By Megan Riedlinger
10:42am PDT, Apr 9, 2022
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Jennifer Lopez and Ben Affleck are engaged once more, J.Lo's rep confirmed to People on April 8, 2022. To celebrate, Wonderwall.com is rounding up the celebrity serial romantics who've been engaged or married five times (or more!) starting with Ben's bride-to-be … Jennifer Lopez's recent movie "Marry Me" covers a topic she's pretty well versed in — marriage! J.Lo has been engaged not once, not twice, but six times — first to waiter Ojani Noa (husband No. 1), then to dancer-choreographer Cris Judd (husband No. 2), after that infamously to movie star Ben Affleck (though they called off their 2003 wedding), then to the father of her twins, salsa singer Marc Anthony (husband No. 3), and then to retired MLB star Alex Rodriguez, from whom she split in 2021 before reuniting with Ben later that year. In April 2022, Jen confirmed her engagement to Ben in her newsletter and showed off her new, green diamond ring.
Keep reading to see more serial romantics…
RELATED: Shortest celebrity marriages
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Here's one that might surprise you: Billy Bob Thornton has been engaged more times than Jennifer Lopez! The actor has proposed to seven different women over his lifetime. Not all of them resulted in marriage, however. He popped the question to Laura Dern before leaving her for and subsequently proposing to and marrying Angelina Jolie — but the others made it down the aisle with him: Melissa Lee Gatlin, Toni Lawrence, Cynda Williams, Pietra Dawn Cherniak and, most recently, Connie Angland, to whom he's still wed.
RELATED: Celebrity weddings of 2022
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Our next star had her first engagement at a very young age — 16! Drew Barrymore's then-beau, Leland Hayward III, was her first fiancé, though it was short-lived. She was later engaged to Jamie Waters, ex-husbands Jeremy Thomas and Tom Green and, most recently, ex-husband Will Kopelman, with whom she shares two daughters.
RELATED: Celebs who got engaged in 2022
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Richard Pryor called five different women his wife over his lifetime, but tied the knot seven times! Confused? Here's the scoop: He first wed Patricia Price, then Shelley Bonis, followed by Deborah McGuire, Jennifer Lee and Flynn Belaine — whom he subsequently divorced and remarried. Then, after a second divorce from Flynn, he remarried Jennifer!
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Pamela Anderson just ended her sixth — or maybe fifth? — marriage in January 2022. Let us explain… The star's first marriage took place early in her career: She famously wed Tommy Lee after knowing him for just four days. The iconic couple were together for three years before calling it quits. Pamela went on to marry another musician, Kid Rock. That union lasted four months. Then she wed professional poker player Rick Salomon. That marriage was annulled weeks later, though they remarried a few years later — technically making him her third and fourth husband. They split after a few months, once again, and Pamela had a wedding ceremony with producer Jon Peters in 2020. That lasted a few days, and it was later revealed it may not have been a legal union. Most recently, she tied the knot with bodyguard Dan Hayhurst in December 2020; they split a year later.
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Nicolas Cage joined this list in February 2021 when he wed his fifth wife, Riko Shibata. Prior to that, he'd famously married Patricia Arquette. A quickie marriage to Lisa Marie Presley followed (it lasted mere months), then he wed Alice Kim. His fourth marriage, to Erika Koike, was his shortest — it lasted just four days in 2019.
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"Golden Girls" star Rue McClanahan had her fair share of husbands — six! Her spouses, in order, were Tom Bish, Norman Hartweg, Peter DeMaio, Sam Fisher, Tom Keep and Morrow Wilson — to whom she was still wed at the time of her death in 2010.
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Next up? Lady's man David Foster. The producer and composer was first married to Linda Thompson, then Rebecca Dyer and then B.J. Cook. His fourth marriage, to model and "The Real Housewives of Beverly Hills" star Yolanda Hadid, also ended in divorce. He wed his fifth wife, singer-actress Katharine McPhee, in 2018.
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Lisa Marie Presley's love life was quite busy. Her first engagement — to musician Danny Keough — led to marriage and two kids: actress Riley Keough and the late Benjamin Keough. Her next round of romances are perhaps her most infamous — she married Michael Jackson then Nicolas Cage. She then accepted a proposal from John Oszajca but they didn't make it down the aisle. Her fifth and most recent marriage, to musician Michael Lockwood, resulted in two more kids — twin daughters Harper and Finley — and a bitter divorce.
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Legendary talk show host Larry King, who passed away in 2021, left a legion of would-be widows. He married seven different women in eight ceremonies over the years, starting with Freda Miller, his high school sweetheart. That marriage was annulled when their parents disapproved. He followed it up with a rash of nuptials — first to Annette Kaye, then Alene Akins, then Mickey Sutphin. He remarried Arlene next, only to divorce her again and marry Sharon Lepore a few years later. Next up was Julie Alexander, followed by Shawn Southwick. They were in the midst of a divorce when he died.
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Joan Collins' current husband, Percy Gibson, is her fifth spouse. The "Dynasty" icon first married fellow actor Maxwell Reed — the union lasted four years — before marrying Anthony Newley in the '60s and Ron Kass in the '70s. She wed and divorced Peter Holm in the '80s before saying "I do" with Percy in 2002.
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The late, great Kenny Rogers was married five times. He first wed Janice Gordon in the late '50s, then wed Jean Rogers. Next up was Margo Anderson, then actress Marianne Gordon. In 1997, he said "I do" for the last time to Wanda Miller, who became a widow in 2020 when he passed away.
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Another Hollywood starlet who headed to the chapel quite a few times? Rita Hayworth, who first wed Edward C. Judson. She then married famed filmmaker Orson Welles, followed by Prince Aly Khan, a Pakistani diplomat. Actor Dick Haymes was next, followed by James Hill, her final husband. That lasted just three years.
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Though he's been happily married to Helen Morris since 1999, filmmaker Martin Scorsese had four wives before her. He first wed Laraine Marie Brennan, then Julia Cameron. That marriage was followed up by a vow exchange with actress Isabella Rossellini. His fourth wife was Barbara De Fina.
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Elizabeth Taylor famously starred in "Father of the Bride" in 1950 and became a bride herself eight times out of 10 proposals. She was engaged to William Pawley Jr. first, but her second engagement — to hotel heir Conrad Hilton Jr. (Paris Hilton and Nicky Hilton's great uncle) — was her first marriage. Actor Michael Wilding became husband No. 2 and engagement No. 3. producer Mike Todd was next, followed by singer-actor Eddie Fisher. Liz then married and divorced actor Richard Burton — twice — and wed then divorced future senator John Warner. Engagements to Mexican lawyer Victor Luna and New York businessman Dennis Stein followed, and Liz walked down the aisle for the last time with construction worker Larry Fortensky.
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Just like e-wife Jennifer Lopez, Marc Anthony has also been engaged five times! The singer started down his romantic road with a failed engagement to actress Claudette Lali then ended up having two quick marriages back to back — first with actress Maria Von Ritchie Lopez then with former Miss Universe Dayanara Torres. J.Lo became his third wife. He followed that with a brief marriage to model Shannon De Lima.
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"Full House" star Jodie Sweetin has enjoyed five engagements. In January 2022, the actress revealed the happy news that boyfriend Mescal Wasilewski had just popped the question. That engagement was No. 5. She was previously engaged to Shaun Holguin, Cody Herpin, Morty Coyle and Justin Hodak, with the first three of those resulting in marriages.
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Did you know Gary Oldman has been engaged six times? Yep, and the actor has been married five times — to singer Alexandra Edenborough, Donya Fiorentino, Uma Thurman, Lesley Manville and, most recently, to current wife Gisele Schmidt. One of this engagements — to actress Isabella Rossellini — didn't result in marriage.
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The late Zsa Zsa Gabor said "I do" nine times! Yep, she happened to be one of the most married stars ever. Her first marriage took place back in 1935 when she exchanged vows with Burhan Asaf Belge. She later wed Conrad Hilton, George Sanders, Herbert Hutner, Joshua S. Cosden Jr., Jack Ryan, Michael O'Hara, Felipe de Alba and, finally, Frederic Prinz von Anhalt, whom she made a widower upon her death in 2016.
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Johnny Depp doesn't have a great batting average when it comes to successful engagements. The actor has proposed five times but only made it to the altar twice — first with makeup artist Lori Anne Allison in the '80s and more recently with actress Amber Heard in 2015. Over the years, he proposed to Sherilyn Fenn, Jennifer Grey and Winona Ryder — and was also rumored to be engaged at one point to Vanessa Paradis, the mother of his kids, Lily-Rose and Jack.
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The late Mickey Rooney's first marriage, to Ava Gardner, only lasted a year — leaving him free to get married seven more times! He next wed Betty Jane Phillips, then Martha Vickers. Next up was actress Elaine Mahnken, then another actress, Barbara Ann Thomason, who was murdered by a man with whom she was having an affair. This led to Mickey to marry Barbara's best friend, Marge Lane, in a union that didn't last a year. Carolyn Hockett was his next wife, then Jan Chamberlin, from whom he separated two years before his death in 2014.
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Hollywood starlet Lana Turner, who died in 1995, said "I do" eight times. Her first union, to Artie Shaw, lasted just four months. Then she wed Joseph Stephen Crane, only to have that one annulled. They later remarried and had a daughter together but divorced once more. Henry J. Topping was her next husband, then came Lex Barker and Fred May. Robert Eaton and Ronald Dante were her final two spouses.
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The late Dennis Hopper's five marriages include one that lasted only eight days. He first wed Brooke Hayward then followed that up with an infamous eight-day marriage to singer Michelle Phillips. Daria Halprin was wife No. 3, then came Katherine La Nasa and, finally, Victoria Duffy, from whom he split just months prior to his death in 2010.
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Former boxer-turned-grill mogul George Foreman proposed five different times! Though he's been married to current wife Mary Joan Martelly since 1985, he previously was wed to Adrienne Calhoun, Cynthia Lewis, Sharon Goodson and Andrea Skeete.
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Jennifer O'Neill is a model-turned-actress who rose to fame in the '60s — the same decade she became a wife for the first time. At 17, she married Dean Rossiter. Next, she wed Joseph Koster, then Nick De Boia, then Jeff Barry. The same year she divorced Jeff, she wed John Lederer, then when that ended, she married Richard Alan Brown. Next came Neil L. Bonin, though that marriage was annulled a year later, which allowed her to marry Richard — again — in the '90s. That second go-round didn't fare better than the first and they split, which freed her up to marry Mervin Disney Louque Jr. in 1996. They're still husband and wife.
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Another repeat offender? James Cameron, who's been married a total of five times. The director first wed Sharon Williams in the late '70s, followed by Gale Anne Hurd in the '80s. The year he split from Gale, he wed director Kathryn Bigelow, though they were divorced two years later. Actress Linda Hamilton his next wife, but their marriage only lasted two years. He wed his fifth and current wife, actress Suzy Amis, in 2000.
