The world of celebrities is actually quite small, with starlets and heartthrobs running in the same circles and being thrust together through various projects and Hollywood events. It was inevitable that there would be a love match or two, however brief the encounter. Shows like HBO’s Entourage gave an inside look into the dating habits of stars in Hollywood, and many seemed more like a flyby fling rather than anything truly substantial.
Actors and musicians often seem to have an increased difficulty in staving off divorce, and oftentime celebrities are known more for how brief their marriages were rather than how they’ve managed to hold it together. From Britney Spears' annulled marriage in Vegas to Kim Kardashian’s 72-day marriage to Kris Humphries, all too often celebrities are known for jumping from one bed to the next.
While this seems like the worst case scenario for the reputation of a Hollywood starlet, sometimes even the most happily married celebrity couples can end up in the category “been there, done that.” The media frenzy that follows a celebrity couple only leads to increased scrutiny of their daily lives, and can create a storyline for the public that imprints on their psyche. From cheating allegations that can ruin a celebrity’s reputation to the seemingly “perfect” couple’s divorce that shocks the world, sometimes it’s the longest running and more memorable couples that cause the most damage to their public persona. Check out some of the 15 sexiest sloppy seconds in Hollywood, and see how their former relationships have greatly impacted the way they were viewed from then on.
15 Jennifer Aniston
When Jennifer Aniston married Brad Pitt in 2000, she was one of the biggest stars on television. Pitt was becoming much more prominent on the big screen, and Aniston was starting her seventh season on the hit television series, Friends. On the red carpet, they were red carpet royalty and a favorite among viewers. After Pitt starred alongside Angelina Jolie in Mr. & Mrs. Smith, rumors started to fly about their onscreen chemistry. Shortly after the infamous W pictorial spread, Aniston and Pitt announced their divorce and made the world take sides. The Team Aniston vs. Team Jolie debate just prolonged the intrigue over the demise of Aniston’s first marriage. After being portrayed as the poor, passed-over first wife, the public craved to finally see Aniston happy again. It seemed that every new man on her arm was compared to Brad Pitt, and there was always immense pressure to finally give Aniston her fairytale ending. After a three-year engagement, Aniston ultimately made it down the aisle with Justin Theroux. The intense media scrutiny continues, with tabloids inevitably referencing her first failed marriage. Regardless of who the next man would be, it’s got to be hard being compared to Brad Pitt.
14 Kristen Stewart
When Kristen Stewart began dating Robert Pattinson while filming the first film in the Twilight series, the world went into a frenzy thinking there was a real life romance between Bella and Edward. Paparazzi clambered to find concrete proof of their relationship, and fans seemed to love the idea of their favorite onscreen couple getting it on in real life. Yet, the dream came to a slamming halt when photos were released of Stewart getting intimate with her married Snow White and the Huntsman director. After some back-and-forth, Pattinson and Stewart ultimately split in 2013. Since then, the only person that has truly been linked to Stewart is Alicia Cargile. Stewart gave an interview with The New York Times Style Magazine, stating, “I would never talk about any of my relationships before, but once I started dating girls it seemed like there was an opportunity to represent something really positive.” There’s no word whether or not Stewart will ever go back to dating men, but whoever it is has some pretty big shoes to fill to reach the status set forth by Edward and Bella’s love.
13 Miranda Lambert
Country music has always been an industry that loves couples that stay together. From Garth Brooks and Trisha Yearwood to Faith Hill and Tim McGraw, country fans are a sucker for a good romance. So, when Miranda Lambert and Blake Shelton were married, people loved the idea of the next generation of a country love story. As regulars on the red carpet, Shelton often spoke lovingly about his wife while in the swiveling chair on The Voice. When the couple announced their split, it was difficult to find out the truth behind the demise of their marriage. Some reports claimed that Shelton was cheating with a younger country starlet, while others claimed it was Lambert that had been stepping out. While Shelton moved on pretty quickly with his costar, Gwen Stefani, Lambert hasn’t yet settled down with anyone in particular. She had achieved huge success as Blake Shelton’s wife, and the pair even sang together on numerous occasions. While Lambert is still considered one of the hottest females in country music, it doesn’t seem like there are many willing to jump into the ring of this he said/she said media circus.
12 Katie Holmes
When Tom Cruise jumped on the couch of The Oprah Winfrey Show in an attempt to proclaim his love for Katie Holmes, audiences didn’t exactly find it endearing. Instead, the public started to look at Cruise with a look of confusion, since this was just another example of Cruise’s outlandish behavior in recent years. When the two ultimately split in 2012, people assumed it would be Cruise to move on quickly with the next willing Hollywood starlet. Yet, it was Holmes that seemed to move on with her love life. Speculation surrounding her relationship with Jamie Foxx first came to light when the pair was seen dancing together at a 2013 charity event, but things really hit the fan when photos were leaked to tabloids showing the pair holding hands in a private setting. Tabloid reports continue to come out stating the pair are engaged, had a secret wedding, and that Holmes is pregnant with his baby; yet, neither have ever publicly announced that they are romantically involved. Regardless of her relationship status with Foxx, Holmes will most likely never shake the fact that she was once Cruise’s main squeeze and the mother of his biological child, Suri.
11 Sofia Vergara
Sofia Vergara was once a staple figure on the red carpet with her fiancé, Nick Loeb, and even gushed about his elaborate proposal on such daytime talk shows as The Ellen DeGeneres Show. By taking to social media and flaunting their most intimate and playful moments together, it seemed like theirs would be an everlasting love. Yet, within a very short amount of time, the couple announced their split and she was immediately romantically linked to Joe Manganiello. This couple actually made it down the aisle, despite the embryo drama involving her ex. Loeb and Vergara had created two embryos in 2013, and Loeb was fighting the courts to allow him to impregnate a surrogate with the embryos. This seems like an awful lot of baggage for Manganiello to take on, especially since Vergara didn’t even end up marrying Loeb. However, Vergara was previously married when she was 18-years-old, and her son, Manolo, is 23-years-old.
10 Brandi Glanville
Brandi Glanville was a regular on the red carpet when she was on the arm of her then-husband, Eddie Cibrian. The two were married for nine years, and had two sons together. Their split came after a highly publicized affair that left two marriages in ruins. Cibrian began an affair with LeAnn Rimes while the pair was on set of a Lifetime film, and both subsequently divorced their spouses and married each other. While the ex-husband of Rimes has pretty much stayed out of the limelight, Glanville has been on the pity party bandwagon ever since her divorce was finalized. It was a regular storyline when she was on The Real Housewives of Beverly Hills, and it’s a constant source of contention when she speaks about infidelity, motherhood, and pretty much anything else. Since her divorce, Glanville has been linked to a number of men, including some of the hottest leading men in Hollywood, Yet, none have expressed any interest in putting a ring on it, and few have stuck around long enough to ever even be considered a “boyfriend.”
9 Gwen Stefani
When Gwen Stefani and Gavin Rossdale walked down the aisle, the public was overjoyed at what a perfect couple they were. Both were members of two of the hottest bands from the '90s, and both went on to start a solo career. While Bush’s Gavin Rossdale didn’t have such a booming career throughout their marriage, Stefani became even more popular in music and was able to branch out into other avenues. From her successful fashion line to becoming a favorite judge on The Voice, Stefani was hitting yet another peak in her career. So, when news broke about the philandering on behalf of Rossdale, the public immediately took Stefani’s side. There had been rumors about Rossdale for years, and after numerous denials Rossdale finally admitted to “experimentation” in his earlier years. Stefani didn’t seem to care much for these swirling tabloid headlines, but couldn’t dismiss Rossdale’s affair with their nanny, Mindy Mann. After 13 years of marriage, Stefani didn’t stay on the market long before being swooped up by Blake Shelton. The two have captured the hearts of viewers, even though they’re both recently divorced. Shelton doesn’t seem to mind that Stefani’s first husband was “experimental.”
8 Nicole Kidman
When Nicole Kidman and Tom Cruise once walked the red carpet together, they were the epitome of Hollywood’s A-list. The pair had starred together in a number of films, and the world seemed to be rooting for their love. So, when it was announced that the couple had split after ten years of marriage, people were in disbelief over the loss of their favorite celebrity couple. Cruise was able to move on to a much younger (and submissive) starlet, Katie Holmes, and Kidman moved on as well. Marrying fellow Aussie, Keith Urban, Kidman seemed to start a brand new life for herself. While she had two children with Cruise, she went on to have her first biological children with Urban (through a surrogate). The couple has been very vocal about their love for one another, with Urban even dedicating songs and albums to Kidman in a gesture of professed love. Although the two seem very happy together, people can’t help but remember that she seemed just as happy with Tom Cruise (before they split).
7 Elin Nordegren
When Elin Nordegren was first married to Tiger Woods, she became known to the world as the ultra-glamorous former model that seemed right at home on his arm. Their romance seemed less like a whirlwind and more like the stuff of the Joneses. While Tiger Woods was reaching the height of his success on the golf course, Elin was the picture of a doting wife and mother. But when mistress after mistress started to come out with allegations of infidelity, the public started to look at Tiger Woods in a whole new light. Elin became the betrayed and jilted wife, and Tiger Woods became the sex-crazed adulterer that couldn’t manage to hang on to a good thing. The affairs wreaked havoc on Woods’ reputation, and people wondered whether or not Elin would ever find love again. Not too many men would jump at the idea of starting a relationship with a woman with such a messy and publicized divorce, but billionaire boyfriend, Chris Cline, seemed up for the challenge. In March 2016, photos were released showing the couple sneaking a quick kiss while on the ski slopes of Switzerland. Let’s just hope she releases her trust issues from her former marriage.
6 Gwyneth Paltrow
It isn’t a new concept for a film actress to fall in love with a musician, and in the case of Chris Martin and Gwyneth Paltrow it seemed like a good fit. Paltrow has always been musically inclined, singing in the hit film, Country Strong, and even singing a duet with Cee Lo at the Grammy’s. The couple seemed terrifically happy, raising their children, Moses and Apple. In recent years, Paltrow has gained quite a reputation in the eyes of the public, especially since her Goop site seems completely outside of reality for those outside of the celebrity world. After 11 years of marriage, Paltrow filed for divorce and the Internet finally got to see what it meant to “consciously uncouple.” Although they both claim it was an amicable split, and they are still a family in raising their children, it will be interesting to see who will be willing to be the next Mr. Gwyneth Paltrow. Famously drinking a $200 smoothie each morning, having two kids and an ex-husband she still refers to as part of her “family,” isn’t exactly a recipe for transitioning well to finding a new husband.
5 Amber Rose
When Amber Rose was first seen on the arm of Kanye West on the red carpet, she gave off an air of mystery and sex appeal. From the fact that she rarely spoke to the signature blonde/bald look, people became increasingly intrigued over this new odd beauty on the Hollywood scene. When more details emerged about Rose and her former stripper status, people seemed even more interested in this woman that completely owned her past and her sex appeal. After their split, it shouldn’t have surprised the public that Rose would remain a celebrity figure. No longer needing Kanye West to get her into red carpet events, she quickly moved on to rapper Wiz Khalifa. Khalifa didn’t seem to mind being where West had once been, but Kanye definitely had a few choice words for him on social media sites. West and Khalifa had a very public feud online, with one tweet stating, “You wouldn’t have a child if it wasn’t for me.” Referencing if it wasn’t for him, Khalifa would never have even had the chance to meet Amber Rose; it might just be Kanye that has the biggest problem with his sloppy seconds being passed on.
4 Mila Kunis
Although Ashton Kutcher may have been Mila Kunis’ first kiss back when the pair starred on That 70’s Show, that doesn’t mean he was her true first love. While the world already knows about Kutcher’s relationship with Demi Moore, not everyone is aware of the details surrounding the personal life of Kunis. Kutcher seemed to get hounded by the paparazzi due to the whole cougar fascination surrounding his relationship with Demi, and because of how well he seemed to integrate into their family dynamic. Yet Kunis kept her private life a secret to the general public. For those not in the know, Kunis began dating Macaulay Culkin when she was just 18-years-old. The two were together for eight long years before they split. Kunis opened up about the difficulties in dating Culkin, citing much of the drama came from the intense amount of fandom Culkin received even just in walking down the street. Yet the biggest shocker about their relationship was how Culkin landed Kunis as a girlfriend in the first place. From the emaciated look to the deep-set wrinkles in his face, Kutcher should have been at least a little repulsed at what constituted her most serious relationship.
3 Eva Longoria
When Eva Longoria began dating French professional basketball player, Tony Parker, people couldn’t help but notice how in love she seemed. While promoting her series, Desperate Housewives, she was often seen in interviews proclaiming how willing she was to fly back and forth to watch Parker in games and return back to film scenes for the show. Once the two were married, it seemed like her fairytale ending had been written. Yet the two ultimately divorced due to a highly publicized cheating scandal involving the now ex-wife of former teammate Brent Barry. The public couldn’t believe someone would actually cheat on the ultra-sexy Eva Longoria, especially when she was so adamant about being over-the-top in love with the French basketball player. After their split in 2010, it didn’t seem like Longoria was in a rush to remarry. Yet, when the president of the largest media companies in Latin America proposes, it’s a little difficult to say no. Longoria married José Bastón in March 2016, and the two shared a lavish wedding with all of Hollywood’s celebrities in attendance.
2 Amber Heard
While Amber Heard has acted in a number of highly successful films and television roles, many of her portrayals have been a bit obscure. She only gained real fame when she became romantically linked to Johnny Depp. Depp has continued to make it to the top of every list of hot Hollywood men since he was first seen on screen, and has become even more successful in recent years. Once the two were married, it seemed he had finally found happiness with this blonde bombshell actress. Yet their marriage wasn’t a union fit for fairy tales, and has since dissolved into a media frenzy with allegations of abuse. Heard accused Depp of physical and verbal abuse, but Depp has adamantly refused these claims. Numerous celebrities came out in support of Depp, and Heard’s character has been assassinated in the eyes of the public. While the pair is still entwined in a heated feud, the intrigue over the state of their marriage has only perpetuated a negative aura around this young Hollywood beauty. Because of all the media attention, it’s inevitable Heard will always be associated with the drama surrounding this marriage.
1 Heidi Klum
Heidi Klum has had love in her life before, but it wasn’t until she married music sensation Seal that she truly became part of a celebrity couple. It seemed that every step of their marital journey was documented for the entire world to see, and media stories included ultra-sappy stories like Seal proposing in an igloo. The couple had exceedingly lavish annual vow renewals, and were known for their equally elaborate couple’s Halloween costumes. Their divorce proceedings became surprisingly ugly, with Seal’s team claiming infidelity and Klum’s team accusing Seal of overly aggressive behavior. Since the couple split, Heidi became romantically linked to the much younger Vito Schnabel, the millionaire art dealer. Schnabel has been previously linked to a number of beautiful older women in Hollywood, including Elle Macpherson and Demi Moore. Only time will tell if he is truly serious about settling down with Klum, but perhaps he is a little turned off by the drama from her marriage with Seal. Plus, it’s got to be difficult living up to a woman that is used to such over-the-top declarations of love.