Renée Zellweger's Dating History: From Jim Carrey to Ant Anstead

Jim Carrey

Zellweger and Carrey met in 1999 on the set of the Me, Myself and Irene and dated for one year before breaking up in 2000.

"You could see that he really flipped for her," director Bobby Farrelly said of the pair (here at the Los Angeles premiere of his film Man on the Moon in 1999).

In a 2020 interview, Carrey told Howard Stern, "She definitely was special to me, very special; I think she's lovely."

Jack White

Zellweger met White Stripes rocker White on the set of 2003's Cold Mountain, in which he had a small role as a troubadour. Although White preferred his hometown of Detroit to Hollywood hot spots, the couple quietly dated for more than a year and a half. After they split in September 2004, a source close to the actress told PEOPLE, "It was mutual. No scandal. No new relationships."

Kenny Chesney

Zellweger and country star Chesney initially met at the Concert of Hope tsunami relief telethon on Jan. 15, 2005, where Chesney performed and Zellweger answered telephones. Reportedly, Chesney already had eyes for his future bride before they met at the benefit concert. In fact, she was the inspiration behind his 1999 song "You Had Me from Hello," a play on the famous line, "You had me at hello," from Zellweger's breakout role in 1996's Jerry Maguire.

"When she [Renée] said that in the movie, it was like instant. I said, 'That could be a wonderful song,'" Chesney told USA Weekend back in 1999, per ABC News.

The public first learned of their relationship on April 29, 2005, when Zellweger brought Chesney a margarita and kissed him onstage at his concert in Jacksonville, Florida, as reported by ABC News. After knowing him for three months, PEOPLE confirmed the two tied the knot on May 9, 2005, in a small ceremony on the island of St. John in the U.S. Virgin Islands.

However, in September 2005, Zellweger filed to annul the marriage, citing "fraud" as the reason for the split. Both stars asked for privacy as news broke and never spoke of the marriage or separation.

Bradley Cooper

After meeting on the set of their 2009 film Case 39, Cooper and Zellweger struck up a relationship, getting serious enough to spend holidays with his family and for the actress to go shopping with his mom. Engagement rumors swirled as the stars stayed silent on their status, except for Cooper revealing to Entertainment Tonight in 2010, "I just love her. I [loved] coming to work. I love acting with her. I can learn so much from her."

Zellweger echoed Cooper's sentiments, telling ET, "[Bradley]'s a great, great actor. I just got so excited, not believing that I was going to go to work with him."

Though the two moved in together in fall of 2010, PEOPLE ultimately confirmed their breakup in March 2011.

Doyle Bramhall II

Zellweger's longest public relationship was with the musician, whom she dated from 2012 to 2019. They first met at the University of Texas in the '80s.

"Isn't he cute? He's a very sweet man," the actress told PEOPLE during a 2015 interview. "I'm very, very happy right now."

Speaking to PEOPLE in September 2019 following their breakup, the Judy star said of love, "[It] kind of stays. And that over time, even when you think it's gone, reflecting on it, it's still very much there. It's kind of great, actually."

Ant Anstead

In 2021, PEOPLE confirmed Zellweger was dating Wheeler Dealers star Anstead, who finalized his divorce from HGTV star Christina Hall (née Haack) in June 2021. TMZ was the first outlet to report on the new couple.

The pair first met while filming Anstead's Discovery+ series Celebrity IOU Joyride and made their relationship Instagram official in September 2021. By January 2022, Zellweger had met Anstead's children, which Anstead told PEOPLE went "great."

"I mean, Renée's so personable, and so great with people, and they've met a few times on FaceTime, so everybody was excited to finally get together," he said. "Of course, everybody got on famously. It's really nice."

The couple continue to spend time with Anstead's three children. In August 2022, Anstead posted a photo on Instagram of his son Hudson wearing Zellweger's oversized coat after a day at the beach.

"When a stroll to the beach (in clothes) ends with a fully soaked toddler...... said toddler obviously walks home in the missus coat," Anstead captioned the series of photos and videos from their father-son outing.