Renee Zellweger's relationship history: As the actress quietly 'plans wedding' to Ant Anstead - a look back at her past whirlwind romances with Jim Carrey, Kenny Chesney and Bradley Cooper

July 19, 2023
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While Renee Zellweger's beloved character, Bridget Jones, might be unlucky in love, but she is reportedly happier than ever after accepting Ant Anstead's proposal.

Following just over two years of dating, the Oscar winner, 54, is planning an 'incredibly private' wedding with the 44-year-old British TV presenter, according to The Sun.

While an insider told the publication that the couple are not planning a 'big public announcement,' she has begun 'telling her inner circle about organizing their nuptials.'

'Everything will be very low-key,' the source added. 'Her relationship with Ant is super strong and they're madly in love, and they can't wait to get hitched.'

Amid the exciting news, DailyMail.com took a look back at her number of high-profile romances, from Jim Carrey and Bradley Cooper to her four-month marriage to Kenny Chesney.

Famous exes: While Renee Zellweger 's beloved character, Bridget Jones, might be unlucky in love, she is reportedly planning to walk down the aisle with her boyfriend Ant Anstead

Jim Carrey (1999-2000)

Sparks flew between the actress and her costar, Jim Carrey, on the set of their 1999 movie Me, Myself and Irene.

After wrapping filming on their comedy, the pair began dating and attended the 2000 Golden Globes together.

Despite the brief length of their relationship, he described her as the 'great love of' his life in his 2020 semi-fictional book, Memoirs and Misinformation.

20 years after calling it quits on their whirlwind romance, he also referred to his ex as someone 'very special' to him.

'I think she's lovely,' he said on The Howard Stern Show.

While their film's director, Bobby Farrelly that Carrey 'flipped for her immediately' on, she was hesitant to mix business and pleasure.

At the time, she told CNN: 'I liked him, a lot, but you're not going (to the set) for the love connection...When the picture wrapped, we'd spoken a couple of times on the phone and then all those rumours came out that I was dating him. I was so mad.'

After denying the rumors, she joked about getting home and thinking: 'God, I do miss him.'

Ahead of their breakup, Zellweger proudly called their relationship 'a very unexpected, wonderful thing.'

In the same interview with Entertainment Weekly, he gushed: 'She's a very connected person. She thinks having a good time is renting a U-Haul and taking furniture to Texas. She's real in that way and I absolutely love it.'

Despite speculation they were engaged during their one-year romance, she denied the claims to Cosmopolitan in 2003.

'I'd only been dating him for three months. As if I would consider marriage after only three months!' she mused.

So in love: Sparks flew between the actress and her costar, Jim Carrey, on the set of their 1999 movie Me, Myself and Irene (seen in 2000)

Smitten with each other: Ahead of their breakup, Zellweger proudly called their relationship 'a very unexpected, wonderful thing' (seen in 2000)

Jack White (2003-2004)

After playing the field for a few years, the native Texan found love on set again, this time while shooting the 2003 civil war epic Cold Mountain, for which she won the Academy Award for Best Supporting Actress.

Her fateful meeting with rocker Jack White, who is six years her junior, led to them dating for a year and a half.

White had been commissioned to write music for the movie, and had a small role playing her husband.

Although the couple rarely spoke about their relationship, they made a public appearance together at the 2004 Oscars.

During their relationship, he infamously got into a physical altercation with his bandmate, Jason Stollsteimer, which he pled guilty to, according to Rolling Stone.

He was fined $500 and sentenced to court-appointed anger management classes for his assault and battery charge.

Upon announcing their breakup, the actress' spokesman said in a statement: 'They remain good friends. There's no scandal and no new relationships.'

Love on set again! After playing the field for a few years, the native Texan found love on set again, this time while shooting the 2003 civil war epic Cold Mountain, for which she won the Academy Award for Best Supporting Actress; seen in 2004

Younger man: Her fateful meeting with rocker Jack White, who is six years her junior, led to them dating for a year and a half

Kenny Chesney (2005)

Zellweger and country music singer Kenny Chesney experienced a meet-cute worthy of a rom-com, after both attending NBC's Concert of Hope tsunami aid telethon in January, 2005.

After reportedly hoping to meet him at the event, and pass him a flirty note, a source told People that once the 'broadcast wrapped' he approached Zellweger and said: 'I hear you are trying to pass me a note — don't let the principal find out.'

Two years prior, he listed her as one of the three sexiest people on earth in 2002 during a chat with The Tennesseean, alongside, Charlize Theron and Janet Jackson.

'Here's a country girl who's still down to earth,' the singer said. 'That makes her really, really sexy. Plus she seems like the kind of girl who could fit in and be at home anywhere.'

Months after discovering their mutual crush on each other, Zellweger confirmed they were a couple by bringing him margarita and sharing a kiss with him on stage at one of his concerts.

After three months of dating, they wed on the island of St. John in the U.S. Virgin Islands.

To the world's shock, just four months later, in September 2005, she filed to annul their marriage, citing 'fraud' as the reason.

Neither has provided any further information on their split, but she did said that it made her 'said' to see widespread speculation that their marriage failed because Chesney was 'gay.'

'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 told The Advocate in 2016.

As for why she remained silent as the allegations swirled, the performer responded that she wasn't in the habit of pouring her heart out to the tabloids.

'I’d said all I needed to say on that subject. I’m an old-fashioned gal who doesn’t feel it’s appropriate to hang out your laundry on the lawn,' she told the publication.

'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.'

She did go on to acknowledge, though, that 'sometimes it is difficult to just let something be what it is, especially when it’s unnecessary ugliness.'

In 2007, Chesney shut down the rumors and said they were simply 'not true.'

'I didn't have to prove to anybody that I wasn't. I didn't feel like I really did,' he said in a 60 Minutes.

Short-lived marriage: To the world's shock, just four months after tying the knot, in September 2005, she filed to annul her marriage to Chesney, citing 'fraud' as the reason (seen in 2005)

Bradley Cooper (2009-2011)

Like most of her high-profile relationships, the Judy star fell hard for another hunky costar.

Upon meeting the nine-time Academy Award nominee on set of their film Case 39 in 2009, Zellweger and the father-of-one found love.

While they both stayed tight-lipped about their time together, Cooper couldn't help but sing her praises in one interview.

'I just love her. I [loved] coming to work. I love acting with her. I can learn so much from her,' he told ET in 2010.

She told the outlet that he is 'a great, great actor' and admitted to being 'so excited' to get to 'work with him.'

They went on to move in together that same year, but parted ways in 2011.

Following the death of his father, Charles Cooper, she skipped the Golden Globes to be with him, according to People, who reported she was 'close to Cooper’s mom, Gloria.'

Sweet: Like most of her high-profile relationships, the Judy star fell hard for another hunky costar (seen in 2009)

Still friendly: Upon meeting the nine-time Academy Award nominee on set of their film Case 39 in 2009, Zellweger and the father-of-one found love (seen together in 2020)

Doyle Bramhall II (2012- 2019)

Unlike her other past lovers, rocker Doyle Bramhall II met Zellweger when they were just students at the University of Texas in the early nineties.

In 2012, two years after ending his marriage, they decided to give dating a try.

Though they never considered a romantic relationship during their college days, the two made by for lost time as they stuck by each other's sides from 2012 to 2019.

Doyle is known for his work in Arc Angels and for touring with Eric Clapton for six years.

Upon speaking about their romance in 2015, she gushed: 'Isn't he cute? He's a very sweet man.'

'I'm very, very happy right now,' the star told People.

According to the documents, obtained by E! News, he lived for free with her and she paid his credit card bills in the midst of his separation from his former spouse, Susannah Melvoin.

The site reports that Renee has been subbing the credit card fees which vary between $4,000 to $5,000 a month, with the court documents detailing that this a loan and a repayment is expected.

Renee is also said to have paid for Doyle's expenses in 2015 that added up to nearly $60,000.

During a hearing in Doyle's divorce from ex Susannah Melvoin, the judge ruled that Renee's income should not have any bearing on what the musician pays in spousal and child support to his estranged wife.

Doyle, who also dated Sheryl Crow, was married to Susannah from 1997 to 2010 and they have two daughters together.

According to Radar Online, his jealousy contributed to the end of their longtime relationship.

'She and Doyle built a happy home life together and they even discussed adopting a baby together,' a source told the outlet in 2016.

Ultimately, they 'drifted apart emotionally when they were separated for weeks at a time' and weren't 'able to rekindle the spark.'

The insider added: 'Renee hit her breaking point over the jealousy issues.'

Longtime love: Upon speaking about her romance with Doyle Bramhall II during a 2015 interview, she gushed: 'Isn't he cute? He's a very sweet man' (seen in 2014)

Ant Anstead (2021-present)

Anstead and Zellweger initially met while filming an episode of his series Celebrity IOU Joyride in April of 2021.

At the time, she was grieving the death of her publicist Nanci Ryder when she was watching Property Brothers with Brad Pitt as a guest star.

It was an HGTV show called Celebrity IOU, in which a famous person honors someone in his or her life by having the Property Brothers renovate their home. Brad had his makeup artist's garage revamped.

Zellweger wanted to help the two nurses who had looked after Ryder in the last years of her life: twin brothers named Jerome Cowan and Jerald Cowan.

In April of 2021, Renee was told about Celebrity IOU: Joyride which would feature British TV personality Anstead as he rebuilt classic cars back to their top shape.

Fate: Anstead and Zellweger initially met while filming an episode of his series Celebrity IOU Joyride in April of 2021

Happier than ever: After meeting her soulmate, a friend of the actress told People that Renee is 'head over heels' and has 'never been happier,' in a relationship

When asked by Harper's Bazaar if Zellweger thought Anstead was a gift from the late Ryder, she responded they 'joke about that.'

'She's always doing her best. It made me smile,' the star explained. 'It made me smile to think on this, yeah, the serendipity of it all.'

After meeting her soulmate, a friend of the actress told People that Renee is 'head over heels' and has 'never been happier,' in a relationship.

'She thinks this is the real deal. She's never been happier. They're a great couple,' the insider told the outlet. 'Sometimes two people just meet and click, and the timing is right.'

The source added: 'Renée is creative...and often goes for guys who think out of the box...Both of them are private and dislike public scrutiny, so they have that in common. He's a creative guy with lots of interests.'

Interesting meet cute: The couple met on the set of Celebrity IOU: Joyride, which Anstead was hosting

Two years: In April, the couple celebrated two years of dating

In a 2019 Vulture interview — shortly after she had split from Bramhall — she spoke about the pressure as a woman to be in a relationship.

'If you're not cherished by someone, if a man doesn't find you and treasure you, then your worth somehow comes into question. It's just the reality of being a lady,' she said.

Renee and Ant have been going strong since their fateful introduction.

'Ant is very happy with Renée. He really loves her,' an entertainment source recently told People.

Movie star: Zellweger is best known for starring in the 2001 movie Bridget Jones's Diary (seen above in character)

Additionally, the insider said they 'spend a lot of time at home' and have a 'very normal relationship.'

It was added that Anstead and Zellweger 'very much prioritize Hudson. They want him to be happy and comfortable.'

On their anniversary this spring, Ant celebrated 'two years of magic' with Renee by sharing a video to his Instagram account.

While they typically keep their relationship out of the spotlight, he praised her singing on St. Patrick's Day.

Supportive: While they typically keep their relationship out of the spotlight, he praised her singing on St. Patrick's Day

After a fan raved that Zellweger has the 'voice of an angel' on Twitter, her beau replied: 'She’s the best!!!'

In October, friends of the couple told Us Weekly that the duo were getting more and more serious.

​'They are so happy and super excited to be mapping out their long-term future together,' a source told Us Weekly.

Despite 'trying not to get too far ahead of themselves' when 'it comes to their exact arrangements,' their friends believe wedding bells are in their near future.

Sweet: In 2021, Anstead also praised her for being a 'good traveler' after visiting her on the set of The Thing About Pam, in Louisiana, during an interview with Entertainment Tonight

In January, he posted a photo of them dancing in the street under the moonlight

A month later, he shared a clip of her music video for Two Steps with C.M. Talkington, with the caption: 'Ren….. you are utterly brilliant! A beautiful and talented genius! The most gorgeous and classy lady who continues to effortlessly tackle inspiring and cool projects in your stride! The coolest human I know.'

In 2021, Anstead also praised her for being a 'good traveler' after visiting her on the set of The Thing About Pam, in Louisiana, during an interview with Entertainment Tonight.

Following his trip to visit her on set, he shared a rare selfie of them together as they kissed, with the caption: 'WOW there is something very special about New Orleans!'

'The late night wandering, the mind blowing history this nerd loves, the architecture, the blend of cultures, the food, the people, the smells and noises! All made made [sic] better by magical company to share it with,' he gushed.

Special occasion: It comes after Ant celebrated 'two years of magic' with his girlfriend Renee by sharing a video to his Instagram account in April

A month later, they spent Thanksgiving together at a game in New Orleans with his youngest.

In February 2022, he ton his Instagram followers that he was 'beaming with pride' over 'Ren’s latest role' in The Thing About Pam.

Last summer while speaking about the media attention surrounding their romance, she told The Sunday Times that she doesn't 'pay much attention to any of that.'

In regards to why she stays off social media, the Oscar winner said: 'I don't think it would be a good thing for me. I have a list of things I like to get done every day.'

Anstead was previously married to his first wife Louise from 2005 until 2017, and they welcomed a daughter and son named Amelie and Archie.

He went on to tie the knot with Christina Hall in 2018, and they welcomed their son Hudson, born in 2019, before divorcing in 2021.

Source: Daily Mail