For people of a certain age, Michelle Williams will always be best known for her portrayal of Jen on Dawson's Creek. However, she's done just fine for herself in the world of acting since the 1990s with numerous other hits—but when it comes to love? Things are a little messier for Williams in this area of life.
In addition to being attached to Heath Ledger for a time, Williams tied the knot with Phil Elverum in 2018. Things didn't work out for the couple, and they announced their split in early 2019. The only problem? Williams became involved with director Thomas Kail in late 2018 before she had actually split from Elverum! Despite this, Williams and Kail have been together ever since.
These days, musician Bruce Springsteen and his wife (and fellow musician) Patti Scialfa seem like a pretty normal married couple—they've been together for more than 30 years, after all! However, the origins of this relationship are a bit messier than some fans of The Boss might realize!
In the late '80s, Springsteen married Julianne Phillips, but there was only one problem—according to his memoir, after tying the knot, Springsteen realized he was actually in love with his bandmate, Scialfa. Despite divorcing Phillips in 1989, Springsteen began his relationship with Scialfa before his divorce was finalized.
A professional athlete with a messy romantic life? Color us utterly surprised. Former NBA star Dewayne Wade married his high school sweetheart, Siohvaughn Funches, in 2002, but there was trouble on the horizon for the couple. The two would eventually get divorced in 2010, and he would start dating actress Gabrielle Union. There was only one problem—the dates didn't add up!
Wade began his relationship with Union in 2008, a full two years before his divorce. The proceedings were incredibly messy, and Funches even attempted to sue Union for breaking up her marriage, although that lawsuit eventually fell through. However, Wade and Union have been together ever since, and they have one child together.
Blake Shelton and Gwen Stefani might look like a cute celebrity couple, but the origins of their relationship are incredibly scummy, and we're honestly a little perplexed as to how they trust one another to be faithful. This wasn't just an issue of having a mistress—both of them were still in relationships when they got together!
Before getting together with Shelton, Stefani was married to singer Gavin Rossdale, and Shelton was married to fellow country musician Miranda Lambert. That all changed in 2015 when Stefani and Shelton were judges on The Voice, where they developed a romantic relationship...all before actually divorcing the people they were married to!
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Actor Brad Pitt and his ex-wife Jennifer Aniston made such a great celebrity couple that people even gave them one of those obnoxious portmanteau couple's names—"Bennifer." However, there was trouble in paradise for the famous couple once Pitt met Angelina Jolie on the set of Mr. and Mrs. Smith.
While Brad Pitt and Angelina Jolie didn't go public with their relationship until his divorce from Aniston was finalized, most people assume that things started getting hot and heavy before the two had split, considering the two announcements came so close together. While Pitt and Jolie made it work for several years, they announced their own split in 2016.
Actors meeting and falling in love while filming a movie is a tale as old as Hollywood itself. Unfortunately, in a lot of these instances, the lovebirds are already "happily" married. And that's exactly what happened when Antonio Banderas and Melanie Griffith met on the set of Two Much in 1995.
At the time, Griffith was married to actor Don Johnson while Banderas was married to Ana Leza. We're sure it's not a coincidence that both couples just happened to divorce in 1996! Griffith and Banderas would stay married for more than 20 years before splitting up in 2016.
Once again, we have another Hollywood couple who fell in love while attached to other people. At the time they met, Rebecca Romijn was married to John Stamos, while Jerry O'Connell was dating Giuliana Rancic. Despite the fact that they got together a year before Romijn's divorce was finalized, they insist there was no funny business.
According to O'Connell there were no "shenanigans" despite the way things looked. He told People magazine, "Obviously, she was married, and I know shenanigans go on, but no shenanigans happened. But we clicked. Day one, we clicked." Regardless of how their relationship started, this couple has managed to make things last over the years.
While Jennifer Lopez may have had a very public romantic life, she hasn't had the most luck in the love department. Back in the 2000s, it seemed like she had found the one in fellow musician Marc Anthony, but looking back on it, we're not entirely sure why we thought this couple would work, considering they were plagued by infidelity.
While Lopez herself was not attached to anyone at the time, Anthony was still married to Dayanara Torres when they allegedly began seeing each other, and it really didn't help things that the couple got married almost immediately after Anthony got divorced. Their own relationship would come to an end in 2014.
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Of all the people in Hollywood, we would have never expected that Claire Danes would end up as "the other woman", but that's exactly what happened in 2003 when she met Billy Crudup on the set of Stage Beauty. While not married at the time, Crudup was already in a relationship with actress Mary-Louise Parker since 1996. But that's not the worst part!
What made this infidelity truly shocking and highly publicized was the fact that Parker was pregnant with Crudup's child at the time he left her for Danes. We can't imagine the relationship ended up being worth all that trouble, as Danes and Crudup had split up by 2006.
The relationship between Britney Spears and Kevin Federline was just an absolute mess for everyone involved—particularly for the woman he was dating at the time they got together! Federline was a backup dancer for Spears in the early 2000s, and the two had an immediate connection and began a relationship quickly.
There was only one problem with this whirlwind romance—Federline was already engaged to a woman with whom he had two children! That didn't seem to phase Federline and Spears, as they eventually married. However, their own relationship got ugly quickly when they divorced and fought over their kids in 2007.
It's kind of unbelievable that infidelity can lead to a happy, lasting marriage, but it happens more often than you might realize in Hollywood! One example of a strong relationship with questionable origins is between fellow musicians Swizz Beats and Alicia Keys. They began officially dating in 2010, but you know that there's more to the story than this!
While the couple didn't make their relationship official until Beats' divorce from his first wife, Mashonda Tifrere, insiders claim that the new couple was together long before this divorce became official. Regardless of the circumstances, Beats and Keys have been together ever since and have several children together.
Musician LeAnne Rimes and actor Eddie Cibrian may have been married to other people at the time they met, but that didn't stop them from pursuing a relationship. The couple first met in 2009 while filming a Lifetime movie (how appropriate), but Cibrian was married to Brandi Glanville, while Rimes was married to Dean Sheremet.
But that all changed very quickly! Within less than a year, both original couples were divorced, and Rimes and Cibrian were married. They attempted an ill-fated reality show about their new relationship, but that was mercifully canceled after one season. Regardless, the two have been married since 2011.
You might not recognize the name Jessica Sklar, but you probably are familiar with Jerry Seinfeld's long-time wife, who took his name when they married in 1999. While all that may sound perfectly normal, the way they got together was anything but! The two first met at a sports club and quickly fell in love, but there was a problem—Jessica was already married.
And when we say "already married," we're talking fresh-off-her-honeymoon married. She tied the knot with Eric Nederlander in 1998, and, unsurprisingly, their relationship didn't last a year. By the end of 1999, she was married to Seinfeld, and the rest is history. Who would have thought that America's funnyman was also the other woman?
Is this a real case of infidelity? You'll have to be the judge of that, but, like all these other relationships, the circumstances seem mighty suspicious! In 2000, actress Julia Roberts was filming The Mexican when she met cameraman Danny Moder. The two had immediate chemistry, but, at the time, Yoder was married, and Roberts was in a serious relationship.
While they eventually ended their other relationships to marry in 2002, Roberts insists that everything was above board, telling Oprah, "He sorted his whole thing out, separate and apart from me. And I sorted my life out, separate and apart from him. I think that's the only reason we were able to ultimately fall in love with each other and be together."
Tom Brady may not have actually done anything wrong when he began dating model Gisele Bundchen, but the timing of this relationship (and the end of his other) seems highly suspicious. Before getting into a relationship with Bundchen, Brady was dating actress Bridget Moynahan, and she was actually pregnant with his child when he left her for Bundchen.
While there's no public evidence that he actually cheated on Moynahan, it's definitely a scummy move to ditch your woman for someone else when she's pregnant with your child! Brady and Bundchen would eventually get married in 2009, but the couple ended up calling it quits with a divorce in 2022.
Ethan Hawke had met his current wife Ryan Shawhughes, while she was employed as a nanny for him and Uma Thurman. Hawke and Thurman had been married since 1998, after meeting on the set of Gattaca back in 1996. They had two children together, but the marriage would not last due to Hawke’s alleged infidelity.
Hawke and Thurman separated in 2003 and divorced in 2005. By 2008, Hawke married his former nanny, Ryan Shawhughes. While Hawke claims that Ryan Shawnhughes had nothing to do with the ending of his first marriage, only he and Shawnhughes know the whole truth.
Charles was famously married to Diana in the ‘80s but it was clearly not a marriage of love as Charles was said to be carrying on an affair with Camilla Parker Bowles by the mid ‘80s. The two had known each other since the mid ‘70s but their relationship had been put on hold when he met Diana.
Upon his divorce from Diana, Charles had maintained that his relationship with Camilla was non-negotiable. Despite backlash from Diana supporters, Camilla and Charles carried on their relationship and married in 2005. Camilla would become Duchess of Cornwall and later Queen consort upon Charles’s ascension to the throne.
Kelsey Grammer was married to reality TV star Camille Donatacci of The Real Housewives of Beverly Hills when he met British flight attendant Kayte Walsh. The very same year he announced his divorce in 2010, he also announced that Walsh would be having his child. However, the pregnancy ended in a miscarriage.
By December 2010, Walsh and Grammar announced they were engaged. In February 2011, they married at the Plaza Hotel in New York City. They now have a daughter and two sons, with the most recent having been born in November 2016. The couple seems to be getting on well, so hopefully, this time Grammer can keep to his vows.
Tori Spelling and Dean McDermott were both married when they met in 2005 while filming the Lifetime made-for-TV-movie Mind Over Murder. The two had an affair the very same night they met. At the time, McDermott was married to Mary Jo Eustace and Spelling to Charlie Shanian.
Shanian cited irreconcilable differences when he filed for divorce, which was finalized in April 2006. McDermott, who also divorced that year, married Spelling in May 2006. While the couple is still married, as of 2022 there are amidst a trial separation. They share five children together.
Johnny Depp wasn’t married but had been in a long-term relationship with Vanessa Paradis when he met Amber Heard on the set of The Rum Diary. The couple had two children together, including daughter Lily-Rose. His relationship with Paradis ended just as soon as his relationship with Heard began.
Of course, the marriage was ultimately doomed, becoming one of the biggest fiascos in recent memory. Depp and Heard divorced in 2017 after getting married in 2015. But it didn’t end there. Claims of abuse came from both sides, and in 2019, Depp sued for defamation and won.
Humphrey Bogart had been married to Mayo Methot until 1938 to 1945 when they divorced. That very same year, he got remarried to Lauren Bacall, making it likely they knew each other when he was still married to Methot. Nevertheless, Bogart and Bacall’s marriage would last until his death in 1957.
The two had met on the set of To Have and Have Not in 1944. They had one child together, a son named Stephen Humphrey Bogart. After Bogart’s death, Bacall had a relationship with Frank Sinatra and several other failed relationships including her second marriage to Jason Robards.
Country music singer Blake Shelton famously married Miranda Lambert in 2011. But many may not remember that he began dating her, while he was married to Kaynette Gern. Shelton and Lambert met during the CMT's 100 Greatest Duets Concert in 2005 and they dated for over four years before he proposed to her.
Shelton and Lamberts relationship was, too, doomed to fail. The couple announced their divorced in 2015. That same year, he announced a relationship with Gwen Stefani, who was also going through a divorce at the time. They ended up marrying each other in 2021.
Paul Newman was married to Jackie Witte from 1949 to 1958. They had a son together and two daughters. During this time, in 1953, it was clear from the start that he and the other woman, Joanne Woodward, had some real chemistry. As an understudy for Picnic on Broadway, Woodward caught Newman’s wandering eye.
After carrying on an affair with Woodward, he finally filed for divorce in 1957 – after filming The Long, Hot Summer. Joanne Woodward and Paul Newman remained married until his death in 2008. They had three daughters together, and Newman was said to have never had an affair during their marriage.
If you’ve seen the 2005 film Walk the Line then you are already aware of the affair and marriage between Johnny Cash and June Carter. But if you haven’t, we’ll break it down for you. Johnny Cash was married to Vivian Liberto with whom he had four children.
But as he rose to fame, he developed a close relationship with singer June Carter. Carter herself, was also married when they met. After they both divorced their spouses in 1966, Johnny Cash and June Carter became official, and married in 1968. Despite its rocky start, their love story is one of the greatest in Country music history.
Kim Kardashian’s marriage to Kris Humphries wasn’t long, but she already began dating Kanye West in 2012, while she was still legally married. Once the divorce was finalized in 2013, Kanye and Kim got engaged in 2013 and married in 2014. The high-profile marriage would last for 7 years.
In 2021, Kim filed for divorce. They agreed to end their marriage due to irreconcilable differences and agreed to joint custody. The divorced was not finalized until 2022. During the divorce, Kim Kardashian began dating Pete Davidson but that relationship ended before the divorce was even finalized in November.
Eddie Fisher was married to actress Debbie Reynolds when he began an affair with Elizabeth Taylor. To make matter worse, Debbie Reynolds and Elizabeth Taylor were friends at the time – but apparently not great friends. Taylor had been recovering from the death of her husband Mike Todd and sought comfort in the arms of Eddie Fisher.
The highly publicized affair led to the cancellation of his self-titled television show, The Eddie Fisher Show. After divorcing Debbie Reynolds, Fisher married Elizabeth Taylor in 1959. By 1962, she began an affair with actor Richard Burton – another married man. Taylor and Fisher divorced in 1964.
