pretty big thing to forget, isn’t it?”
Key takeaways for relationships
Looking back, it seems like these two just got carried away with the romance and passion of falling in love after admiring each other from a distance – but forgot to find out if they were compatible. Both were in their mid-thirties at the time and marriage probably seemed like an obvious thing to do.
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Twenty years later, both are in a long-term relationship – just not with each other. Chesney is in a relationship with a model and dancer Mary Nolan since 2012 – and their relationship is extremely private – as Zellweger works with the British TV star and car specialist Ant Anstead since 2021. Interestingly, neither party has ever remarried; Did those disastrous months ban them both for life?