These Celebrities Have All Been Engaged 4 Or More Times

Bella Thorne

So Bella Thorne’s dating history is a bit of a puzzle, with many false reports swirling around her high-profile (and sometimes controversial) relationships. On May 26, she announced she got engaged to producer Mark Emms, but this isn’t the first time!

Before Emms, she was engaged to her ex Benjamin Mascolo for about a year before they split up in 2022. Before him, her ex Mod Sun claimed that the two got engaged, married, and divorced within 15 months, per People. (But official documents have never been found!)

Those are the three confirmed engagements, with many outlets reporting that she was also engaged to exes Tana Mongeau and Gregg Sulking, but those seem to be rumors.

Marc Anthony – Engaged 5 Times

Marc Anthony just got engaged to former Miss Universe Paraguay Nadia Ferreira. This marks his fifth engagement. The singer has been married three times. Anthony’s first engagement was to actress Claudette Lali, though the two never made it down the aisle. The singer was married to Dayanara Torres from 2000-2004, Jennifer Lopez from 2004-2014, and Shannon De Lima from 2014-2017. 

Julia Roberts – Engaged 4 Times

Despite being married to Daniel Moder for more than 20 years, Julia Roberts was engaged quite a few times before she met her now-husband, with whom she shares three children. Roberts was first engaged to her Steel Magnolias co-star Dylan McDermott before they broke up in 1990. Then she was engaged to Kiefer Sutherland. Roberts called off her wedding to Sutherland mere days before they tied the knot. Then, Roberts was married to Lyle Lovett for roughly two years before their divorce in 1995.  

Jodie Sweetin – Engaged 5 Times

Full House star Jodie Sweetin has just announced her engagement to Mescal Wasilewski after four happy years together — but it isn’t the first time someone has asked her to tie the knot. Sweetin was first engaged to Shaun Holguin, whom she married in 2002, then Cody Herpin, whom she married in 2007, then Morty Coyle, whom she married in 2012. Her most recent engagement — before Wasilewski popped the question — was to Justin Hodak, in 2016 . 

Jennifer Lopez – Engaged 6 Times

Jennifer Lopez’s first fiancé was Ojani Noa, after which she accepted a proposal from and briefly married backup dancer Cris Judd. After they split, she got engaged to Ben Affleck (pictured here), but the couple broke up just before the wedding and she soon moved on with Marc Anthony, getting engaged and married in a whirlwind in 2004. They split in 2014 and Alex Rodriguez proposed to Lopez in 2019 after two years of dating. Now, Lopez is engaged (again) to Ben Affleck.

Brad Pitt – Engaged 4 Times

Brad Pitt first proposed to girlfriend Jill Schoelen before he made it big, but she broke things off after leaving town to shoot a movie. Then, he proposed to the other half of his ultimate ’90s pairing, Gwyneth Paltrow (pictured here), before they went their separate ways in 1997. By 2000, he had proposed to Jennifer Aniston and was walking down the aisle. And while they split in 2005, it wasn’t until 2014 that he made it official with his fifth and final (so far) fiancée Angelina Jolie, who filed for divorce in 2016.

Drew Barrymore – Engaged 5 Times

Drew Barrymore’s first engagement was at the very young age of 16, to Leland Hayward III, but it only lasted a few months. Actor Jamie Waters was another one-time fiancé of Barrymore’s, but third fiancé Jeremy Thomas became the first to actually become her husband. Barrymore married Thomas when she was just 19 years old (and he was 31 years old) and the marriage was called off within the month. It was a few more years before she married Tom Green at age 26 in a marriage that lasted one year, and another decade-plus before she married the father of her children Will Kopelman (pictured here) in 2012. The couple has since split.

Elizabeth Taylor – Engaged 10 Times

Okay, this is the big one, so we’ll run through them quickly. Elizabeth Taylor’s first fiancé was William Pawley Jr.; her second was Conrad Hilton, Jr., who was also her first husband. Actor Michael Wilding was fiancé #3 and husband #2, and producer Mike Todd the next, but their marriage ended in tragedy when he died in a plane crash. Her fifth fiancé was Todd’s close friend Eddie Fisher, and she also went on to famously be engaged and married to Richard Burton (twice, pictured here), politician John Warner, and construction worker Larry Fortensky. Rounding out her final two engagements are Victor Luna and Dennis Stein, both of whom had their engagement rings accepted by Taylor but later called it off. 

Lisa Marie Presley – Engaged 5 Times

Elvis Presley’s daughter Lisa Marie Presley had a legendary love life, first getting engaged to and marrying Danny Keough with whom she had kids Riley Keough and Benjamin Keough. She ultimately ended her marriage to Keough and next married Michael Jackson (pictured here), staying with him for two years before they split. Before her next marriage to Nicolas Cage, she became briefly engaged to John Oszajca, but left him for fiancé #4: when Cage filed for divorce a few months into their marriage, Presley moved on to Michael Lockwood, with whom she now shares twin girls Harper and Finley. She filed for divorce from Lockwood in 2016. 

Paris Hilton – Engaged 4 Times

Paris Hilton happily accepted a marriage proposal from boyfriend Carter Reum in 2021 and though she’s never been married before, she does have three past engagements: most recently, to Chris Zylka (pictured here), and previously to Greek socialite Paris Kassidokostas-Latsis and model Jason Shaw.

Billy Bob Thornton – Engaged 7 Times

Billy Bob Thornton’s first three marriages all lasted two years: to Melissa Lee Gatlin in 1978, Toni Lawrence in 1986, and Cynda Williams in 1990. In 1993, he married model Pietra Dawn Cherniak, who filed for divorce in 1997. Thornton was then engaged to Laura Dern before leaving her and proposing to Angelina Jolie (pictured here), to whom he was also only married for two years. He met his current wife Connie Angland in 2003, and married her in 2014.

Christie Brinkley – Engaged 4 Times

Model Christie Brinkley has been engaged and married four times, though she’s currently single: first, she was married to artist François Allaux for eight years, then musician Billy Joel (pictured here) for nine years. During that marriage, she was proposed to by Richard Taubman — she accepted and married him later that year, though they split a year later and she moved on to architect Peter Cook, to whom she was married for 11 years before announcing their separation. 

Demi Moore – Engaged 4 Times

Demi Moore’s first marriage to Freddy Moore earned her her famous last name and lasted five years, after which she quickly became briefly engaged to St. Elmo’s Fire co-star Emilio Estevez (pictured here). By the following year, she was engaged to Bruce Willis, to whom she was then married for 11 years. After they separated in 1998, Ashton Kutcher wasn’t her first rebound boyfriend but he was the next to get down on one knee, marrying Moore in 2005 before they split in 2011.

Gary Oldman – Engaged 6 Times

Gary Oldman has been married to current wife, writer Gisele Schmidt (pictured here), since 2017. Before that, he was married to singer Alexandra Edenborough for seven years, Donya Fiorentino for four years, Uma Thurman for two years, and Lesley Manville for three years. Between marrying Fiorentino and Thurman, he was briefly engaged to actress Isabella Rossellini.

David Foster – Engaged 5 Times

David Foster proposed to his current wife Katharine McPhee (pictured here) in 2018, three years after he and Real Housewives of Beverly Hills star Yolanda Hadid announced their separation in 2015. Prior to Hadid, Foster had been married another three times already: first to fellow musician B.J. Cook, then to Rebecca Dyer with whom he had three daughters, and then to Caitlyn Jenner ex Linda Thompson, to whom he was married for 15 years.