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Bright Side

9 Celebs Who Had Multiple Marriages on the Search for Their True Soulmate

In movies, most of the time, finding true love is portrayed as an easy task. 2 people meet for the first time and they instantly fall head over heels for each other. But, believe it or not, more than 172 divorces happen in the time span it takes to watch an average rom-com movie, and reality has never hit us so hard.

People who give love 2, 3, or even 10 chances, have real courage. And we at Bright Side believe that even though it might be hard to find “the one,” it’s always worth fighting for it.

1. Jennifer Lopez

Jennifer Lopez tried marriage 3 times and called off 2 engagements that almost ended up in marriage for her. Her first 2 marriages, to Ojani Noa and Cris Judd, were short-lived and didn’t even last a year. Speaking on her 2 first marriages, the singer admitted, “One was 9 months and one was 11 months, so I don’t really count those.”

She said “I do” for the third time to Marc Anthony 5 months after breaking her engagement with Ben Affleck, but their marriage ended 10 years later.

OnTheJLo via Grosby Group/Grosby Group/East News

Lopez didn’t give up on love and, once again, opened her heart to baseball player Alex Rodriguez. They got engaged, and even though their relationship seemed strong, they ended things just 2 years later.

After splitting up with Rodriguez, Lopez got back together with Affleck, 17 years after their breakup. We hope this time the actor will be “the one” for her.

2. Billy Bob Thornton

Chris Pizzello/Invision/AP/East News

So far, Billy has been married 6 times, and almost all of his marriages were short, spanning from 2 to 4 years. He was married to Melissa Lee Gatlin, Toni Lawrence, Cynda Williams, Pietra Dawn Cherniak, and Angelina Jolie. He was also engaged to actress Laura Dern for 2 years.

After many failed marriages, Billy tried again and started dating Connie Angland in 2002. And although on one occasion he said that marriage doesn’t work for him, he still said “I do” to Connie in 2014, and they are still married today.

3. Pamela Anderson

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Pamela tied the knot for the first time with Tommy Lee when she was 28 years old, but their marriage only lasted for 3 years. After their divorce, Pamela got engaged to Marcus Schenkenberg, but they didn’t make it to the altar. Her second marriage was to Kid Rock, and this one, too, didn’t have a happily ever after ending.

Pamela’s third and fourth marriages were to the same man — Rick Salomon. Even though they tried 2 times, and had a chance to make up for their mistakes, their second try had the same outcome as the first one. Anderson decided to try again and married Jon Peters. However, after their separation, she claimed that they were never legally married.

Anderson was legally married for the fifth time to her bodyguard, Dan Hayhurst but, unfortunately, they separated after a year or so on January 21, 2022.

4. Frank Sinatra

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Frank’s first marriage was to Nancy Barbato, with whom he had 3 children. Their union lasted for 12 years, but the same year of their divorce, Sinatra tied the knot with Ava Gardner. However, their marriage turned out to be very turbulent and 3 years later, Ava filed for divorce.

After that, Sinatra had 2 called-off engagements as well, but even so, he didn’t lose hope. In 1966, he married Mia Farrow, with whom he had the shortest marriage. Turns out the third time wasn’t quite a charm for Frank.

After 3 marriages that ended in divorce, Frank finally married someone for life, Barbara Marx, with whom he stayed together until his final days.

5. Demi Moore

Sebastien Courdji/KCS/East News

Demi Moore gave marriage a chance 3 times so far, but all 3 ended in divorce. Her first husband was singer Freddy Moore, who was 12 years older than her. The pair separated 2 years after they said “I do” and after some time, Demi got engaged with actor Emilio Estevez. They planned to marry in 1986 but called off the engagement.

A year later, Demi married Bruce Willis with whom she had 3 daughters. They divorced 13 years later, and Moore gave marriage a try one more time with Ashton Kutcher, who was 15 years younger than her. Their marriage didn’t work and, after 6 years, they divorced.

6. Elizabeth Taylor

Collection Christophel/Collection Christophel/East News

Elizabeth Taylor was married 8 times to 7 different husbands. Almost all of her marriages were short, spanning from 8 months to 6 years. Her longest marriage of 10 years was with Richard Burton, and 16 months after their first divorce, they tied the knot again. Unfortunately, their second try didn’t even last a year.

7. Billy Joel

Robert Hepler/Everett Collection/East News

Billy Joel married his fourth wife, Alexis Roderick, to whom he said “I do” when he was 66 years old. His former marriages with Elizabeth Weber Small, Christie Brinkley, and Katie Lee that ended in divorce didn’t stop him from believing in true love and giving marriage a chance once again.

8. Eva Longoria

Gilbert Flores/Broadimage/Broad Image/East News

Eva is now happily married to Mexican businessman José Bastón, with whom she had her first child, Santiago. But love didn’t come very easily for her. Before José, Eva had 2 failed marriages with actor Tyler Christopher that lasted only 2 years and a 4-year long marriage with Tony Parker.

9. Gary Oldman

Mary Evans/Allstar/Graham Whitby Boot./East News

Almost all of Gary Oldman’s marriages were short-lived. His first 2 marriages to Lesley Manville and Uma Thurman lasted only 3 and 2 years, respectively, and his third marriage to Donya Fiorentino lasted for 4 years. Oldman’s fourth wife was the English singer and actress, Alexandra Edenborough, but they divorced after 7 years together.

Oldman is currently married to his fifth wife, Gisele Schmidt, and who knows, maybe the fifth time will be his lucky one.

What do you think, why do some people have to tie the knot several times before finding “the one?” If you lucked out with your first marriage, what is your secret?

Please note: This article was updated in January 2023 to correct source material and factual inaccuracies.
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