The rocky road to love. Jim Carrey’s dating history is filled with high-profile celebrities, from Renée Zellweger to Jenny McCarthy.

The Yes Man actor has been married twice: to Melissa Womer from 1987 to 1995 and to Lauren Holly from 1996 to 1997. Carrey shares daughter Jane, who competed on American Idol in 2012, with his first wife.

After his second divorce, the Eternal Sunshine of the Spotless Mind star moved on with Zellweger, with whom he worked on 2000’s Me, Myself and Irene. The duo were briefly engaged but never made it down the aisle.

“She was special to me, very special. I think she’s lovely,” the Golden Globe winner said of his ex during a July 2020 interview on The Howard Stern Show. “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.”

At the time, nearly two decades after he and the Bridget Jones’s Diary actress called it quits, Carrey confessed that he considered her “the great love of [his] life.” Zellweger, for her part, previously reflected on her “unexpected” connection with the Memoirs and Misinformation writer.

“It was just a really natural thing to want to be around each other,” she told Entertainment Weekly in June 2000. “And we didn’t see each other for a few months after we finished the picture — or really speak even — and I just noticed his absence significantly. It just felt like, ‘Wow, I really miss him.’”

After splitting from the Judy star, Carrey sparked a long-term relationship with McCarthy in 2005 following her divorce from John Asher. The former View cohost and the director welcomed son Evan in 2002.

The Truman Show alum and the Scream 3 actress were together for five years before Us Weekly confirmed their split in April 2010. “I’m so grateful for the years Jim and I shared together,” McCarthy told Us in a statement at the time. “I will continue to be in his daughter’s life and will always keep Jim as a leading man in my heart.”

Shortly before their breakup, McCarthy opened up about why she and Carrey didn’t feel pressured to get married.

“We say ‘never,’ but I don’t know,” she told Us in February 2010. “Maybe for tax purposes, someday, when we are old.”

Things between the former couple soon turned messy, as the Masked Singer personality claimed that her son felt abandoned by Carrey.

“I’ve tried to ask [Jim] numerous times [to see Evan] because my son still asks,” she said on The Howard Stern Show in June 2012. “I think that sometimes people need to take a real break from each other. … But I still love him. I think you can love people from a distance and respect him. But as a mother, you just hope when you have a relationship with someone, it has nothing to do with the child when you break up.”

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At the time, the Bruce Almighty actor told Us in a statement that he still cared deeply about Evan, noting, “I will always do what I believe is in the best interest of Evan’s well-being. It’s unfortunate that Evan’s privacy is not being considered. I love Evan very much and will miss him always.”

Scroll down for a closer look at Carrey’s relationship history:

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