Nowhere do relationships and marriages dissolve as quickly as they started more than in Hollywood. One day, a couple is being snapped kissing and canoodling by the paparazzi. The following week, the supposed couple is no longer together and one of them is cozying up to a completely different person. Long-lasting marriages, too, are a rarity and divorce rates are sky high. There are a lot of external factors to relationships being short-lived in the entertainment industry. The most common reason is conflicting and demanding work schedules, especially if they are both fan favorites. That means they are bombarded with projects, leaving them no time for quality relationships.
Sure, there are the few lucky ones who are able to make it work, but for those who have to get over failed relationships under the spotlight, it can be tough, especially if the break up was bitter. And it’s more complicated still if there are children involved. But for the sake of being able to survive harmoniously in the same industry, being civil is a must. Still, it doesn’t mean running into your ex or being forced to spend time with them is the most pleasant experience.
15 Jennifer Lopez and Puff Daddy
Jennifer Lopez has been in the business for quite a while. From being a back up dancer of Janet Jackson to a Fly Girl dancer on In Living Color, to a lucrative singing and acting career, and finally to business ventures and producing, it’s no wonder that her net worth is estimated at around $300 million. Being in the spotlight for that long has also meant being front and center when it comes to her personal life. It doesn’t help that most of her relationships have been with equally famous men, one of them being rapper Sean Combs, otherwise known as Puff Daddy and later, P-Diddy. They split in 2001, but it’s more than a decade later, she ran into him with her then boyfriend Casper Smart. Diddy looked bemused as he stuck out his hand to shake Smart’s, as Lopez looked on from between the two men.
14 Bruce Willis and Demi Moore
They were considered one of Hollywood’s golden couples at the time they were together because their marriage seemed so solid. Many were caught unawares when news broke that Bruce Willis and Demi Moore had split after 11 years together and three daughters together. But they seem to have separated on good terms as they remained close throughout the years. In fact, some people found it odd the way Willis was so close to Moore’s then boyfriend Ashton Kutcher. In fact, the former couple and their children were photographed hanging out with Kutcher. In fact, the three adults even vacationed together at Willis’ home in Turks and Caicos. And when Moore and Kutcher tied the knot, Willis was one of the guests. And when Willis married current wife Emma Heming, Moore and Kutcher were in attendance as well.
13 Simon Cowell, Sinitta, and Jackie St. Clair
Simon Cowell has been known as the notorious bachelor among his colleagues in the entertainment industry, taking the title from George Clooney when the latter fell in love and married lawyer Amal Clooney. The English reality TV judge and producer is most known for his acerbic tongue as a judge in the reality competition TV shows, Pop Idol, The X Factor, and American Idol. At 57, he has never married, but has had a string of girlfriends, including Lauren Silverman, his current partner and mother of his only child. But before Silverman, he dated British-American singer Sinitta and former model Jackie St. Clair, both of whom he posed with on the red carpet of the 2010 National Television Awards in London. All three seemed to take it in stride, but it made for an awkward photo nonetheless, with Cowell being flanked by both of his exes.
12 Jennifer Lopez and Casper Smart
She has dated many men in her time as a celebrity and the paparazzi makes sure to document each and every relationship almost every step of the way. Jennifer Lopez has had a string of men on her arm. She’s been married three times. Her first husband was to Cuban waiter Ojani Noa, whom she was embroiled in a legal battle with regarding him publishing a book about their marriage. She married her former back-up dancer Cris Judd, but the marriage was also short-lived, lasting less than a year. Her third husband was long-time friend Marc Anthony, by whom she has twins. When her third marriage ended, Lopez started dating another former back-up dancer, Casper Smart, but they officially ended things on August 2016. While she was out with good friend Leah Remini in Los Angeles, she bumped into Smart, who was carrying a bouquet of flowers. It’s not certain who those flowers were for, but the conversation seemed amicable enough.
11 Reese Witherspoon and Ryan Phillippe
Those who are fans of Reese Witherspoon and or Ryan Phillippe would know that the former couple fell in love while filming the 1999 cult drama film Cruel Intentions. They married and had two children, Ava and Deacon, and throughout the marriage, Witherspoon’s career continued to soar. She appeared in the highly successful films, Sweet Home Alabama, Legally Blonde, and its sequel, before gaining serious actress status in the film Walk The Line, for which she received an Academy Award for Best Actress. It’s unclear why the couple split, but despite the fact that they have since moved on, they have tried to maintain a civil relationship for the sake of the children. Back in 2013, the ex-couple watched their sons’ soccer game, accompanied by Witherspoon’s current husband, Jim Toth and a lady friend of Phillippe’s.
10 Britney Spears and Kevin Federline
The small-town Mississippi girl who joined the Mickey Mouse Club as a child never in her wildest dreams would have thought she’d shoot to super stardom by reviving teen pop and be regarded as a pop icon. Britney Spears’ first studio album, Baby One More Time became an international success and it was uphill from then on. Her marriage to American dancer Kevin Federline was a whirlwind one and two months after giving birth to their second child, she filed for divorce. She went through a personal crisis, which caused her to lose custody of her children, but she was able to turn her life around eventually. They have tried to co-parent and were snapped attending their sons’ soccer match back in 2013. Federline was accompanied by his girlfriend.
9 Colin Hanks and Busy Philipps
As far as unlikely pairings go, not very many people know that Colin Hanks used to date Busy Philipps. It happened way before they became celebrities. Hanks is the son of Tom Hanks and is best known for his roles in the TV shows The Goof Guys, Roswell, and Band of Brothers. Busy Philipps, on the other hand, has appeared in the shows Dawson’s Creek and Cougar Town; and the films White Chicks and Made of Honor. Hanks and Philipps both attended Loyola Marymount University which was where they met and began dating. Philipps recently appeared as Kelly Ripa’s guest co-host in Live! With Kelly, where she got to interview Hanks. Hanks quipped that “it’s not awkward going on national television being interviewed by your old college girlfriend.” In fact, the pair have become such good friends, that their families even hang out together.
8 Heidi Klum and Seal
Everyone thought the romance between Heidi Klum and Seal was the stuff dreams were made of and hoped it would last forever. Klum was left by the father of her first child while she was still pregnant and Seal was her knight in shining armor who swooped in to be there for her when she gave birth. Seal later adopted Klum’s daughter after they got married. Sadly, the couple split after almost seven years of marriage and have both since moved on to other partners. The uncouple have maintained contact and a civilized relationship for the sake of their children and in August 2015, paparazzi snapped Seal leaning in and giving an awkward goodbye kiss to his ex after they had dinner with their kids in New York. The angle of the camera made it look like they were kissing the corner of each other’s mouths (when it was probably more of a kiss to the cheek), while Seal’s current girlfriend Erica Packer looked on.
7 Rihanna and Chris Brown
She has become a household name not just because of her unique name, but more so because of her music and her personal life. Rihanna hails from Barbados and can attribute her career beginnings to Jay z, whose label signed her up for a recording deal. She’s known for the songs, “Umbrella,” “Please Don’t Stop The Music,” “Take A Bow,” “Diamonds,” and so many more hits. Her romantic relationships have consistently been tabloid fodder as well, the most publicized of which was her tumultuous romance with Chris Brown. Brown was arrested for physically assaulting her and was given a restraining order against her. However, he was allowed to attend the same public events with her, as seen in this photo of them at a Summer Classic Charity Basketball Game. While Brown did his antics on the court, Rihanna, sitting a few feet away, was the only person whose eyes were averted from him.
6 Sofia Vergara and Nick Loeb
She’s known for her comedic prowess in the popular TV sitcom Modern Family, just as much as she is famous for her luscious curves and impeccable red carpet fashion style. Sofia Vergara’s very strong Colombian accent has also made her stand out from the rest of her peers and she has been nominated multiple times for her role in Modern Family. She was engaged to American businessman Nick Loeb in 2014, but the engagement was called off. Vergara is now married to Joe Manganiello after dating for six months. It was cringe-worthy to have to run into Loeb in a public event and in front of the cameras, but it happened at the New York Angel’s Ball. She was being interviewed by AJ Calloway when Loeb tapped her on the shoulder in greeting. She was caught off guard, but didn’t pay him heed, continuing with her interview like nothing happened.
5 James Cameron and Kathryn Bigelow
James Cameron is one of Hollywood’s most renowned directors, with films like The Terminator films, Titanic, and Avatar tucked under his belt. He has won Academy Awards for both Titanic and Avatar, which are the two highest-grossing films of all time at $2.19 billion and $2.78 billion respectively. Thanks to these two blockbusters, his net worth has ballooned to $257 million as of October 2010. Not very many people know that Cameron has been married five times and his wives include Linda Hamilton (by whom he has one daughter) and director Kathryn Bigelow. At the 2010 Academy Awards, Cameron and Bigelow were both nominated for their respective films, Avatar and The Hurt Locker. But it was Bigelow who took home the award and at the awards show, Cameron pretended to strangle Bigelow in mock anger. When caught in photos, it looked equal parts awkward and disturbing.
4 Taylor Swift and Joe Jonas
She’s known for writing songs about her failed relationships and friendships and whenever a new single of Taylor Swift’s is dropped, everyone starts wondering who she’s writing about. Some songs are obvious just by the title. “Dear John” is about her ex-beau John Mayer. “Style” is supposedly about another ex, Harry Styles. People speculate that “Shake It Off” is about Jake Gyllenhaal and “Bad Blood” is about her supposed falling out with Katy Perry. But we wonder, did she ever write a song about Joe Jonas? In case some may have forgotten, the two dated back in their teen years. Swift publicly slammed Jonas by saying in an interview that he broke up with her via a 27-second phone call. But it seems like they have buried the hatchet, as she gave her seal of approval when Jonas started dating her bestie Gigi Hadid years later. They even hung out a couple of times, along with Swift’s then boyfriend, Calvin Harris.
3 Orlando Bloom and Miranda Kerr
Miranda Kerr is one of the world’s most sought after models, having been a Victoria’s Secret Angel several times over. When she and Orlando Bloom started dating, their fans swooned because what an amazing gene pool those two had! They got married and have one son Flynn, but only a couple of years after he was born, the couple went their separate ways. But the two maintain a relationship for the sake of their son. And while we’re sure the exes are friendly, it’s still a bit disconcerting to have to interact with each other unprepared while in front of the cameras. A few months after they announced their divorce, Kerr was being interviewed at the post-Oscars Vanity Fair party, when Bloom came up to her to say hello, told her she looked amazing, and planted a kiss on her cheek. Kerr’s face turned beet-red and though she looked flustered, she continued with her interview like the pro that she is.
2 Harry Styles, Cara Delevingne, and Kendall Jenner
Being in one of the most popular boy bands in the world, the likes of which are sometimes compared to The Beatles, can guarantee you a flock of women constantly fawning over you. Harry Styles can thank his band One Direction for catapulting him to fame and paving the way for him to make it as a solo artist. He is also set to make his acting debut in the 2017 action thriller Dunkirk. He has been linked to many of Hollywood’s it-girls, including Taylor Swift, Kendall Jenner, and Cara Delevingne. Delevingne is friends with both Jenner and Swift, which can make for some awkward situations, especially when they run into their shared ex. Styles bumped into Jenner and Delevingne back in December 2014 at the British Fashion Awards in London. He seemed to play it cool, as he chatted with his two exes.
1 The Weeknd and Bela Hadid
He chose a unique and catchy professional name so that people would remember him and yes, the public certainly knows who the The Weeknd is. The Canadian singer gained fame by uploading several original songs to YouTube, leading to the 2013 release of his first studio album entitled Kiss Land. His career has skyrocketed since then and with his success came the usual disadvantages of being famous, namely having the media follow every detail of your personal life. Everyone knew he dated model Bella Hadid and that they split after a year of dating. They came face-to-face in the Victoria’s Secret runway a few weeks later, with Hadid smirking at her ex while she passed him on the runway as he serenaded the models. Some may have hoped that they would get back together, but he seems to be dating Selena Gomez now. Hadid wasn’t happy about it, as she unfollowed Gomez soon after news about the new couple broke.
Sources: nydailynews.com, huffingtonpost.com, mirror.co.uk, people.com
