10 Celebrities Who Remarry More Than Once To Find True Love

Margot Nolan
May 26, 2022
May 26, 2022

Despite what the cynical people might tell you, true love does exist. Unlike fairy tales, in real life, we struggle to find our perfect match. Our soul mates. Our one true love.
But that doesn’t mean we need to stop trying. Most of us have an inner need to connect to another human being on every level. It lessens our loneliness, even just for a while. Sometimes, this can even rush us into marriage a little too soon.
Unfortunately, there’s no book on how to find your true love, lest marry them. That means it might take us a few tries before we find our Mr. or Mrs. Right.
This is especially true for celebrities. It’s lonely at the top, and marrying someone might bring some solace to their lives. Until it doesn’t, and they call it quit, going back in search of the next “true love”.
While there are definitely more, we give you the 10 celebrities who remarry more than once to find true love.

#10 Jennifer Lopez: 3 marriages, 2 failed engagements.

Source: © Invision/Invision/East News

Jennifer Lopez has married three times, with two failed two engagements. Her first two marriages, to Ojani Noa and Cris Judd, lasted less than a year. Her third marriage was to Marc Anthony, 5 months after calling off her engagement with Ben Affleck. Unfortunately, their marriage also ended 7 years later.
Jennifer still didn't give up on love, opening her heart and engaged to baseball player Alex Rodriguez. The lovebirds called it quit two years later.
But Jennifer might have found true love again. Recently, she revived Bennifer, and rekindled her relationship with Ben Affleck. We're hoping that this time Ben will be "the one" for her.

#9 Demi Moore: 3 marriages.

Source: © Sebastien Courdji/KCS/East News

Demi Moore has tried her hand at marriage three times, all of which have ended in divorce. Her first spouse, singer Freddy Moore, was 12 years her senior. The couple divorced two years after saying, "I do."
After that, Demi became engaged to actor Emilio Estevez. They had intended to marry in 1986, but keep postponing the wedding. Instead, her actual second marriage was to Bruce Willis. The couple lasted for 13 years and had three kids.
Moore tried marriage again with Ashton Kutcher, who was 15 years her junior. Their marriage did not work out well, and they divorced after 6 years.

#8 Eva Longoria: 3 marriages

Source: © Gilbert Flores/Broadimage/Broad Image/East News

Love did not come readily to Eva Longoria. She previously had two unsuccessful marriages, one with actor Tyler Christopher that barely lasted two years. Her second marriage with Tony Parker lasted somewhat longer, four years.
Eva is currently happily married to José Bastón, a Mexican businessman, with whom she has a son, Santiago.

#7 Frank Sinatra: 4 marriages, 2 failed engagements.

Source: © East News

Frank Sinatra’s first marriage, to Nancy Barbato, lasted 12 years and resulted in three children. Sinatra then married Ava Gardner the same year he divorced Barbato. His second marriage, however, proved to be quite tumultuous, and Ava filed for divorce three years later.
After that, Sinatra had two canceled engagements. Until 1966, when he married Mia Farrow, which resulted in his shortest marriage. The third time wasn't the charm for Frank, apparently.
After three failed marriages, Frank ultimately married Barbara Marx, with whom he remained married until his death.

#6 Billy Joel: 4 marriages

Source: © Robert Hepler/Everett Collection/East News

Billy Joel has married four times. He married his fourth and final wife, Alexis Roderick, when he was 65 years old.
His previous marriages are to Elizabeth Weber Small, Christie Brinkley, and Katie Lee. They, however, did not deter him from believing in real love and giving marriage another opportunity.

#5 Lisa Marie Presley: 4 marriages

Source: © AXELLE/BAUER-GRIFFIN/East News

Lisa is 54 years old and is still not married, but not for a lack of trying. The most recent divorce from her fourth spouse, guitarist and music producer Michael Lockwood, was finalized in 2021.
She previously married Danny Keough and had two children with him, a boy and a daughter. Her second marriage was to Michael Jackson. They attempted to reconcile after their divorce, and Lisa even flew to different areas of the world to be with him. But regrettably, reconciliation never happened to them.
Lisa was engaged to musician John Oszajca in 2000, but called it off to marry Nicolas Cage. Unfortunately, their marriage was also short-lived.

#4 Gary Oldman: 5 marriages

Source: © Mary Evans/Allstar/Graham Whitby Boot./East News

Almost all of Oldman's marriages ended in divorce. His first two marriages, to Lesley Manville and Uma Thurman, lasted barely two years each. His third, to Donya Fiorentino, lasted four years. Alexandra Edenborough, an English singer and actress, was Oldman's fourth wife, although they divorced after six years together.
Gary is presently married to Gisele Schmidt, his fifth wife, and who knows, maybe the fifth time may be the charm.

#3 Pamela Anderson: 5 or 6 marriages, 1 failed engagement.

Pamela famously married Tommy Lee when she was 28 years old, but their marriage lasted only three years. She then became engaged to Marcus Schenkenberg, but they were never married. Her actual second marriage was to Kid Rock, and it, too, did not end happily ever after.
Pamela married the same person twice; she and Rick Salomon exchanged vows on her third and fourth weddings. But even their second attempt failed, just as disastrous as their first.
Anderson gave it another shot and married Jon Peters. However, following their divorce, she claimed that they were never officially married. Legally, though, she married for the sixth time to her bodyguard, Dan Hayhurst, but they also divorced after about a year on January 21, 2022.

#2 Billy Bob Thornton: 6 marriages, 1 failed engagement.

Billy has been married six times. Most of his marriages last between two and four years. His previous spouses include Toni Lawrence, Cynda Williams, Pietra Dawn Cherniak, and Angelina Jolie.
He was also engaged to actress Laura Dern for two years, but this clearly didn’t go anywhere.
Billy tried again after several unsuccessful marriages and began dating Connie Angland in 2002. While we might think that the marriage life isn't for him, he nonetheless said "I do" to Connie in 2014. And they are still married today.

#1 Elizabeth Taylor: 8 marriages

Elizabeth was married eight times to seven different husbands. Almost all of her marriages lasted from 8 months to 6 years.
Her longest marriage lasted ten years with Richard Burton, and they married again 16 months after their initial divorce. Unfortunately, their second attempt did not even survive a year.
Yet, Elizabeth never once gave up on finding her true love, even writing that she was meant to be a wife, mother, and friend.

Share this article