Renee Zellweger’s Dating History: From Jim Carrey and Kenny Chesney to Bradley Cooper and More

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Renee Zellweger’s Dating History: From Jim Carrey and Kenny Chesney to Bradley Cooper and More

She’s a big star with an even bigger love life! Renée Zellweger has captivated audiences since the early ‘90s, and she’s been winning over men’s hearts just as long. The Chicago star, who is from Katy, Texas, has made a name for herself in Hollywood with success on the big screen and two Oscar-winning performances. Off screen, she has lived an equally as exciting life, getting engaged once, married once and having many high-profile romances through the years. Despite calling off their engagement in 2000, Jim Carrey continues to speak highly of the Cinderella Man actress, whom he calls the “great love” of his life. “She was special to me, very special. I think she’s lovely,” the Mask actor said on The Howard Stern Show in July 2020. “I don’t regret — I don’t have those things. But I do appreciate the people that have come through my life for the good that they gave me … but I don’t pine for anybody, it’s not that kind of situation. It’s just my way of saying, ‘There was a very important thing there,’ and to recognize that.” Zellweger walked down the aisle in a private beach ceremony just five years after splitting from Carrey after a whirlwind romance with Kenny Chesney. The pair split after four months of marriage and the actress was quickly linked to multiple Hollywood heartthrobs, many of which she never actually dated. [jwplayer ujdNpiOr-l3ahXupL] During an interview with W magazine in November 2007, Zellweger and longtime friend George Clooney joked about how long they’ve been married as fans continued to ship them as a couple. "35 [years],” Clooney said, while Zellweger joked, “We’ve been married 28.” The Ocean’s Eleven star fired back, “Twenty-seven. We lived together the first year. It was a lot of fighting.” The My Own Love Song actress chimed in, “But we saved on rent. And I fed the dogs and pigs. I vacuumed too.” Clooney added, “That’s true. I was a younger leading man, and she was an ingenue.” The same year, Zellweger was rumored to be seeing Paul McCartney, but the actress denied they were anything more than acquaintances. "He's as lovely as I expected. We have mutual friends. The crush and I have mutual friends,” she told Harper’s Bazaar in 2007. Scroll down to see which men Zellweger has dated over the years: [podcast_block]

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Sims E. Ellison

Zellweger dated Ellison, who was a musician in their home state of Texas, for five years before splitting in 1993. Two years later, the Pariah guitarist died by suicide. The Jerry Maguire star attended the funeral and gave a eulogy for her lost love.

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Rory Cochrane

The Bridget Jones's Diary star was reportedly dating her Empire Records costar while filming the 1995 hit.

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Jim Carrey

The Ace Ventura Pet Detective star met Zellweger on the set of Me, Myself and Irene in 1999. They got engaged that same year, but the romance quickly fizzled out, ending in late 2000.

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Jack White

The White Stripes musician and the Oscar winner began dating in 2002 after meeting on the set of Cold Mountain. Zellweger played Ruby Thewes in the drama, while White played a troubadour and sang on the soundtrack. They split less than two years later in September 2004.

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Kenny Chesney

The country crooner and the Judy actress tied the knot in May 2005 after meeting four months prior at NBC’s “Concert of Hope” telethon. Their marriage was annulled just four months after they said, “I do,” with the pair listing “fraud” as the reason for their split. Chesney told Playboy in 2009 that there wasn’t really any legal issues in their relationship, but it was the easiest way to end the marriage.

“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,” he said at the time. “The best thing we could put in there was fraud. So I said, ’All right, do it. Whatever.'”

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John Krasinski

Zelleweger was rumored to be dating The Office alum in 2007 when they were spotted attending a comedy show and walking together in North Carolina while on location for their film Leatherheads.

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Dan Abrams

The former MSNBC correspondent and the Texas native sparked relationship speculation in 2009 when they were seen having dinner together and going to a wine shop in Manhattan.

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Bradley Cooper

The actors met on the set of their thriller Case 39 in 2006, but their romance didn’t bloom until the summer of 2009. Us Weekly confirmed in March 2011 that the pair had called it quits after less than two years of dating.

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Doyle Bramhall II

Zellweger began dating the musician in 2012. Five years into their romance, the What/If actress gushed over her man, exclusively telling Us in June 2017, “He’s a very special person.” The couple reportedly split two years later in May 2019.

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Ant Anstead

News broke in June 2021 that the actress is dating the Wheeler Dealers alum after meeting on the set of his upcoming Discovery+ show, Celebrity IOU Joyride, earlier in the month. The new romance came the same month that Us confirmed Anstead finalized his divorce from Christina Haack nine months after their split.