At what point do we just opt for a Ring Pop and pinky promise instead?View Entire Post ›
Look, I get it. When you're a big Hollywood star, it's probably hard to have a "normal" relationship. Everyone is nosy as hell, the pool of people you can relate to is small, and there are millions of eyes on you, waiting for the downfall of your relationship. So, when you meet someone who gets you, it makes sense that you want to make it official. And sometimes that doesn't work out. So, you break up. Then you do it again. Then again. And again, and again, and again, until you've purchased enough engagement rings to make Thanos jealous.
Whenever there are conversations about celebrities who have been in a ton of public relationships, people are sooo quick to bring up women like Elizabeth Taylor, Taylor Swift, and J.Lo. But nobody is ever talking about the men of Hollywood and their many, many, many relationships. So, let's talk about that, shall we? Here's just a taste of the very, very long list of men who have been engaged three or more times:
1.
Larry King: nine engagements, eight marriages, and seven wives.
The TV and radio host's first engagement was to his high school sweetheart, Freda Miller. They married in 1952, when he was 19. According to People magazine, the couples' parents allegedly had the marriage annulled because they did not approve. In 1961, he married Annette Kaye. They had one son, Larry King Jr.
Marriages number three and five were to Alene Akins, a model and Playboy bunny. Yeah, that's right. They were married twice. The first time King and Akins married was in 1961, the same year King's child with Kaye was born. The second time they wed was in 1967. Akins had a son from a previous relationship, Andy, whom King adopted. The pair also had one child together, Chaia.
Between his first and second marriage to Akins, King married Mary "Mickey" Sutphin. After Sutphin and King divorced — and Akins and King divorced for the second time — then came marriage number six with Sharon Lepore, a teacher and production assistant. They were married for seven years from 1976 to 1983.
His next wedding to Philadelphia businesswoman Julie Alexander was reportedly a "celebrity-studded" one, but, like the others, ended in divorce. Next, he and actor Deanna Lund became engaged after mere weeks of dating. For the first time, though, King's engagement did not end in marriage. They broke up before they could even make it down the aisle.
His longest and final marriage was to Shawn Southwick, a performer. They married in 1997, filed for divorce the first time in 2010, stayed together, then filed for divorce again years later, shortly before King's 2021 death.
2.
Billy Bob Thornton: Seven engagements, six marriages.
Actor, musician, and Academy Award-winning writer Billy Bob Thornton has been in several public relationships with notable Hollywood stars. And a loooot of those relationships went the distance. Well, the distance being engagements, sometimes marriage, and often divorce.
Thornton is from Arkansas, where he met his first wife, Melissa Lee Gatlin. They tied the knot in 1978, when Thornton was in his early 20s and had one daughter, Amanda Brooke Brumfield. The relationship ultimately ended with Gatlin filing for divorce in 1980, citing "incompatibility and adultery on his part" as the reason for the split.
Thornton's next two marriages were to fellow actors. First, he married Toni Lawrence in 1986. Then, in 1990, he married his One False Move costar, Cynda Williams. Both marriages were short, ending in divorce.
Pietra Dawn Cherniak, a Playboy model, and Thornton married in 1993, after meeting just the year before at a restaurant in Los Angeles, California. They had two kids, and their marriage lasted until 1997, when Cherniak filed for divorce, alleging physical and verbal abuse. She also filed a restraining order against Thornton.
Thornton's next engagement was the only one that did not end in marriage. And, it was to Academy Award-winner Laura Dern. In an interview, she said the two met at a Miramax party, and the relationship later bloomed. During their relationship, the pair starred in a movie that Thornton also wrote and directed, Daddy & Them.
Dern claims that, right in the middle of their engagement, she went out of town to work on a movie and, while gone, found out that Thornton had married someone else.
The someone else in question? Angelina Jolie. Undisputably, Thornton's whirlwind marriage to Jolie is the most notorious of his relationships. Wearing jeans, they eloped in Vegas in 2000, after (shocker) meeting on the set of Pushing Tin, which was released the year prior. At the time of their marriage, Jolie was 24, and Thornton was 44.
Seemingly every time the pair stepped out on the town, a bevy of headlines followed. They swapped underwear, which the public knew, for some reason. They had each other's names tattooed. And most notably, they each wore a necklace with the other's blood inside. #CoupleThings <3
Later, Thornton remarked that the blood necklace wasn't nearly as dramatic as people made it out to be: "The necklaces were a very simple thing: 'Hey, let's poke our fingers with a pen and smear a little blood on there, and when we're away from each other we'll wear the necklace.' It was that easy. But by the time it came out in the press, it sounded like we were wearing a bucket of blood around our necks."
While they were still together, Jolie adopted her first child as a single parent in March 2002. Though the plan was reportedly to raise Maddox together, the pair filed for divorce just four months after the adoption.
They remained on seemingly good terms following their split. Thornton spoke about Jolie in 2018, 15 years after the divorce was finalized in 2003, saying, “That was a great time. Angie is still a friend of mine, and she’s a great person, and she’s done so much."
For Thornton, the sweet spot is apparently seven engagements and six marriages, because the next time he took marriage vows was with his sixth (and current) wife, Connie Angland, a special effects artist and puppeteer. Angland's sister, a makeup artist, introduced them in 2003. In 2004, they had a daughter, Bella.
Initially, Thornton was opposed to getting married, given the press surrounding his five failed marriages thus far. But, after over 10 years together, Angland and Thornton got married in a private ceremony, which he later said was for Bella's sake. Thornton and Angland are still married.
3.
Johnny Depp: Four confirmed engagements, two marriages, and two rumored engagements.
Johnny Depp's first marriage was short-lived. Not yet an actor, the then-20-year-old was married to makeup artist Lori Anne Allison from 1983 until their separation in 1985.
Whether or not Depp's first relationship in the public eye ended in a failed engagement has been debated. He dated fellow actor Sherilyn Fenn for 2.5 years. Fenn described their relationship as "real love," and some reports even claimed that the two were engaged.
Depp's next engagement was with another big name — Jennifer Grey, who was fresh off her Dirty Dancing fame. They got engaged after dating for about two weeks. Yes, like 14 days. Like 1,2,3,4,5,6,7,8,9,10,11,12,13,14 days of dating, then they were engaged to be married for nine months.
Like the rest of their relationship, their breakup was straight out of a movie. In her book Out of the Corner, Grey wrote that she struggled with the fact that her fiancé was becoming an incredibly famous "heartthrob," and said she left him via note.
With Depp, it's hard to say which of his relationships was the most notable. However, his engagement to his Edward Scissorhands costar, Winona Ryder, is a top contender for the title, to be sure.
Ryder, who was 18 at the beginning of the relationship, and Depp, who was 27, were together for three years, and engaged for most of that time. Depp took his proclamation of love for Ryder to the extreme, getting "Winona Forever" tattooed. They broke up in 1993, ending the engagement, and years later, Depp changed his tattoo to read "Wino Forever."
Another rumored engagement for Depp was with model Kate Moss. They were together for three years, and it was seemingly a tumultuous whirlwind. Moss said the end of the relationship resulted in "years and years of crying."
During Depp's relationship with Moss, he was reportedly arrested for "smashing" furniture and glass in his hotel room. Criminal mischief felony charges were dropped after Depp paid nearly $10,000 in damages.
Depp's next relationship was his longest — he spent 14 years with model Vanessa Paradis, and the pair had two children, Lily-Rose and Jack Depp, but they were never known to be engaged or married.
Amber Heard and Johnny Depp announced their engagement in January 2014. At the time, Heard was 27, and Depp was 50. Despite his engagements that preceded it, their 2015 wedding marked Depp's second marriage.
In 2016, Heard filed a restraining order against Depp, alleging domestic abuse on multiple occasions. He denied those allegations. The couple divorced later that year, but the divorce settlement was far from the last time they'd undergo legal proceedings related to their relationship.
Two years after their 2016 divorce, Heard authored an op-ed in the Washington Post titled, "I spoke up against sexual violence — and faced our culture's wrath. That has to change." She wrote about "[becoming] a public figure representing domestic abuse." Though she did not mention Depp by name, he sued her for defamation. Then, she countersued him, also for defamation.
In the years since his divorce from Heard, Depp has seemingly not popped the question of marriage to anyone again. But, in 2024, the then-61-year-old was romantically linked to a 28-year-old model.
4.
Don Johnson: Two wives, three confirmed marriages/engagements, and two additional rumored marriages/engagements.
The Miami Vice actor's first (and second... I know, stay with me) confirmed public marriages were to the same person — actor Melanie Griffith. But before their 1976 nuptials, Don Johnson was rumored to have been married twice. The information about those two unconfirmed marriages has been kept semi-private.
Years later, after a host of prominent relationships with fellow celebrities like Barbra Streisand and model Patti D'Arbanville, with whom he shares a son, Johnson and Griffith got back together. In 1989, they married again and welcomed a daughter, actor Dakota Johnson. This marriage lasted nearly five years before the couple divorced in 1996.
In 1999, Johnson married Kelley Phleger, his current wife, whom he calls "a saint." They've been married for 27 years and have three children together.
5.
Brad Pitt: four engagements, two marriages.
But, before his marriage and subsequent divorce to Jolie, Pitt marched down the aisle once more, and almost tied the knot two additional times.
The first of Pitt's four actor fiancées was Jill Schoelen. The pair shared the screen in Cutting Class, then reportedly became engaged for only three months. According to E! News, Pitt found out that Schoelen fell in love with the director of a film she was working on in Budapest and ended the engagement.
The second of his failed engagements was with Gwyneth Paltrow. Like many of Pitt's relationships, they met on set, this time for the movie Se7en. They got engaged in Argentina, but their engagement lasted only about six months before they split up in 1997.
Then, after seven years together and five years married, they announced their separation in 2005. Jolie and Pitt officially became a couple shortly after, sparking controversy over the potential overlap of their timelines. Both Jolie and Pitt denied having a physical relationship while he was still married to Aniston, but they say they "fell in love" while filming Mr. & Mrs. Smith in 2004, when Pitt and Aniston were still married.
6.
Frank Sinatra: four marriages.
Taking it allll the way back to ol' blue eyes, Frank Sinatra was married four times. When Sinatra became a big name in the entertainment scene, he was already married to his hometown sweetheart, Nancy Barbato, and together, they had three kids.
Their 12-year marriage faced immense strain as Sinatra grew into a household name, and made tabloid headlines over his apparent affair with fellow movie star Ava Gardner, who was married to Mickey Rooney at the time. Barbato seldom did interviews, but she once commented on why she didn't immediately leave him as rumors of infidelity swirled, saying, "I have something too fine and precious to give up."
Barbato and Sinatra eventually divorced in 1951, and 72 hours after it was finalized, he and Gardner married.
The relationship of Gardner and Sinatra is one of Hollywood's messiest, most tumultuous, and infamous. They cheated on each other. Fought loudly in public. And, talked about each other in, uh, interesting ways to the press. Once, Gardner gave a very succinct reason as to why she didn't leave Sinatra, who apparently weighed 119 pounds: "Well, I'll tell you—nineteen pounds is cock."
Years after his second divorce, a 50-year-old Sinatra found his next leading lady in a 21-year-old Mia Farrow. It was short-lived, only lasting two years before Farrow was served divorce papers on the set of Rosemary's Baby. She recalled the event, saying, "He left me because I wouldn't leave the movie when he told me to leave it."
Despite the rather dramatic end of their marriage, they reportedly remained friends following their split, and even after Sinatra's 1998 death, Farrow continued to speak fondly about their friendship.
And, finally, like many others on this list, Sinatra's last marriage was his longest by far. Barbara Marx wrote in her memoir, Lady Blue Eyes: My Life With Frank, that she'd met Sinatra long before their 1976 marriage, which would last until his death.
7.
Donald Trump: three marriages.
Trump loves traditional family values so much that he's been married three times, which, apparently, makes him the only president with such a marital history. Shocker, am I right?
The next year, Trump, 47, had his fourth child, Tiffany, with Marla Maples, 29, and married two months later. His second marriage was his shortest by far, only lasting from 1993 to 1997, when they separated. A 58-year-old Trump found his final wife in Melania, who was 34 at the time of their 2005 Palm Beach, Florida wedding.
8.
Ryan Reynolds: three engagements, two marriages.
Now I'm here to remind you (or tell you for the first time) that there was once a time that Reynolds and Grammy Award-winner Alanis Morissette were engaged. Canadians in love! The Deadpool actor and Jagged Little Pill writer were together for five years and engaged for three, but never made their union legally binding.
The start of his next relationship was kept semi-private. It's unclear when Scarlett Johansson and Reynolds began their romance, but they announced their engagement in 2008, the year after Reynolds's engagement to Morissette ended. Johansson was 23 at the time, and Reynolds was 31. They married just a couple of months after the engagement, in September 2008.
They announced their separation and subsequent divorce in 2010, after two years. Neither party has commented much on their marriage. Johansson once remarked that "the logistics of being with another actor are challenging...there has to be a real understanding of how you share your time, especially when two people's careers are going at the same rate. Or even if one person is more successful than the other, that also proves challenging. There may be a competitive thing," which was believed to be a comment about her relationship with Reynolds.
He had a couple of rumored flings and relationships after his divorce with people like Sandra Bullock, his costar in The Proposal, and Charlize Theron. Then, in 2012, Reynolds got married for the second time, controversially, on a plantation, to Blake Lively, with whom he had previously shared the screen in the 2011 movie Green Lantern. Lively, 38, and Reynolds, 49, have four children.
And, finally:
9.
Tom Cruise: three marriages.
Tom Cruise (originally born Thomas Cruise Mapother IV) has been married three times, all to fellow showbiz people. After his breakup with Cher (yes, really), Cruise met actor Mimi Rogers in 1985.
Rogers was raised as a Scientologist, though she's since left the church, and is credited with introducing Cruise, one of the most famous Scientologists, to the religious group.
Their marriage was brief, ending after just three years. Rogers later said of her divorce that the disparity in their levels of fame wasn't frustrating to her so much as how often their six-year age difference was brought up. "The age thing really got on my nerves," Rogers said. "Every six months, they'd add another year. If we were still together now, I'd get 60."
Shortly after Cruise and Rogers divorced, he met Nicole Kidman, with whom he recalls feeling instant attraction. They got married on Christmas Eve in 1990 and adopted two children together in 1992 and 1995.
During their decade-long marriage, the pair starred in two movies together: Far and Away and Eyes Wide Shut. In 2001, they divorced, and the actor celebrated her ability to wear heels again.
A 42-year-old Tom Cruise met his third wife, the 26-year-old Dawson's Creek star Katie Holmes, in 2005.
When talking about his relationship with Holmes on Oprah, Cruise did something that would've given me the ick in an intergenerational way — he jumped up and down on the couch while proclaiming his excitement about their relationship. Apparently, this worked for Holmes, though, because that same year, they welcomed a daughter, Suri, whom Holmes would later gain primary custody of. They married the next year, in 2006, but Holmes ultimately would file for divorce six years later. Cruise hasn't remarried since.
WHEW, I'm tired! And, I haven't even been engaged once! Anyways, I need to lie down. In the meantime, give us all your thoughts in the comments, and let us know if we missed anyone on this list.
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