14 Celebrities Who've Been Engaged the Most Times: Danielle Staub, Elizabeth Taylor and More

Danielle Staub – 21 Engagements

Danielle Staub tops the list with 21 engagements.

Her latest was with Oliver Maier after he popped the question during a vacation to the Cheval Blanc Maison in St. Barth in 2019. However, the Real Housewives of New Jersey star might have another ring from a new man soon as the pair called off their engagement in September 2019.

Staub spoke about her relationships in a 2020 episode of RHONJ .

"Why? No one's ever asked me. It came from wanting to punish people who were abusing me," said Staub. "But, the way I got them to ask me to marry them quickly is I said I was a virgin and I would not have s-- until I was married. That will put a ring on your finger real quick. Can't do that once you have kids. If Tom [Staub] was number 19, and there were only two more after that, and I married one of them, have I really been engaged that many times? No."

Danielle only managed to make the virginity claims before giving birth to her first child.

Meanwhile, Danielle has only been married thrice to Kevin Maher , Marty Caffrey and Thomas.

Elizabeth Taylor – 10 Engagements

Elizabeth Taylor , who died in March 2011, was engaged 10 times. William Pawley Jr. became her first fiancé, followed by Conrad Hilton Jr. , who was also her first spouse and first divorce.

The eight other men include Michael Wilding , Mike Todd , Eddie Fisher , Richard Burton , John Warner , Larry Fortensky , Victor Luna and Dennis Stein .

Zsa Zsa Gabor – 9 Engagements

The second runner-up in the 1933 Miss Hungary pageant, Zsa Zsa Gabor , had nine engagements — and marriages. Her first fiancé and husband was Turkish diplomat Burhan Belge . After their divorce, Gabor moved on with Conrad Hilton .

Gabor moved on several times, marrying and divorcing George Sandards , Herbert L. Hutner , Joshua S. Corden Jr. , Jack Ryan , Michael O'Hara and Felipe de Alba .

She wed Prince Frederic von Anhalt in 1986 and stayed with him until she died in 2016.

Larry King – 8 Engagements

Larry King had eight engagements and marriages with seven women before his death on January 23, 2021.

"I think in my life I have loved three people — married all three," King told CBS News when asked about his weddings. "The other marriages I wasn't in love. It was the thing to do. I used to say, what if your wife called urgent on one line, on the other CNN called urgent … which one do you pick up? … I used to say CNN."

Larry married his high school sweetheart, Freda Miller , in 1952. After their marriage was annulled by their parents the following year, he went on to pop questions to several women, including Annette Kaye , Alene Akins , Mary Francis "Mickey" Sutphin , Sharon Lepore and Julie Alexander .

Shawn Southwick was his last wife, but he filed for divorce from her in 2019.

"We had a big age difference, and that eventually takes its toll," Larry said. "It became an issue. Also, [Shawn] is a very religious Mormon, and I'm an agnostic atheist, so that eventually causes little problems. We overcame a lot, but eventually, it became a ships-passing-in-the-night situation."

Billy Bob Thornton – 7 Engagements

Billy Bob Thornton has been married six times, though five of which — to Melissa Lee Gatlin , Toni Lawrence , Cynda Williams , Pietra Dawn Cherniak and Angelina Jolie — ended in divorce.

He was also engaged to Laura Dern before his romance with Angelina started.

After his failed relationships, Billy Bob married Conning Angland in 2014.

Gary Oldman – 6 Engagements

Five women became Gary Oldman 's fiancées before he married his current wife, Gisele Schmidt . He was engaged to singer Alexandra Edenborough and shared a seven-year marriage with her before moving on with Donya Fiorentino , Uma Thurman and Lesley Manville in the years thereafter.

Gary was also previously engaged to actress Isabella Rossellini , though their relationship did not progress from there.

Jennifer Lopez – 6 Engagements

Jennifer Lopez also went through failed engagements and marriages before returning to her now-husband, Ben Affleck .

She initially got engaged and married to Ojani Noa before doing the same with Cris Judd . After her first two marriages, Lopez met Affleck and got engaged to him in 2003, only to call things off the following year.

The singer married Marc Anthony but divorced him in 2011 — before moving on with Alex Rodriguez .

In April 2021, the star and the baseball player broke up amid rumors she went back to Affleck. The former exes officially rekindled their relationship and finally got married decades after their first engagement failed.

Johnny Depp – 6 Engagements

Johnny Depp was engaged and married to Amber Heard and Lori Anne Allison . He also proposed to Winona Ryder , Jennifer Grey and Sherilyn Fenn .

Some reports claimed that he was also engaged to Vanessa Paradis , but neither confirmed it.

David Foster – 5 Engagements

David Foster has been engaged and married four times to B.J. Cook , Rebecca Dyer , Linda Thompson and Yolanda Hadid .

In 2018, David proposed to his current wife, Katharine McPhee , and tied the knot with her in London in June 2019.

Drew Barrymore – 5 Engagements

Drew Barrymore has been married thrice but engaged five times. Her first was with Leland Hayward when she was 16 before her engagement to Jamie Walters .

Her other fiancés include Jeremy Thomas , Tom Green and Will Kopelman .

Jodie Sweetin – 5 Engagements

Before Jodie Sweetin married her husband, Mescal Wasilewski , she wed four other men, starting with Shaun Holguin . She was also with Cody Herpin , Morty Coyle and Justin Hodak .

Kelsey Grammer – 5 Engagements

Kelsey Grammer has been engaged five times, and four of those led to marriages.

The Fraiser actor's first wife was Doreen Alderman . After their eight-year marriage ended in the 1990s, Kelsey gave Leigh-Anne Csuhany a ring and tied the knot with her in 1992.

Following their split, he moved on with Tammi Alexander — though they never walked down the aisle.

Kelsey then wed Camille Donatacci , though their relationship lasted only 13 years.

He is now with his fourth and current wife, Kayte Walsh .

Lisa Marie Presley – 5 Engagements

Lisa Marie Presley was engaged five times, first with Danny Keough before her marriage to Michael Jackson . She was briefly engaged to John Oszajca before Nicolas Cage came into her life.

Lisa Marie's last husband was Michael Lockwood , from whom she filed for divorce in 2016.

Marc Anthony – 5 Engagements

Marc Anthony popped the question to four women before his marriage to Nadia Ferreira in 2023.

His first engagement was with Claudette Lali , but they broke up in 1998. The "Tu Amor Me Hace Bien" singer was also engaged and married to Dayanara Torres , Lopez and Shannon De Lima before his romance with Ferreira started.