Everyone knows what a bad idea it is to date your close friend’s ex. You could potentially torpedo not one, but two relationships. That is, unless all three of you proceed extremely carefully and communicate openly with each other. And these days, who has the time for that?
Things work differently in Hollywood. Actors go onto sets and spend all day making out with someone who isn’t their partner. They leave their family for six months to go shoot a new Marvel movie in England. They get paid so highly that and live under such scrutiny that if they want to date someone of equal social structure there’s really only a tiny pool of people to choose from. The potential for friends and exes to become tangled is incredibly high. And when it goes wrong, as these things so often do, it happens for all the world to see.
But we’re not here to shame, we’re here to learn. We’ve gathered together 15 legendary love triangles of the silver screen and beyond. How did the following stars deal with seeing their exes and friends together? Many of them handled their business with class, while others made huge mistakes, and in either case there are a lot of lessons we can take away.
Here are 15 Stars Who Dated Their Friends' Exes.
TOM CRUISE AND JAMIE FOXX DATED KATIE HOLMES
Since 2005, Tom Cruise has been clinging to the A-List by the tips of his fingers, largely thanks to leftover public resentment after a whirlwind yet somehow endless courtship of Katie Holmes. Before all that, in 2004's Collateral, Cruise played against type as a hitman who menaced Jamie Foxx all night long. Unlike in the film, Foxx bonded with Cruise as a friend, and would later provide a shoulder to cry on once TomKat came to an end in 2012. But in a huge surprise to those of us who saw the electrifying chemistry on display in Collateral, Jamie instead wound up with Katie.
Foxx and Holmes are an excellent example on how to handle a tricky situation.
You can’t help who you fall for, but the least you can do is avoid rubbing your new relationship in your ex’s face. The couple has tread very carefully, but a few too many pictures together at beaches and dinners have finally exposed them to the world. Even so, you’d be wise to follow their lead and at least try to keep a low profile, especially if you’re trying to keep Tom Cruise happy. You don’t want him to start looking at that old DVD of Collateral like it’s a How-To video.
OWEN WILSON AND LANCE ARMSTRONG DATED KATE HUDSON
It can flat-out suck when you find out that someone who broke your heart has moved on with another person. But if you’re feeling overwhelmed, Owen Wilson’s experience a decade ago might prove instructive; don’t be afraid to ask for help.
Wilson wound up in the hospital in mid 2007 after trying to take his own life. The exact circumstances that drove him to teh attempt are his own business, but it was public knowledge that he had just broken-up with Kate Hudson. Inn 2008, pictures of Hudson with Tour de France winner and future disgrace Lance Armstrong began to surface.
Armstrong had been a friend of Wilson’s, and had fittingly even put in a cameo in Wilson and Hudson’s 2006 third-wheel comedy You Me and Dupree.
Whatever heartache this relationship may have caused Wilson, by this point he had got himself into a better place. He was having his depression treated professionally and spending lots of time on the phone with a supportive family, including his brother Luke. In the ten years since, Wilson has had two children, and Hudson too has recently announced that she’s expecting a third child. Armstrong, meanwhile, has others things on his mind.
KATE BECKINSALE AND SARAH SILVERMAN DATED MICHAEL SHEEN
Sometimes we get a story in which everyone is just the best. To anyone who is stuck in a potentially thorny love triangle, look to Sarah Silverman, Kate Beckinsale, and Michael Sheen as role models. They’ve handled their business with grace and good humour. They are our last, best hope.
Sheen and Beckinsale had an eight year relationship and a daughter before their split in 2003. Beckinsale went on to marry her Underworld director Len Wiseman, and The Masters of Sex star Sheen later found happiness with stand-up comedian Sarah Silverman. Much to the dismay of those who witnessed their playful chemistry in venues like Doug Loves Movies, the couple called it quits in 2017, citing the difficulties involved in maintaining a long-distance relationship.
Silverman good-naturedly commiserated with Beckinsale over their shared ex on Instagram, making light-hearted jokes about shared comfort food (they recommend you microwave your M&Ms, folks) and about how insensitive it was of her to announce the break-up on Sheen’s birthday.
Meanwhile, Beckinsale is fresh off a career resurgence as a result of Love & Friendship, Silverman’s got her own Hulu talk show I Love You, America, and Sheen has landed a plum role in next year’s adaptation of Good Omens. It would seem there’s no need to feel badly for any of these three stars either personally or professionally.
GWYNETH PALTROW AND DREW BARRYMORE DATED LUKE WILSON
Here's a fun fact: Drew Barrymore and Gwyneth Paltrow share a godfather in Steven Spielberg. Both actresses got their start in Spielberg's E.T. and Hook (respectively), and although we can’t be sure exactly when their paths first crossed, the god-siblings(?) have a long-standing friendship going back to at least the '90s, when they ruled Hollywood.
For two years, Barrymore had dated Luke Wilson, and their break-up was so amicable that Barrymore had no problem casting Wilson in a little movie she was producing called Charlie’s Angels - albeit as Cameron Diaz’s love interest, not her own. Shortly after, Wilson was linked for a time to Paltrow, right on the heels of their co-starring roles as a romantic pair of adopted siblings in 2001’s The Royal Tenenbaums.
If this relationship ever caused any kind of strife between Paltrow and Barrymore, the two actresses have never let on.
Over the years they’ve been photographed having a great time together at bachelorette parties and baby showers. And whatever a Goop Summit even is, they’ve attended that together too. When your friendship is on a foundation that firm, sometimes a little thing like having the same ex only matters as much as you let it matter.
KIEFER SUTHERLAND AND JASON PATRIC DATED JULIA ROBERTS
After they met on 1990’s Flatliners, Kiefer Sutherland and Julia Roberts were set to tie the knot just one year later. But on the day of the wedding, Roberts had absconded to Ireland with Sutherland’s good friend and fellow lost boy, Jason Patric. Roberts had left her fiancé behind not long after rocketing to the top of the Hollywood elite with the smash hit success of 1990’s Pretty Woman.
Despite being relegated to small supporting roles through the '90s, Sutherland was nothing but magnanimous when his old co-stars came up in a 2016 appearance on The Jess Cagle Interview: “It wasn’t what she wanted to do in the end. And I think it took a lot of courage in amongst all of that other stuff to be able to say, ‘I can’t do this.’”
If that seems gracious, it’s because living well can be the best revenge. Sutherland became an early adopter of the idea that film actors can forge a path back into the public consciousness through television, spending nine seasons and the better part of thirteen years in the iconic role of Jack Bauer on Fox’s 24. Patric, on the other hand, is still mainly known as the guy who replaced Keanu Reeves in Speed 2. Not that we’re taking sides.
TAYLOR SWIFT AND SELENA GOMEZ DATED TAYLOR LAUTNER
Quick sidebar: it’s also probably a bad idea to get serious with someone who has the same name as you. Nothing to do with ego or wanting to date a mirror image of yourself - sorry, what were we talking about? It’s really just that the simple logistics of it are just a nightmare. A Taylor Swift/Taylor Lautner coupling was probably doomed before it got off the ground.
For a number of years, anyone interested in finding information on the rumoured Taylor/Taylor/Selena triangle had their work cut out for them. When asked about the relationship in 2009, Gomez deftly talked her way around the question, claiming she was single even as she praised Lautner effusively. It wasn’t until years later that Lautner revealed in a Scream Queens Facebook livestream that Swift’s break-up single “Back to December” (released in 2010) was all about him.
Anyone trying to figure out the exact timeline is probably out of luck, but the friendship between Gomez and Swift goes all the way back to when they were each dating a different Jonas Brother in 2008. Both singers handled the situation far more skillfully than most of us would have if we were in the spotlight at that age.
NIKKI REED AND NINA DOBREV DATED IAN SOMERHALDER.
21st century franchises involving vampires have trended towards the sort of melodramatic romance that’s inherent in any story about monsters who must lure unsuspecting victims to survive. 2009’s The Vampire Diaries was one such series, depicting a human/vampire relationship that would spill into the real world as stars Nina Dobrev and Ian Somerhalder dated for nearly four years.
After splitting up with Dobrev in 2013, Somerhalder then became engaged to Twilight vet Nikki Reed.
Upon hearing about a potential love triangle that involved not one but two YA vampire series, the tabloids ascended to a level of ecstasy that no fictional vampiric glamour could ever hope to induce, and immediately set to work trying to create drama where no drama existed.
Dobrev and Reed pushed back against accusations of long standing tension in a 2017 Instagram post depicting a pleasant dinner they were having along with Somerhalder, taken as Dobrev returned to film The Vampire Diaries finale. She was content just to express her happiness that she was catching up with the married couple, but Reed went further, taking the tabloids to task after years of silence.
“Who wants to respond to made up stories about friends backstabbing friends, cheating exes, or cast members exiting shows on low-brow websites like Hollywood Life that are just perpetuating trends that preceded us. Yuck.” Shots. Fired.
DREW BARRYMORE AND KRISTEN WIIG DATED FABRIZIO MORETTI
Imagine that you have a close friend who not only does a great impression of you, but does a great impression of you on Saturday Night Live. Now imagine finding out that your friend who can do a great impression of you is dating your ex-boyfriend, then brace yourself for the absolute tidal wave of horrifying implications that come with it. You probably wouldn't deal with it as coolly as these three celebs did.
It’s such a specific situation that most of us will never have to deal with, so there’s probably no reason to look for some kind of life lesson from the Drew Barrymore/Kristen Wiig/Fabrizio Moretti triangle, but these two friends certainly handled the whole mess with aplomb.
In an interview with Allure, Barrymore acknowledged the strangeness of the situation, yet she was quick to express her happiness for the couple. “It all seems so wacky.... but that’s kind of how life works. It seems fitting that they would find each other. I was like, ‘Right, of course, that makes perfect sense.’”
Imperfectly, however, Wiig and Moretti were not to last, they parted in mid-2013. All of these splits were amicable, though. Both Barrymore and Wiig have spoken well of Moretti post-breakup and continue to count him as a friend.
DIANA AGRON AND EMMA ROBERTS DATED ALEX PETTYFER
Another strategy should you find yourself being scrutinized for dating a friend’s ex; a simple “No comment” will often suffice.
The facts are these: Magic Mike star Alex Pettyfer told US Weekly that he had no regrets about having an ex’s name tattooed on his ring finger. That ex was none other than Wild Child Emma Roberts, Pettyfer’s co-star in the 2008 film. People Magazine reported that in 2010, Glee’s Diana Agron had moved out of the house she and Pettyfer had shared after a rift developed between the two upcoming stars. And The Daily Mail’s report on a These Girls Glamour Magazine event had photos of Agron and Roberts attending together and performing onstage alongside the likes of Amy Poehler and Amy Schumer.
So we’ve got these three separate reports on three separate relationships. Given all that, what kind of drama exists between Agron and Roberts? As far as anyone can tell, there is none.
It’s difficult to say exactly when their friendship began, but both starlets had dated Pettyfer years before they share the stage at a Glamour event.
Whether their shared ex was a source of friction or something that was completely in the rearview mirror, we will never know due to the miracle that is tactful silence.
JENNIFER ANISTON AND COURTENEY COX DATED ADAM DURITZ
Considering the name of the show they starred on, it was inevitable that we’d get around to Jennifer Aniston and Courteney Cox. Both actresses met on the set of Friends and formed a firm bond, one that the likes of Counting Crows frontman Adam Duritz could never hope to shatter.
Duritz and Aniston dated in 1995, and after a brief time together they opted not to go on a break but instead to split up entirely. Two years later Duritz pivoted to Cox but that didn’t last long either.
You’d assume this might cause some conflict, and the tabloids circled like vultures, waiting for the day they could start writing ironic headlines about how the cast of Friends was anything but. But for a show that had such a highly paid cast and so many rising stars, the cast remained remarkably close. No one more so than Aniston and Cox, who have continued to stay in each others lives since the show’s end in 2004.
Adam Duritz, for his part, although he regrets the negative attention the two relationships brought to him and his band, harbors no ill will. “They were nice girls and I went out with them and that was that.”
CAMERON DIAZ AND BRITNEY SPEARS DATED JUSTIN TIMBERLAKE
We, as a culture, weren’t prepared to talk about mental illness in the mid-00s. Which means that we weren’t prepared to deal with Britney Spears, whose struggle was so high-profile an entire South Park episode was devoted to it. Her every move was so scrutinized it’s hard to believe that any detail of Spears’ life slipped by the press, but incredibly a new question emerged last year: have Britney Spears and Cameron Diaz been friends this whole time?
A lot of us who were teenagers in the early aughts probably couldn’t tell you what year the 2004 Presidential Election took place in, but we certainly remember where we were when Britney Spears and Justin Timberlake broke up. After that, Timberlake and Diaz wound up dating for three years, and when that ended it all seemed doomed to the scrap heap of history.
That is, until Britney Spears unfathomably reposted a nearly year old Instagram photo of Diaz’s tomato garden, offering unsolicited admiration of the actress that dated back to 1998’s There’s Something About Mary. Diaz has likewise praised Spears’ onscreen presence and vocal talent.
It’s all too easy to hold a grudge against your ex’s ex, regardless of how well you actually know each other. So this mutual Spears/Diaz praise-fest from afar is highly refreshing.
MATT HARDY AND THE EDGE DATED LITA
While we’ve been chatting so enjoyably about exes dating friends in real life, this exact situation is often the fuel that drives major conflict in the WWE. After all, if two people are going to physically fight each other, what motivation is more compelling than someone who’s been betrayed by his girlfriend and his best friend?
In 2005, Lita, The Edge, and Matt Hardy found themselves in this exact situation outside the confines of the wrestling ring, and were approached by the WWE about turning their real-life drama into a storyline for the cameras. In an interview on Lilian Garcia’s podcast, Lita, real name Amy Dumas, reflected on what had happened.
Dumas and Hardy had been disconnected from each other’s lives after she was on her back from an injury, and while they were separated she bonded with Edge: “I know both of us were kind of like, ‘Oh ****, you know once we started to realize […] we were more than just two bros hanging out.”
If you’re in a situation where your partner is cheating on you with your friend, there’s a way to calmly process what you’re feeling and eventually heal. Failing that, find a way to monetize your pain. It’s that kind of a world.
TAYLOR SWIFT AND KATY PERRY DATED JOHN MAYER
Passive aggressiveness is the enemy of all friendships. And for almost a decade all sorts of inferences and implications have been flying back and forth between Taylor Swift and Katy Perry.
The two singers started out on the right foot, exchanging friendly tweets and appearing in numerous photographs together. Then, Perry dated Swift’s ex John Mayer.
In the years since, the two have said whatever the feud between them is, it has nothing to do with a man.
Examination of their history does indeed seem to reveal that Mayer is a symptom of their conflict, not the cause. There’ve been oddly pointed song lyrics, there’s been shade in interviews.
“Watch out for the Regina Georges in sheep’s clothing…” tweeted Perry.
Swift put her entire back catalogue on Spotify the exact same day Perry put out a new album. Perry hired three backup singers right out from under Swift right in the middle of her world tour. In a recent interview on The Thrive Global Podcast, Perry acknowledged the feud directly and publicly apologized, saying that in these times women need to start showing solidarity. It’s a beautiful thought, but it’s not the first time a truce has been called for.
Frankly when it comes to Hurricane Perry-Swift, we might only be in the eye of the storm.
Sorry, John who?
GEORGE HARRISON AND ERIC CLAPTON MARRIED PATTIE BOYD
This is one for the ages - a story so romanticized you feel as though you must have seen it in a movie at some point. Eric Clapton had fallen desperately in love with Pattie Boyd, the wife of his fellow musician and good friend George Harrison. Boyd acted as a sort of unwilling muse to Clapton, turning down his advances even as she became the subject of many of his songs. We would not have “She’s Waiting” or “Wonderful Tonight” if not for Clapton’s unrequited love.
Misfortune struck all parties involved during the early '70s. Clapton’s addiction sent him into isolation and Harrison and Boyd split up. But after Clapton kicked his bad habit, Harrison gave the couple his blessing and they were to be married five years later. Harrison was in attendance at their wedding (during which he had a mini Beatles reunion with Paul and Ringo), but Clapton threw it all away when his habit of philanderin led Boyd to divorce him in 1988.
It’s a sad and, at times, very romantic story that spans many ups and down over two decades, but in a refreshing twist, none of the drama seems to have stemmed from hard feelings between Clapton and Harrison.
ELIZABETH TAYLOR AND DEBBIE REYNOLDS MARRIED EDDIE FISHER
It’s the original love triangle, from a time in which the paparazzi had to etch celebrity sightings on stone tablets. Back in 1958, Singin’ in the Rain star and national treasure Debbie Reynolds famously saw her husband in the arms of Elizabeth Taylor. They had once been neighbours and inseparable friends, but as summed up by daughter-of-national-treasure-and-national-treasure-herself Carrie Fisher, Eddie Fisher had initially set out to console Taylor after the passing of her husband Mike Todd. Initially.
“Naturally, my father flew to Elizabeth’s side, gradually making his way slowly to her front,” wrote Carrie Fisher in her 2001 memoir.
Debbie and Eddie were never to reconcile, with Reynolds asserting that her ex-husband had no interest in the children they had together. But by happenstance, Reynolds and Taylor wound up on the same ocean liner in 1966, and decided to rip off the bandaid and talk things out over dinner. Their rekindled friendship lasted for four and half more decades, and the two even starred together in the Carrie Fisher scripted 2001 film These Old Broads.
It just goes to show you should evaluate these situations on a case by case basis. If someone in your life is a toxic presence there’s no need to stay in touch with them, but an olive branch is always worth considering.
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Did we miss any celeb friends who dated each other's exes? Let us know in the comments!