Renée Zellweger’s blink-and-you-missed-it marriage 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 on, let’s look back at what really became of Renée ‘n’ Kenny…
How it Began
It was at NBC’s Concert of Hope (a tsunami aid telethon) in January 2005 that Zellweger, now 55, and Chesney, now 56, first met — but this was no chance encounter. The Bridget Jones actress had already planned to pass a note to the country star after admiring him from afar. Chesney, meanwhile, had cited her as one of his top celebrity crushes in a 2002 interview with The Tennessean, saying “Here’s a country girl who’s still down to earth. You never see her coming, then — wham! — there she is. And that makes her really, really sexy. Plus she seems like the kind of girl who could fit in and be at home anywhere.” His 1999 song, “You Had Me From Hello,” was also rumored to have been inspired by seeing the actress utter a nearly-identical line in 1996’s Jerry Maguire.
The story, as told by entertainment expert and former People magazine Editor-in-Chief Jess Cagle, goes that after the telethon, where Chesney was performing and Zellweger was answering phones, he approached her and said “I hear you are trying to pass me a note — don’t let the principal find out!” and the pair promptly started getting to know each other.
“They had each other from hello,” said Cagle at the time. “At that point, they exchanged numbers and emails and started this sort of long-distance relationship that became a real romantic thing.”
The first public hint of a romance between the pair came in April, when Zellweger unexpectedly appeared on stage with Chesney at his show in Jacksonville, Florida, presenting him with a margarita and kissing him on the cheek.
How Long it Lasted
This is the part that got everybody talking.
After less than four months of dating, the couple got married in May 2005 in an intimate ceremony at Chesney’s private estate on St.John in the U.S Virgin Islands. Zellweger wore a Carolina Herrera gown and was walked down the aisle by her father, with 35 close friends and family members in attendance.
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 went public, there was fierce speculation about what “fraud” might mean, even leading to intrusive speculation about Chesney’s sexuality (which he later addressed head-on).
Zellweger released a statement to clear things up, saying she wanted to “clarify that the term ‘fraud’ as listed in the documentation is simply legal language and not a reflection of Kenny’s character.” She added: “I would personally be very grateful for your support in refraining from drawing derogatory, hurtful, sensationalized or untrue conclusions and greatly appreciate your understanding that we hope to experience this transition as privately as possible.”
Sometimes relationships don’t work out — just ask any celebrity couple who has had their marriage annulled. “He said all the right things and I and the families were a good, good fit. And he seemed to grow up similarly to me. It was almost like an arranged marriage, I felt like, except we chose […]
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 everyone can respect the privacy that I know Renée has already asked for.”
But still the gossip rumbled on, forcing the couple to issue yet another statement — this one, together, and via their reps. They said: “The miscommunication of the objective of their marriage at the start is the only reason for this annulment. Renée and Kenny value and respect each other and are saddened that their different objectives prevent the success of this marriage.”
Both stars mostly laid low in the immediate aftermath but in November 2005, two months after the annulment, Chesney was complimentary towards his ex in an interview on The View. “She and I fell in love like a couple of schoolkids,” he said. “I’m glad to know that can happen, that that exists and we still really care about each other. It would’ve been a bad thing if I hadn’t met her. She’s wonderful. I don’t want to sit here and go: ‘Poor me.’ I am totally blessed, and I’m grateful for it.”
What They Say Now
Now that more time has passed since the brief, some might say doomed marriage, both parties have felt more able to speak about what really went down.
Sometimes America’s sweethearts go sour. From Morgan Wallen to The Chicks, the biggest names in country music 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. While performing across the […]
“I think people need to live their lives the way they want to, but I’m pretty confident in the fact that I love girls,” said Chesney in a 2009 Playboy interview. “I’ve got a long line of girls who could testify that I am not gay. In order for us to get an annulment, the legal papers could claim either physical abuse, which wasn’t true, or three or four other things that also weren’t true. The best thing we could put in there was fraud. So I said, ‘All right, do it. Whatever’.”
In a 2010 interview, he gave a few more details — and it sounded like he simply wasn’t ready for marriage. “I look at my life as a box,” he said. “So everything that I put in — learn how 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 wonderful house… And you protect everything and all the relationships and all the people that helped you build that house. “It was out of the box. [Renée’s] a sweet soul, no doubt about it, but I just wasn’t ready…. This is the first time I’ve actually talked about it, but that’s what happened.”
In another Playboy interview, in 2015, Chesney was even more reflective about the turn of events, and the impact on his life. “Nothing positive at all in my life came from it, I can tell you that,” he said. “I didn’t have any clue as to what true marriage meant. I was so used to committing to one thing — music — and then I had to totally commit to a second thing, marriage. I didn’t know how. It was a scary moment for me. I had never really had any kind of attention from the paparazzi. It went from zero to the complete other end of the spectrum. I’d go to a concert and there would be helicopters circling, trying to get a picture of me and her together. I thought it would be like that all the time. I just totally panicked. I did the only thing I knew to do: I ran. I pushed her away, in every way possible—to the point where I just didn’t want to be married to her anymore. It’s that simple. I still struggle with it. Was it the right thing to do or not? I still think about her every day. Every day I wonder if she’s okay. I mean, you don’t just fall out of love with somebody.”
More recently, in a 2023 interview with Billboard, Chesney talked about how his experience with Zellweger had made him conduct his life more privately. “One of the reasons I’m so private is when my life started to change and people started caring at a different level, the only thing I could keep to myself was the intimate details of my life,” he said. “What is interesting is we were playing stadiums already, and after that … I didn’t have social anxiety before that, 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 greatest 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 pair called it quits following the […]
Zellweger has also spoken about the tumultuous period of her life, and said in a 2016 interview with The Advocate that the speculation about Chesney’s sexuality really upset her. “It made me sad that somehow people were using that as a way to be cruel and calling someone gay as a pejorative, which has fateful consequences,” she said. “Of course, there’s the bigger-picture problem of why anyone had to make up a story at all. I’m an old-fashioned gal who doesn’t feel it’s appropriate to hang out your laundry on the lawn. I feel you devalue yourself as a human being when you share very personal things with a bajillion strangers who are making fun of you. I just don’t see that there’s any dignity in that.”
Zellweger added that she often forgot the marriage had ever happened, saying “It’s a pretty big thing to forget, isn’t it?”
Key Relationship Takeaways
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 afar — but forgot to actually figure out if they were compatible. Both in their mid thirties at the time, getting married probably felt like the obvious thing to do.
An unexpected match! Ant Anstead continued to make headlines after his split from Christina Haack by sparking an A-list romance with Renée Zellweger. The Wheeler Dealers star was previously married to Haack for nearly two years before the pair announced their separation via Instagram in September 2020. Nine months later, Us Weekly confirmed that the […]
Two decades later, both are in long-term relationships — just not with each other. Chesney has been dating model and dancer Mary Nolan since 2012 — and their relationship is extremely private — while Zellweger has been with British TV star and motor specialist Ant Anstead since 2021. Interestingly, though, neither party has ever married again; did those disastrous few months put them both off for life?
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