It’s got to be hard to be in a love triangle with your best friend, and it's even worse when you’re all very famous. But that is exactly what happened in the late 1950s with the amazing Elizabeth Taylor and Debbie Reynolds. Theirs is a story of woe, as Debbie was married to Eddie Fisher (Carrie Fisher’s Dad). However, lo and behold, after the death of Liz’s 3rd husband, Mike Todd, Eddie rushed to Taylor’s side to comfort her at the behest of Debbie. That’s when the unthinkable happened--Eddie fell for the violet-eyed Liz and divorced Debbie to become Liz’ 4th husband.
That marriage lasted five years. When she co-starred in Cleopatra with Richard Burton, the two began a scandalous affair that led to the Fisher/Taylor dissolution, so that the Taylor/Burton union could begin. Richard and Liz eventually married in 1964, divorced 10 years later, and then remarried in 1975.
These two lovebirds kept their love affair a secret for over two decades. They met during the filming of Woman of the Year, where sparks flew. While people flocked to their films to enjoy the witty banter and undeniable chemistry, the pair never went public.
Tracy was a devout catholic, so divorce was not an option. In order to see Hepburn, he would live much of his life in hotels and rented residences separate from his married life. Even at the end of his life, Katharine took time off from her schedule to care for him, and she was by his side when he died in 1967. Out of respect for the family, Hepburn didn’t attend his funeral, nor did she speak publicly of their relationship until Spencer’s wife died in 1983.
She was a Jewish girl from the Bronx, and he was an Episcopalian from Manhattan. However, their May-December romance had scandal, nonetheless. Humphrey Bogart was 45 when he met 19-year-old Lauren Bacall on the set of To Have And Have Not. Humphrey had been married thrice and was still married to Mayo Methot at the time.
He quickly divorced her in January 1945 and married his love Bacall in May 1945. The couple had two children together and remained together until Humphrey’s death in 1957. "No one has ever written a romance better than we lived," she wrote in her memoir. After her death on Aug. 12, 2014, she was interred at Forest Lawn Memorial Park in Glendale, California, the same cemetery as Bogart.
Frank Sinatra was something of a ladies’ man and was linked to almost a dozen famous ladies in his lifetime. Sinatra began dating actress Ava Gardner, while still married to his wife Nancy with whom he shared three children. He eventually left Nancy for Gardner, whom he married in 1951.
Theirs was a turbulent marriage and Gardner filed for divorce in 1954. Sinatra blamed Peter Lawford for the split. However, he continued to manage Ava’s business affairs. Fast forward to 1966 and Sinatra married Mia Farrow, who was 21 to his 50. Again, another tumultuous marriage began, and Sinatra served her with divorce papers on the set of Rosemary’s Baby.
Before Princess Diana, there was Camilla Shand. And if you know anything about the Royal Family or watched The Crown, you know how it all went down. Prince Charles and Camilla met at a polo match in 1970 and dated for less than a year. After remaining friends, the two started an affair while they were both in high-profile relationships up until and through their respective marriages.
Naturally, you’ll remember that Charles wed Diana in 1983 after Camilla wed Andrew Parker-Bowles. In an interview, Charles admitted to adultery, but said he fought for his marriage “until it became clear that the marriage had irretrievably broken down.” When Charles and Diana divorced, it was assumed that Charles and Camilla would wed--although that didn’t happen until later after Diana’s unfortunate death. Because of the Church of England’s stance on divorce, Prince Charles and Camilla were married in a civil ceremony in England.
In the game of love, Blake Shelton took a minute to get there. Shelton was married to Kaynette Williams when he discovered he was head over heels in love with Miranda Lambert with one look. Miranda knew he was off the market, but that didn’t stop her from pursuing Shelton. Lambert said, “I've seen this my whole life—affairs, and of all people to know better, I know better than this.”
The couple wed in 2011 and divorced in 2015. However, we’re just getting started--because Blake soon turned an eye toward his The Voice co-star, Gwen Stefani, who was in the midst of her 20-year relationship fallout with Gavin Rossdale. The couple (Blake and Gwen) are currently engaged for their nuptials.
Golden couple Paul Newman and Joanne Woodward were considered relationship goals in Hollywood. But the truth is that Newman was married to Jackie Witte when they met and started their torrid affair on the set of The Long, Hot Summer in 1957.
Newman’s wife agreed to a divorce in 1958. Almost immediately after, Paul married Joanne Woodward in Las Vegas. Woodward stepped back from the camera to focus on their married life and three daughters. The duo celebrated their 50th wedding anniversary in 2008 shortly before Paul’s death from lung cancer.
Angelina Jolie was married to Johnny Lee Miller until their split in 1999. She married now ex-husband Billy Bob Thornton after meeting him on the set of the 1999 movie Pushing Tin. They married that same year. The only problem was that Billy was engaged to actress Laura Dern. “I left our home to work on a movie, and while I was away, my boyfriend got married and I’ve never heard from him again,” Dern said at the time.
Angelina and Billy divorced in 2003. However, history kind of repeated itself again when Angelina connected with co-star Brad Pitt on the film Mr. & Mrs. Smith, but Brad was married to Jennifer Aniston at the time. After a divorce, Pitt and Jolie settled down with multiple kids--both adopted and biological. Unfortunately, Jolie filed for divorce in 2019.
What became known as the most iconic love story in country music started with infidelity. The “Walk The Line” singer was married to Vivian Liberto when he started his affair with June Carter. She was married to honky-tonk singer Carl Smith at the time. The two met on the stage of the Grand Ole Opry and history was rewritten.
They started touring together, and Carter divorced Smith, but then married a police officer named Edwin Nix. Johnny’s wife divorced him in 1967. Cash continued to struggle with addiction issues and June stepped in to help him kick his demons. They wed in 1968 and remained married until her death in 2003.
Director Woody Allen was in a long-term relationship with Mia Farrow and had been since 1979. Mia had previously been married twice--once to Frank Sinatra and again to Andre Previn. It was during her relationship with Previn that she met Allen. Their relationship went along for 13 years and through several adopted children.
Allen was 56 when he started a relationship with Soon-Yi Previn, the 21-year-old adopted daughter of Mia and Andre. The relationship exploded and caused issues for everyone involved. Allen and Previn married in 1997 and remain married today as the parents of two adopted daughters.
Jennifer Lopez was married to backup dancer Cris Judd when she met Ben Affleck. Judd and Lopez divorced in 2002, and JLo got engaged to Affleck in November 2002. However, cold feet led to them calling off the wedding before walking down the aisle.
She began seeing Marc Anthony in 2004 and tied the knot with him just four days after his divorce from Dayanara Torres was finalized. After being a couple for 10 years, JLo and Marc divorced. Fast forward a few years to February 2017, where JLo started dating Yankee superstar Alex Rodriguez. They planned to marry until April 2021 when, you guessed it, rumors of an affair (Madison LeCroy) on the part of A-Rod derailed the relationship.
Kim Kardashian married NBA star Kris Humphries in May 2011. After 72 days of marriage, Kim filed from divorce. However, the NBA star was quick to say Kim cheated on him in 2012 with Kanye West, while still legally married.
Kim claims she only dated Kanye after her separation from Humphries. The two got engaged on October 21, 2013 and married in 2014. Kim and Kanye have four children together, a historic blizzard of celebrity, and numerous awards. However, citing irreconcilable differences in February 2021, Kardashian and West filed for divorce and agreed on shared joint custody.
This "staunch" Republican from New York also became the 45th President of the United States. However, family values aside, The Don, while married to his first wife, Ivana, proceeded to have a torrid affair with actress Marla Maples in 1989. The affair blew up in the tabloids, especially after Marla found out she was pregnant in 1992, at which point Ivana divorced him.
Maples and Trump welcomed their daughter Tiffany in 1993, and the couple married a few months later. They divorced in 1999. In 2005, Trump married Melania Knauss with whom he had a son, Barron.
Country singer LeAnn Rimes and CSI: Miami star Eddie Cibrian met on the set of the 2008 Lifetime movie Northern Lights. Rimes was married to former dancer and chef Dean Sheremet, and Eddie was betrothed to Real Housewives of Beverly Hills star Brandi Glanville
But love was not to be discouraged between these two, and Rimes divorced Sheremet while Cibrian dumped Glanville. Despite being the center of one of the biggest controversies in the first half of the decade, the two now live as a relatively normal couple—and Rimes doesn’t regret the way things turned out.
'90s darling Meg Ryan married Dennis Quaid in 1991, and then they had a son, Jack. However, Meg met Russell Crowe on the set of the 2000 thriller Proof of Life, and the pair had undeniable chemistry.
When her affair with Russell Crowe became public, it ended her marriage to Quaid in 2001. However, the relationship was moving too fast for Meg, who had left the relationship by Christmas 2001. Meg states: “I remember letting go of needing to correct anybody. Divorce is hard. Love is hard. All those things were so personal. They weren’t for mass consumption.”
Alicia Keys and Swizz Beatz had known each other since they were teenagers, but at first, Keys wanted nothing to do with him, saying, “Honestly, I didn't really like him that much. I thought he was too ostentatious. Everything with him is really over the top.” However, that all changed when they started working professionally together.
The two had a connection, which was great but unfortunately, Swizz Beatz was still married to another singer, Mashonda. That definitely didn’t help their relationship any and the ensuing divorce was very public and very messy. However, things eventually died down, and Keys and Beatz are still together and now have two kids.
Both Tori Spelling and Dean McDermott were already in relationships when they first met on the set of the 2005 Lifetime movie Mind Over Murder. However, that didn’t stop them from having an affair with one another. In fact, Spelling later revealed that she and McDermott slept with each other on the first night they met.
Both Spelling and McDermott would go on to divorce their respective spouses and marry less than a year after the separations. However, it wasn’t all smooth sailing for the couple after that. In 2013 it was revealed that McDermott had actually cheated on Spelling during their relationship. The two managed to stay together, but their relationship hasn’t been the same ever since.
As strange as it sounds, ‘90s NBC sitcom Fraiser and The Real Housewives of Beverly Hills have a special connection to one another. It turns out that actor and Fraiser star Kelsey Grammer is actually married to a RHOBH housewife--Kayte Walsh, to be specific. However, this budding relationship actually destroyed another one.
When Grammer and Walsh first began dating, he was actually still married to Camille Grammer at the time and had been for thirteen years. For better or worse, the ensuing divorce drama was available for the public to see on episode after episode of RHOBH. After things had died down, Walsh said in an interview that she was “not proud” of how her relationship to Grammer got started.
Britney Spears and Kevin Federline's marriage was a huge deal at the time. Britney Spears was one of the biggest, most talented pop stars of the time and Kevin Federline was…well, nobody knows to this day just what he was or what she saw in him. But looking back now, perhaps it was a desperate cry for help.
Whatever she happened to see in him, Federline was actually engaged to another woman at the time that he and Spears first met. In fact, the other woman, Shar Jackson, was actually pregnant with Federline’s second child at the time. And his relationship with Spears didn’t fare any better--their marriage only lasted two years.
Ultimately, no one ends up looking that good when they’re part of an affair. But in the case of actors Claire Danes and Billy Crudup, he ends up looking like way more of a jerk than she does. And that’s because he left his then-wife fellow actor Mary-Louise Parker to be with Danes. Oh, and did we mention that she was pregnant at the time that he left? Not great.
And despite all the trouble that the two went to to be in a relationship, things didn’t end up working out for Danes and Crudup. The two were only together for four years before they ended things. Later, Danes said this about the relationship--”I was just in love with him and needed to explore that, and I was 24… I didn’t quite know what those consequences would be.”
Country star Jason Aldean began his 12-year marriage to Jessica Ussery in 2001, fathering two daughters during that time. But when he walked out on Ussery in 2012 for American Idol contestant Brittany Kerr, his entire life changed. "The truth is that I screwed up,” Aldean apologized. “I really appreciate being able to work through this privately with my family and for all your continued support.”
Despite the highly questionable way their relationship began, Jason Aldean and Brittany Kerr have strangely made it all work. After a short dating period, the two finally tied the knot in 2015. And these days, the two are busy raising their young children together--a son and a daughter.
These days, celebrities cheat on each other all the time, it seems like. Someone’s always in the midst of some sort of relationship drama that eventually fizzles out and is forgotten. But that wasn’t the case back when Ingrid Bergman was one of Hollywood’s biggest names. In fact, her affair ruined her career entirely.
Bergman met Italian director Roberto Rossellini when the two were both working on the 1950 film Stromboli. The two began a relationship, which was eventually exposed publicly, while Bergman was still married to a dentist. Unfortunately, Rossellini would go on to cheat on Bergman, and they ended up divorced as well.
Acting duo Jack Nicholson and Anjelica Huston’s 17-year relationship ended nastily when Nicholson admitted he was fathering a child with Rebecca Broussard.Nicholson said their breakup was “quite a quandary” during an interview with Parade. “I immediately told her what was up, and she made the decision for us. Anjelica’s first response was, ‘You have to support this woman,’ Her second response was to come down to my job and beat the hell out of me. She really beat me up, I tell you.”
He might have taken a beating from Anjelica Huston to be with this new woman, but that didn’t mean his new relationship was meant to last. Nicholson and Broussard ended up having a couple of kids together, but they eventually called the relationship quits in 1994. It doesn’t quite seem worth it, in retrospect.
Nothing about the relationship between Mel Gibson and Russian musician Oksana Grigorieva was very wholesome--including how it got started. Shortly after Gibson’s former wife filed for divorce, it was made public that Gibson was expecting a child with Grigorieva, whom he had been having an affair with.
Things would only go from bad to worse in this relationship, though. The two were only together for about three years, and their relationship would end after allegations of physical abuse against Gibson and a messy custody battle. Gibson agreed to settle the domestic abuse case for $15 million, but Grigorieva eventually dropped her claims.
Antonio Banderas has no trouble attracting women, but it seems he might have a little difficulty keeping track of who he’s in a relationship with. From 1988 until 1996 he was married to Ana Leza. However, the end of this relationship overlaps with the beginning of his next one.
Banderas met Melanie Griffith on the set of the 1995 rom-com Two Much, and the two quickly began a relationship. It’s believed that this was the cause for the divorce from his first wife. Banderas and Griffith tied the knot in 1996 and seemed like a happy couple. However, they announced their split in 2014.
Ryan Phillippe and Reese Witherspoon married young in the 1990s after meeting at her 21st birthday party. The two had a couple of children together, but, in 2006, Witherspoon wanted out of the relationship and filed for divorce. But just what spurred her on?
While nothing has been made public, it’s been rumored that the pair split because Philippe was having an affair with Australian actress Abbie Cornish. The two began publicly dating in 2007, which was a full year before his divorce from Witherspoon was finalized. However, we may never know for sure unless someone spills the beans.
Sometimes art imitates life--or maybe life imitates art? In the case of Debra Messing and Will Chase, things get a little murky. At the time they began their relationship, both were on the musical drama TV show Smash, where their characters were having an affair. However, they were dating off screen as well.
The only problem was that the beginning of this relationship seems to have a bit of overlap with her divorce from actor Daniel Zelman, whom she had been married to for eleven years. Things may have been over between the unhappy couple before she began dating Chase, but we can’t imagine that made the divorce any less dramatic.
It’s not clear whether Jennifer Aniston and Justin Theroux started out as an affair, but the beginnings of their relationship throw up a lot of red flags. The two met on the set of the 2012 comedy Wanderlust and began dating suspiciously quickly after Theroux divorced his first wife Heidi Bivens.
That’s not damning evidence in and of itself, but their story sounds a whole lot like some of the others we’ve seen on this list. Despite the questionable beginnings of their relationship, the two eventually married in 2015. However, by 2018 they had called it quits and divorced.
There has never been any direct, public evidence that the relationship between Ethan Hawke and Ryan Shawhughes began as an affair. But let’s just say that the circumstances surrounding how this couple met is more than a little suspicious. You see, Shawhughes was the nanny for Hawke and his then-wife Uma Thurman. What a coincidence he starts up a relationship with her right after his divorce.
That being said, the two still seem to be a happy couple with two children. However, Hawke has said some things that have made people question the fidelity in this relationship too, like, “My relationship with my present wife is thrilling to me and I'm committed to it. But neither she nor I know what shape the future will come in. Sexual fidelity can't be the whole thing you hang your relationship on.”
Megan Fox and Machine Gun Kelly are another relationship that has no direct proof of starting as an affair. All we know is that the two Hollywood stars were spending a lot of time together before they went public (and before Fox was divorced from her former husband).
Fox was formerly married to fellow actor Brian Austin Green for ten years before divorcing him in 2020. Since her new relationship with Machine Gun Kelly, Green has been throwing some hilarious shade at the couple on social media, which only helps to fan the rumor flames surrounding their recent breakup.
