Here’s a list of celebrities who have navigated the tricky waters of dating the same people, some more gracefully than others!
Miley Cyrus: Liam Hemsworth & Kaitlynn Carter
Miley Cyrus and Liam Hemsworth fell in love on the set of “The Last Song” in 2009. They confirmed their romance with a PDA-filled goodbye at the airport after filming ended. Hemsworth proposed with a 3.5-carat ring in 2012. Their engagement was plagued by rumors. Eventually, the rumors proved true through social media in 2013.
Not long after breaking up with Hemsworth, photos surfaced showing Cyrus and Kaitlynn Carter from "The Hills" locking lips during a girls’ trip to Italy. From that point on, they were spotted together in various locations, from L.A. to NYC, but they never publicly confirmed their relationship status. Reports later revealed that the couple had decided to end things.
Cody Simpson: Gigi Hadid & Miley Cyrus
Cody Simpson and Gigi Hadid first laid eyes on each other in 2013 while filming the music video for his song "Surfboard." They were soon caught up in a passionate on-again, off-again romance for two years before finally calling it quits in May 2015. According to a statement from Hadid's rep, the split was all about giving each other space to pursue their individual goals.
In 2019, Miley Cyrus started dating Cody Simpson after her split from Liam Hemsworth. They shared their romance on social media, but things went sour when Simpson was caught kissing another woman while still with Cyrus. By August 2020, they had broken up. Simpson confirmed the split, calling it a mutual decision.
Nick Jonas: Miley Cyrus & Selena Gomez
First loves are special, and Nick Jonas found his in Disney darling Miley Cyrus. They started dating at 13 years old after meeting at a charity event in 2006. However, the couple split by the end of 2007. Cyrus channeled her heartache into writing her hit song "7 Things." Incredibly, the two remained friends and even collaborated musically.
Jonas later met Selena Gomez when she was rocking it as Alex Russo on "Wizards of Waverly Place." Even though they tried to keep their relationship under wraps, the internet soon found out. Cue the most talked-about social media feud between Gomez and Cyrus! Gomez quickly cleared the air, explaining they weren’t rivals, just two teenagers who liked the same guy!
The Weeknd: Bella Hadid & Selena Gomez
It's been a tumultuous journey for Bella Hadid and The Weeknd since they first connected in 2015. Even though rumors of a reunion continue to swirl, the two have yet to officially get back together. Despite the ups and downs, their love story has left its mark on The Weeknd's music in the form of his album "After Hours".
Selena Gomez and The Weeknd dated for ten months, rebounding from their respective relationships with Justin Bieber and Bella Hadid. While together, they traveled the world for The Weeknd's tour, and he even rearranged his schedule to be by Gomez's side during her kidney transplant. They have since moved on from each other, back with their exes, and onwards from there.
Justin Bieber: Selena Gomez & Hailey Baldwin
In 2009, a young Justin Bieber revealed that he had a major crush on the stunning Selena Gomez. Their first public appearance as a couple at the Vanity Fair Oscars party in 2011 set off a frenzy among fans. But as their fame continued to skyrocket, so did the pressure on their relationship. They broke up in 2013, marking a 5-year-long rollercoaster ride of breakups and reconciliations.
Hailey Baldwin married her childhood celebrity crush. Their relationship started with a backstage meeting at one of Justin's concerts. They then went from being friends to mutual crushes, and eventually lovers. After a brief split and a surprise engagement, the couple tied the knot in a private courthouse ceremony in 2018.
Taylor Lautner: Selena Gomez & Taylor Swift
Selena Gomez and Taylor Lautner had a brief romance in 2009 after meeting thanks to Kirsten Stewart, but unfortunately, didn't stick it out. The singer explained in an interview that they just wanted to hang out, go bowling, and have fun, but the paparazzi made it difficult. Gomez and Lautner remained friendly despite public scrutiny. At least they avoided any drama!
Taylor Swift and Taylor Lautner shared the screen as high school sweethearts in the romantic comedy "Valentine's Day" back in 2009. Their onscreen romance quickly turned into a real-life fairytale, with fans naming their relationship "Taylor Squared." And while their romance eventually fizzled out, Swift and Lautner have spoken fondly of each other in the years that followed.
John Mayer: Taylor Swift & Katy Perry
Let’s go back to March 2009. Swift, 19 years old, caught Mayer's attention, and they released a duet called "Half of My Heart." They performed it together at New York's Jingle Ball in December, where their chemistry was palpable. The couple reportedly came to an unhappy ending in February 2010. Swift later released the song "Dear John," alluding to their harsh breakup. Mayer responded with his own song, "Paper Doll," in 2013.
Katy Perry and the guitar god had a relationship on and off, from 2012 to 2015. What really made waves was when Perry ranked Mayer as her number-one bedroom partner over her ex, Diplo, and her fiance Orlando Bloom. Talk about steamy!
Calvin Harris: Ellie Goulding & Taylor Swift
Calvin Harris is no stranger to dating some of the most famous ladies in the world. When he and Ellie Goulding locked lips in his music video for "I Need Your Love," rumors started to fly. Despite the buzz, Goulding insisted that they were just friends, however, she ended up playing matchmaker and introduced Calvin to Taylor Swift. Her matchmaking skills blessed us with the epic Taylor/Calvin collaboration, "This Is What You Came For."
Once lovers, now enemies, Swift and Harris' whirlwind 15-month romance ended in 2016, with a social media announcement. Things turned sour when Swift started dating Tom Hiddleston soon after their breakup, and she allegedly made references to her past relationship with Harris in her next projects.
Ellie Goulding: Niall Horan & Ed Sheeran
Back in 2013, Niall Horan was just starting out, and Ellie Goulding was already a chart-topping sensation when their brief romance made headlines. The pair went on a few dates, and according to Goulding, it was a blast. Although the relationship didn’t pan out, Goulding has always considered Horan a true friend.
Ellie Goulding and British musician Ed Sheeran were seen holding hands at the 2013 MTV Video Music Awards. That brief moment was enough to spark rumors of a possible romance. While Goulding denied any romantic involvement, Sheeran later revealed that they were briefly an item. Sheeran's single "Don't" fueled more speculation and the grapevine was rife with rumors that Goulding had cheated on Sheeran with Horan.
Cara Delevigne: Harry Styles & Ashley Benson
Model and actor Cara Delevigne has been linked to several fellow A-listers. One of her earliest rumored relationships was with musician Harry Styles. By 2013, reports began circulating that the One Direction star was pursuing her with intentions of exclusivity. Their romance appears to have been short-lived.
Delevigne’s most long-lasting relationship to date has been with actor Ashley Benson. The pair were first spotted together in August 2018, sharing a kiss at an airport and going public with their relationship on Instagram soon after. Unfortunately, their love story ended in 2020, with a source stating that their relationship had run its course after several ups and downs.
Harry Styles: Taylor Swift & Cara Delevingne
Back in 2012, Taylor Swift and Harry Styles (aka "Haylor") briefly dated. They first met at the Kids Choice Awards and when Styles later visited Swift during her "X Factor" rehearsals, the two were looking cozy. A year later, Swift left the Caribbean alone on what was supposed to be a romantic vacation with her beau. It was later confirmed that they had split.
According to reports, Harry Styles was secretly dating model Cara Delevingne in 2013. Interestingly, this was not the first time that Harry and Cara were linked romantically. Back in 2012, rumors were flying about the two of them just before Harry went public with Taylor Swift. They have never denied or confirmed the relationship.
Natalie Portman: Moby & Jake Gyllenhaal
Acclaimed actor Natalie Portman is one of Hollywood's most beloved actresses, and her love life has also been a subject of interest to many. One of her most publicized relationships was with musician Moby, with whom she had a brief fling in 2001. Despite the short-lived romance, the two remained amicable after they broke up.
In 2006, Portman had another high-profile relationship with actor Jake Gyllenhaal. Although their relationship was brief, they stayed good friends. When presenting her with the "Desert Palm Achievement Award" in 2011, Gyllenhaal even teased about her being a vegan, which, he said, made picking restaurants a bit challenging when they were an item.
Kirsten Dunst: Tobey Maguire & Jake Gyllenhaal
Kirsten Dunst and Tobey Maguire’s love story began while filming the first Spider-Man movie. However, they broke up before the production of "Spider-Man 2" due to alleged salary disparities. Dunst revealed in an interview that the wage gap was significant. We love a queen who fights for her right to equal pay!
Her next relationship was with actor Jake Gyllenhaal, whom she met through her co-star in “Mona Lisa Smile,” Maggie Gyllenhaal. Despite her mother's objections, Dunst dated Gyllenhaal for almost two years and even lived with him in Hollywood Hills, sharing a pet German Shepard. Ultimately, their relationship ended due to radically differing lifestyles.
Emma Stone: Andrew Garfield & Dave McCary
Emma Stone met Andrew Garfield while filming “The Amazing Spider-Man” in 2011. Peter Parker and Gwen Stacy’s chemistry quickly led to a romantic relationship off-screen. While the couple often appeared together on the red carpet, they remained private about their relationship. In 2015, after four years of dating, they decided to take a break. Despite the split, the actors remained on good terms.
Stone’s dating life remained low-key until rumors surfaced in 2017 that she was dating Dave McCary, a writer and segment producer for "Saturday Night Live." They reportedly connected while working on the indie film “Brigsby Bear.” The pair announced their engagement in December 2019.
Sean ‘Diddy’ Combs: Cassie & Naomi Campbell
Diddy has six biological children with four different women. It’s safe to say his love life has been a wild ride, including his on-again-off-again relationship with Cassie Ventura (more commonly known as simply Cassie). Diddy and Ventura kept their relationship under wraps for years before finally going public in 2012. Rumors of a secret wedding started swirling in 2014, but the couple ultimately parted ways in 2018, reportedly due to Diddy's hesitation to settle down.
Years later, the rapper and Naomi Campbell started making headlines — and that wasn't even the first time! The two were first spotted together in 2001 after being photographed for British Vogue, sparking rumors of a romance that lasted for years. Neither confirmed their relationship publicly.
Sean Combs: Jennifer Lopez & Cameron Diaz
Few 90s pairings were as iconic as Sean Combs and Jennifer Lopez. These two superstars began dating in 1999 when JLo had just divorced her first husband, actor Ojani Noa. The power couple's romance hit a rough patch when they got into legal trouble after a violent nightclub altercation. They were even arrested, but somehow, it didn't hurt their careers.
Cameron Diaz and Diddy catch each other's eye in the midst of all the glitz and glamor of the 2008 Oscars. From then on, the press spotted them together numerous times. Eyewitnesses noted their playful flirting and even hand-holding! However, both stars have vehemently denied any romantic involvement. So, were they just "friends" or something more? We may never know.
Jude Law: Sienna Miller & Cameron Diaz
It was love at first sight for Sienna Miller and Jude Law, who first crossed paths on the set of “Alfie” in 2004. After a whirlwind romance, the couple got engaged on Christmas Day of the same year. Sadly, just months later, Law was caught getting intimate with his children's nanny, leaving Miller devastated. The couple reconciled but eventually split for good in 2011.
Although sources claim that Cameron Diaz and Jude Law bonded while working together, it remains unclear whether they were more than just friends. The two were seen going on late-night dinners together, and Law even introduced Diaz to his children, however, they never made a red-carpet appearance as a couple, suggesting that chemistry was strictly friendly.
Alex Rodriguez: Kate Hudson & Cameron Diaz
It was a sunny day in 2009 in Miami when Kate Hudson and "ARod" first locked eyes. Baseball sensation Rodriguez had just split from his wife. Hudson was fresh out of a relationship with Owen Wilson. Soon enough, the abundant PDA was proof that they were more than just friends. However, the romance faded after only seven months. In a later interview, Hudson hinted that it wasn't a serious relationship.
Not long after, ARod and Hollywood's sweetheart Cameron Diaz became an item. Their love story began at a lavish Miami pre-Super Bowl party in February 2010. They kept things low-key, but made some high-profile appearances together, causing a media frenzy. Sadly, they mysteriously decided to end things in June 2011.
Cameron Diaz: Justin Timberlake & Benji Madden
The early 2000s gave us unforgettable moments in pop culture and Hollywood couples. One of the most talked-about pairs of the time was Cameron Diaz and Justin Timberlake. Yup, Hollywood's sweetheart with the most sought-after member of N*Sync! Despite their nine-year age gap, their whirlwind romance took off and seemed serious, although they were both cautious about commitment. The couple stayed together for a solid four years before deciding to part ways.
Since then, Diaz has moved on and dated other high-profile celebrities. She married Benji Madden in 2015. In an interview, the actor said nothing else has mattered since she met Madden, and no one compares.
Jenna Dewan: Justin Timberlake & Channing Tatum
In 2002, Jenna Dewan became the subject of tabloid fodder when she briefly dated Justin Timberlake following his split from Britney Spears. Dewan was one of Timberlake's backup dancers at the time. But it wasn't until 2006 that she found true love when she met Channing Tatum on the set of “Step Up.”
The couple fell for each other and eventually got hitched in a magical ceremony in 2009. They then welcomed their little bundle of joy, Everly, in 2013. Sadly, the couple's love story ended in 2018 when they announced their separation on social media. Despite the breakup, the two remain committed to their roles as parents.
Adam Duritz: Jennifer Aniston & Courtney Cox
Before Jennifer Aniston married Brad Pitt and Justin Theroux, she dated Counting Crows singer Adam Duritz for a bit. The two met at Johnny Depp's exclusive nightclub in LA, the Viper Room, thanks to some sneaky friends who lied to both of them about having a crush on each other. Interestingly, Duritz didn't actually know much about the "Friends" star at the time, as he had been too busy touring.
A couple of years after their fling, Courteney Cox starred in the music video for Counting Crows's "A Long December" and hit it off with the band's lead vocalist! They pursued their feelings despite Duritz's previous relationship with Aniston. Details about their time together are shrouded in mystery.
Brad Pitt: Jennifer Aniston & Gwyneth Paltrow
Brad Pitt and Gwyneth Paltrow's whirlwind romance was the talk of Hollywood in the mid-'90s. Their love story began on the set of the movie "Seven" in 1994. The A-listers dated for two years before Pitt proposed. Shockingly, just six months later, the engagement was off. Pitt’s publicist reiterated that there wasn't any particular incident that led to the split.
In 1998, Pitt and Jennifer Aniston were introduced by their agents, and the rest was history. Bennifer's relationship quickly blossomed, culminating in a lavish Malibu wedding on July 29, 2000. Rumors later began to circulate that Pitt was getting too cozy with Angelina Jolie. While Pitt vehemently denied these allegations, the two announced their separation in January 2005.
Brad Pitt: Jill Schoeleon & Christina Applegate
Before Brad Pitt became one half of the infamous Brangelina duo, he had envisioned a future with Jill Schoeleon. The two actors met on the sets of “Cutting Class” and got engaged. After only three months, Schoeleon broke things off with Pitt for a movie director. Ouch!
Later, Pitt moved on to a brief but juicy fling with Christina Applegate. But the real kicker? Applegate and Pitt went to the 1989 MTV Video Music Awards together. Things took a turn when she ditched him halfway through the show for a mystery man. Actor Sebastian Bach later confirmed that it was him.
Sheryl Crow: Owen Wilson & Lance Armstrong
Sheryl Crow and Owen Wilson met while filming a not-so-well-known movie called "The Minus Man." Despite the eerie on-screen scenario, love was in the air! The couple dated for two years and even showed up all cuddly at the 2000 Vanity Fair Oscar party. Crow even dedicated a song, "Safe and Sound," to Wilson.
In 2003, Crow met Lance Armstrong and was reportedly smitten in an instant. The cyclist and the singer had a whirlwind two-year romance. He proposed in the middle of a lake during a romantic getaway in Idaho. Talk about a grand gesture! However, their love fizzled out just as quickly. No one knows why, but the couple split less than six months after that grand proposal.
Luke Wilson: Gwyneth Paltrow & Drew Barrymore
Back in the day, Gwyneth Paltrow was reportedly smitten with her co-star in “The Royal Tenenbaums,” the then-29-year-old actor Luke Wilson. As the film wrapped up, word on the street was that the lovebirds had rented a beach house in Pacific Palisades, California, for the summer. Neither of them confirmed nor denied those rumors, but they dated for a year before calling it quits.
Did you know that Drew Barrymore once dated Luke Wilson? She recently revealed that they were in an open relationship. The two stars bonded over their shared experiences in the industry, and their relationship quickly blossomed. While their time together was full of fun and adventure, Barrymore admits that neither of them took it too seriously.
Fabrizio Moretti: Drew Barrymore & Kristen Wiig
Drew Barrymore had a rock-solid five-year romance with The Strokes' drummer Fabrizio Moretti. It began backstage at a 2002 music festival and quickly blossomed into what Barrymore described as the most positive relationship she has ever had. Despite splitting up in 2007, Barrymore still holds a special place in her heart for Moretti and they're still close friends.
Kristen Wiig of "Bridesmaids" fame found love with Moretti in December 2011. She gushed about her beau in a 2012 interview, revealing that he had helped her find happiness, saying she was happier than she had ever been and felt very lucky. Sadly, after 18 months together, the couple reportedly called it quits. Impressively, the split was amicable and friendly.
Drew Barrymore: David Arquette & Christian Bale
Drew Barrymore and David Arquette first met when she was 16 and he was 20. They dated for a few months and went their separate ways. However, fate brought them back together in 1999, when they appeared as siblings in the romantic comedy, "Never Been Kissed." While Barrymore denied having gone out with Arquette, David confirmed that they had indeed dated, saying he tells it like it is.
In an interview with GQ Australia, actor Christian Bale shared a tidbit from his teenage years: he once went on one date with actress Drew Barrymore. According to Bale, they saw a terrible horror film, and the date didn't lead to anything further as Barrymore never called him again. Ouch!
Courtney Cox: Kevin Costner & David Arquette
Courteney Cox rose to fame in 1994 after landing the role of Monica Geller on the popular sitcom “Friends.” As her on-screen success skyrocketed, her off-screen dating life became just as fascinating. One of her rumored romances was with Kevin Costner, with whom she co-starred in "3000 Miles to Graceland."
However, her most high-profile relationship was with actor David Arquette. The two met on the set of “Scream” in 1996 and got married in 1999. Despite their marriage lasting more than a decade, the couple announced their separation in 2010. Cox has only had positive things to say about her relationship with Arquette post-divorce, calling him her best friend.
Joe Jonas: Demi Lovato & Sophie Turner
Joe Jonas and Demi Lovato met on the set of "Camp Rock" in 2010 and hit it off instantly. They even went on tour together! Things were going swimmingly until they suddenly announced they were just friends. Apparently, Jonas was the one to call it off. While they're no longer together, they've remained friends.
In 2016, a mutual friend brought Sophie Turner and Joe Jonas together and they hit it off instantly. In fact, Jonas popped the question after only a year of dating! Their surprise Las Vegas ceremony after the 2019 Billboard Music Awards was streamed on Instagram live, with watching fans beside themselves with excitement. In July 2020, they welcomed their daughter, Willa, into the world.
Gigi Hadid: Joe Jonas & Zayn Malik
For five magical months in 2015, Gigi Hadid and Joe Jonas were inseparable. Their friend, the fabulous Cara Delevingne, even captioned an Instagram photo of them with "Introducing G.I. Joe." The nickname stuck, and Hadid was later seen wearing a "G.I." tee on public outings. Their romance came to an end in November 2015.
Hadid and Zayn Malik were one of Hollywood's most famous on-again, off-again couples, with a six-year relationship that included Vogue photoshoots and the birth of their daughter Khai in 2020. However, their romance hit a rough patch when reports surfaced that Malik allegedly struck Hadid's mom during an argument, resulting in their breakup. The singer denied the allegations but pleaded no contest to the charges.
Kim Kardashian: Nick Cannon & Nick Lachey
Nick Cannon and Kim Kardashian were an item from late 2006 to early 2007. According to Cannon, it had to end because of a little thing called honesty. Cannon said if she had just come clean about the now-infamous tape debacle, they might still be together since the drama happened before they began dating.
98 Degrees member Nick Lachey also had a little thing with Kim K. During an interview on "Watch What Happens Live With Andy Cohen," he revealed that they went on one date in 2006 to see "The Da Vinci Code" and that calling her his "ex" would be a stretch. Lachey fondly called her a "nice girl" and shared that they don't keep in touch anymore.
Scott Disick: Kourtney Kardashian & Sofia Richie
Ready to take a ride on the emotional rollercoaster that is Kourtney Kardashian and Scott Disick's relationship? Through infidelity rumors and rocky breakups, Kourtney and Scott somehow weathered the storm and even welcomed three children into the world. Although they called it quits for good in 2015, these exes prove that co-parenting can be done with grace and respect.
When Disick began dating Sofia Richie, even her own father, Lionel Richie, dismissed their relationship. But the couple proved the skeptics wrong, living together and even enjoying holidays with the Kardashian clan and Disick's children. However, their romance came to an abrupt end in mid-2020. Disick later revealed that Richie wanted him to choose between her and his ex, Kourtney Kardashian.
Jacob Elordi: Kaia Gerber & Zendaya
Jacob Elordi and Zendaya's incredible chemistry on "Euphoria" fuelled speculation about whether their on-screen romance had spilled over into real life. While the rumor mill churned, the two never confirmed anything beyond their close friendship. Elordi has been spotted with several women since, while Zendaya has found herself in a web of romance with her Spider-Man co-star, Tom Holland.
Elordi and Kaia Gerber started dating back in September 2020, when they were first spotted on a date in Malibu. Interestingly, their romance came right after Gerber's fling with SNL's Pete Davidson. The couple was pretty darn good at keeping things under wraps. The few photos of each other they had on Instagram were deleted after their November 2021 breakup.
Cindy Crawford: Val Kilmer & Richard Gere
Cindy Crawford had a string of famous exes and made headlines in the early '90s, including a relationship with actor Val Kilmer. Kilmer later couldn't help but gush about his love for the supermodel in his memoir.
Crawford's most famous romance came in 1991 when she married actor Richard Gere. She was just 26 years old, while Gere was a seasoned 42. Despite seemingly having it all, the relationship was complicated. Crawford later revealed that their relationship was a lot of other things, but she didn’t know if they were ever friends or peers. She was a young model then, and he was “the” Richard Gere.
Madonna: Lenny Kravitz & Tupac
There was once a time when America was obsessed with Madonna's career and her romantic partners. One of her occasional music collaborators was Lenny Kravitz, and rumors had it that they were in a romantic relationship in 1990.
Madonna also dated the late rapper Tupac Shakur in 1993, after they were introduced by Rosie Perez at the Soul Train Awards. However, their relationship did not last, and Tupac reportedly ended things with Madonna in a letter while he was in prison in 1995. She has since moved on to other partners, famously marrying Guy Richie in 2000 and divorcing him in 2008.
Tom Cruise: Melissa Gilbert & Cher
You’ve heard of “TomKat” but did you know that Cruise dated Melissa Gilbert back in the day? Known for her role in “Little House on the Prairie,” Gilbert revealed that she and Cruise were an item before he was famous. It was so long ago that he was still going by his real name, Tom Mapother.
Fast forward years later, and Cruise meets none other than Cher! The two first met at Sean Penn and Madonna's wedding, a location infamous for celebrity romances. They ran into each other again at a casual event at the White House. While their relationship did not last, Cher considers Cruise one of her top five lovers!
Penelope Cruz: Matthew McConaughey & Tom Cruise
Penelope Cruz and Matthew McConaughey's on-screen chemistry in "Sahara" transcended beyond the movie set. However, their love story ended in 2006 when the couple announced they were taking some time off from their relationship. The official statement cited hectic work schedules as the reason for their separation.
A while later, Cruz began dating Tom Cruise, her co-star in "Vanilla Sky," effectively making them Cruz and Cruise. Their relationship began while Cruise was in the middle of his divorce from actor Nicole Kidman. Sadly, the pair parted ways in 2004, but sources claimed they remained on good terms and stayed friends.
Sandra Bullock: Ryan Gosling & Matthew McConaughey
One of Sandra Bullock’s most famous romances was with Ryan Gosling, whom she dated for about a year starting in 2002. The two met on the set of “Murder by Numbers” and quickly hit it off. Despite their 16-year age gap, Gosling later revealed that Bullock was one of the best girlfriends he had ever had.
Another of her high-profile relationships was with her "A Time to Kill" co-star, Matthew McConaughey. Although their relationship reportedly lasted for two years, neither of them publicly confirmed it at the time. Bullock tried to deny the rumors but eventually gave in and hinted that they had dated.
Eva Mendes: George Augusto & Ryan Gosling
From 2002 to 2011, actor Eva Mendes was in a relationship with George Augusto, a producer from Peru. During their nine-year relationship, Mendes was candid about her views on marriage, stating that she didn't see it as a necessary institution in modern society. Despite their long history together, the couple eventually went their separate ways.
In 2011, Mendes's love life took an unexpected turn when she met her current partner, actor Ryan Gosling, on the set of "The Place Beyond the Pines." They have since continued building an enduring relationship (sans the ring exchange, as she wished) and have two daughters.
Rachel McAdams: Ryan Gosling & Michael Sheen
While Rachel McAdams may not be one to flaunt her relationships in public, fans have been fortunate to catch a few glimpses over the years. One of these moments was when she won Best Kiss at the 2005 MTV Movie Awards with her co-star from “The Notebook,” Ryan Gosling. Their chemistry was undeniable. In an interview, McAdams shared that she often takes away a close relationship from every job she does — romantic or otherwise.
This was certainly the case when she met Michael Sheen on the set of “Midnight in Paris.” The two made their relationship official when they walked arm-in-arm at the 2011 Cannes Film Festival, but their romance was short-lived.
Michael Sheen: Kate Beckinsale & Sarah Silverman
Kate Beckinsale and Michael Sheen's love story began when they worked at a 1995 touring production of "The Seagull." A few years into their relationship, Beckinsale became pregnant with their daughter Lily. In 2002, the couple split, and shortly after, Beckinsale became engaged to director Len Wiseman. Although no longer together, they still hold respect and love for each other.
Prior to Sarah Silverman and Michael Sheen getting together, Silverman had dated Jimmy Kimmel, while Sheen had been linked to Rachel McAdams. In 2018, Silverman tweeted that she and Sheen had ended things. She clarified that there wasn't any drama involved, but the long-distance challenge was too much, with Sheen based in the UK and Silverman living in the US.
Eddie Fisher: Elizabeth Taylor & Debbie Reynolds
She was Hollywood's darling, and he was a rising star in the music industry. Debbie Reynolds and Eddie Fisher were the ultimate power couple. In 1955, they tied the knot, and the following year, they welcomed their daughter, Carrie Fisher. In 1958, their mutual friend, Mike Todd, passed away in a plane crash.
Fisher had allegedly been having an affair with none other than Todd's grieving widow, Elizabeth Taylor. By 1959, they went their separate ways, and Fisher wasted no time in marrying Elizabeth Taylor the same day his divorce from Reynolds was finalized. Taylor revealed that, in hindsight, marrying Fisher may have been more about finding comfort in the aftermath of Todd's death than true love.
Ryan Reynolds: Alanis Morissette & Kristen Johnston
Back in 2002, Alanis Morissette and Ryan Reynold’s love story reportedly started at Drew Barrymore's birthday bash. By June 2004, the pair was head over heels and engaged. Sadly, after a nearly three-year engagement, the couple announced their separation. Morissette's 2008 album, "Flavors of Entanglement," touched on the fallout of their relationship.
According to reports, Kristen Johnson had a brief relationship with Reynolds in the 1990s. In December 1999, the two were photographed attending the premiere of "The Green Mile" together. All signs pointed to a relationship, even though it may have been on and off. In a 2020 interview on "Watch What Happens Live," Johnston called her ex-flame a lovely person and recalled the relationship fondly.
Leonardo DiCaprio: Blake Lively & Rihanna
Leonardo DiCaprio has garnered a reputation not only for his impressive acting skills but also for his many flings and relationships. In 2011, the rumor mill about DiCaprio and actor Blake Lively made the rounds – reportedly, the two were involved in a short but intense romance during which they were seen together on a yacht in Cannes.
In 2016, DiCaprio's name was once again in the tabloids when he was spotted getting cozy with singer Rihanna at Coachella. Their rumored romance continued to spark speculation when they were spotted together in Paris and allegedly attended an after-party for Rihanna's birthday in 2017.
Rihanna: Travis Scott & A$AP Rocky
Singer and fashion icon Rihanna has had her fair share of rumored romances. One of her supposed flames was Travis Scott, whom she reportedly dated for about a year in 2015. Although neither musician confirmed the relationship, there were hints of a connection between them. Rihanna attended Scott's concerts, and he even contributed to her album "Anti" in 2016.
Rihanna has frequently been linked to A$AP Rocky as well. They collaborated on the track "Fashion Killa" in 2013 and worked together on Rihanna's Diamonds World Tour that same year. Since then, there have been several rumors about a possible romance, but it wasn't until May 2021 that A$AP Rocky publicly confirmed their relationship.
Ryan Philippe: Reese Witherspoon & Abbie Cornish
In the 1990s, Reese Witherspoon and Ryan Phillippe captured the hearts of fans after starring together in the film "Cruel Intentions." The duo fell in love and eventually tied the knot, welcoming two children, Ava and Deacon, into the world. Unfortunately, the marriage didn't last, and they officially divorced in 2008. The two are committed to successfully co-parenting their children.
Back in 2006, Phillippe and Abbie Cornish co-starred in "Stop-Loss," while he was still married to Witherspoon. When the two divorced, he and Cornish confirmed their relationship to the public, but gossip swirled about whether or not infidelity was at play. In 2008, Philippe spoke out against the media's portrayal of Cornish as a "homewrecker" and vehemently denied any infidelity.
Amanda Seyfried: Dominic Cooper & Ryan Philippe
Amanda Seyfried’s career isn't the only thing that's attracted attention over the years. Everyone’s interested in her love life. One of her most talked-about relationships was with "Mamma Mia" co-star Dominic Cooper who she dated from 2008 to 2009. Unfortunately, things didn't work out between them, and Amanda spoke candidly about the heartbreak she experienced after their split.
In 2011, Amanda briefly dated Ryan Phillippe, but their relationship was tumultuous. Seyfried admitted in an interview that the increased media scrutiny may have strained the relationship. We wonder if knowing that the media gets in the way of so many relationships will ever make it less nosey. Sadly, we don't think it will.
Kristen Stewart: Stella Maxwell & Dylan Meyer
Kristen Stewart and model Stella Maxwell had a rocky relationship, with multiple breakups and makeups throughout their time together. While the couple was often out and about, Maxwell opted not to share their relationship on her social media accounts. The two eventually called it quits for good in August 2019.
Since then, Stewart has been very open about her current relationship with fiancée Dylan Meyer. The usually private actor has been more than happy to share her affection for Meyer with the world. In a November 2019 interview on "The Howard Stern Show," Stewart spoke candidly about her chemistry with Meyer, describing it as "sick."
Robert Pattinson : Kristen Stewart & FKA Twigs
While Robert Pattinson prefers keeping his personal life private, one of his most publicized relationships was with Kristen Stewart, his co-star in the Twilight films. The two began dating in 2009 but kept their relationship out of the public eye until photos surfaced of Stewart kissing her director on the set of another movie. The couple split soon after.
Pattinson also dated singer FKA Twigs. The press first spotted them hanging out with friends in NYC in 2014. The couple went public with their relationship a month later and got engaged in 2015. However, they eventually decided to split up after two years together.
Milas Kunis: Macaulay Culkin & Ashton Kutcher
The world knew little about a young Mila Kunis’s dating history until the year 2002 when the word got out that she was in a relationship with fellow child star Macaulay Culkin. Despite being a private couple, rumors of their engagement began soon after they confirmed their relationship. Their love story was one for the books, but unfortunately, the fairytale ending wasn't meant to be.
Long after her split with Culkin, Mila crossed paths with Ashton Kutcher at the 2012 Golden Globe Awards. Ashton invited her to a house party, and they hit it off. The pair tied the knot and have two children.
Salma Hayek : Edward Norton & Francois-Henri Pinault
Salma Hayek has been turning heads for decades since her breakout role in "From Dusk Till Dawn" (1996). Hayek has had some epic romances, including one with actor Edward Norton. The two met thanks to their chiropractor and frequently appeared together at events and games. Despite the public appearances, they managed to keep their relationship under wraps until they split in 2003.
In 2006, Salma moved on to a new beau — François-Henri Pinault, chairman and CEO of Kering, which owns some of the world’s most luxurious brands. On Valentine's Day in 2009, the couple made it official with a quiet ceremony in Paris.
Drake: Zsa & Tyra Banks
Canadian rapper Drake has become known for his romantic exploits, often referencing his relationships in his music. Case in point, the rapper has claimed that he and musician Zsa had dated. Another name on Drake's dating list is Tyra Banks.
Granted, "dated" might be overstating things. Apparently, it was just one date, and he wasn't even sure about the nature of it — romantic or otherwise. He revealed on The Ellen DeGeneres Show in 2013 that they went on a single date to Disneyland. Drake clarified that he wasn't sure if it was a date or just a get-together, but he enjoyed the experience, and they remain close friends.
Janet Jackson: Jermaine Dupri & Wissam Al Mana
Janet Jackson and Jermaine Dupri were once the quintessential hip-hop power couple. The two reportedly met backstage at one of her concerts in 2002 and hit it off. Although they served up serious #couplegoals, their love story ended in 2009.
As Jackson got older, she decided to switch things up in her dating life. She met her third husband, businessman Wissam Al Mana, at a hotel opening in Dubai. The couple kept their relationship low-key and secretly tied the knot in 2012. Their son, Eissa Al Mana, was born in January 2017, but the couple parted ways just three months after his birth.
Brooke Shields: Andre Agassi & Chris Henchy
Brooke Shields has had several celebrity suitors, but her relationship with tennis pro Andre Agassi is probably the most well-known. The couple met in 1993, and their courtship was anything but ordinary as they communicated primarily through lengthy faxes! They married in 1997 but filed for divorce after two years. Shields was deeply unhappy since Agassi was dealing with substance dependency and had started alienating her.
After her divorce, Shields found love with Chris Henchy, a supervising producer on the show "Spin City." In 2001, they tied the knot in a secret ceremony in Marina del Rey and are still going strong.
Matt Damon: Minnie Driver & Winona Ryder
Matt Damon has had his fair share of high-profile relationships over the years. Perhaps the most talked-about of these was his romance with Minnie Driver, his co-star in "Good Will Hunting." In true Hollywood fashion, their relationship began on set but ended in a messy breakup that made headlines in the late 1990s.
During an appearance on "The Oprah Winfrey Show," Damon announced that he was "single," blindsiding Driver, who learned she was newly single from the show. Damon soon began dating Winona Ryder. While Damon and Ryder's relationship was short-lived, she had only good things to say about him.
Alexis Bledel : Jared Padlecki & Milo Ventimiglia
Alexis Bledel gained a dedicated following for playing the book-loving Rory Gilmore in "Gilmore Girls." Her on-screen chemistry with co-star Jared Padalecki, who played her character's first love interest Dean, sparked rumors of a real-life romance. However, it wasn't until the release of the show's revival that the press confirmed what fans had known all along — the two had dated.
Bledel also found love with Milo Ventimiglia, who played Rory's on-and-off again boyfriend, Jess. The couple reportedly began dating in 2003 after meeting on set and even discussed the possibility of marriage at one point. They called it quits in June 2006 after nearly four years together.
Sarah Jessica Parker: Michael J. Fox & Robert Downey Jr.
Hollywood's biggest stars, Sarah Jessica Parker (of "Sex and the City" fame) and Michael J. Fox (of "Back to the Future" fame) were an item in the 1980s. The relationship reportedly lasted for a year, and although there were many photos of the couple together, there were rumors that their romance was a PR stunt.
After her split from Fox, Parker dated Robert Downey Jr. for nearly seven years. However, their relationship came to an end due to Downey's struggles with substance abuse. In a candid interview, the "Iron Man" star admitted that his dependency was a major factor in their relationship ending.
Leighton Meester: Sebastian Stan & Adam Brody
Leighton Meester and Sebastian Stan (that's before he became Bucky Barnes in the MCU) first crossed paths in 2007 on the set of the CW hit drama series “Gossip Girl.” The media began speculating about a romance between Meester and Stan in early 2008. The two reportedly went their separate ways in the spring of 2010.
Meester found love again with fellow teen television icon Adam Brody, who starred in the popular series “The OC.” The couple first met at Canter's deli in Los Angeles and went on to tie the knot in 2014. They are still going strong and have two children.
Margot Robbie: Alexander Skarsgard & Tom Ackerley
Australian actor Margot Robbie has been the subject of various rumors surrounding her dating life. One was about her alleged affair with her co-star Alexander Skarsgard while filming “The Legend of Tarzan.” Sources claimed the two were "inseparable" and had a strong physical connection. However, Robbie's most significant relationship to date has been with her now-husband, Tom Ackerley.
The couple met on the sets of "Suite Française" in 2014, where Ackerley worked as an assistant director. They started dating shortly after and surprised everyone with a secret wedding in 2016. Despite their celebrity status, the couple has chosen to keep their relationship private.
Daniel Craig : Rachel Weisz & Heike Makatsch
Daniel Craig and Rachel Weisz are a couple who tend to keep their personal lives out of the spotlight. Rachel explained that privacy is paramount to protecting your marriage. They've been together since 2011 so she must have a point. Before finding love with Weisz, Craig dated several other high-profile women.
One of Daniel's past flames was Heike Makatsch, the German actress who played the conniving office worker Mia in the beloved holiday film “Love Actually.” The two were an item for seven years before calling it quits on amicable terms. According to Craig, their busy work schedules often kept them apart for long periods.
Alison Brie: David Sullivan & Dave Franco
It might come as a surprise to some fans, but Alison had a two-year relationship with David Sullivan, who was her first celebrity beau. This information may have flown under the radar since social media, especially Instagram, wasn't as prevalent back then. Additionally, Alison and David were still making a name for themselves in the industry. Their romance reportedly ended in January 2010.
In 2017, Alison tied the knot with actor Dave Franco in a hush-hush ceremony. Since then, the couple has become more open about their relationship and frequently showcases their love on social media for their fans to gawk at.
Meryl Streep: John Cazale & Don Gummer
Despite her enduring fame, Meryl Streep has managed to maintain a relatively private personal life. She met her first celebrity love interest John Cazale while working together on a New York stage production, and the two became romantically involved. Unfortunately, their love story was cut short when Cazale died from lung cancer only two years later.
Six months after Cazale's untimely death, Streep found love again with sculptor Don Gummer, whom she married in 1978. The two have three daughters and one son. Although Gummer occasionally accompanies his wife to Hollywood events, the couple keeps the details of their relationship private.
Kerry Washington: David Moscow & Nnamdi Asomugha
Kerry Washington, known for her role as crisis management leader Olivia Pope in "Scandal," has kept her personal life under wraps, much like her on-screen character. We know she dated actor David Moscow for four years before ending their engagement when she turned 30 to focus on herself. Moscow is best known for his role as the younger Tom Hanks in the movie "Big."
Washington's romantic life took a turn when she met former Oakland Raiders player Nnamdi Asomugha in 2009 while performing in a production of "Race." The pair hit it off and have been inseparable ever since. The couple tied the knot in a secret ceremony in Hailey, Idaho, in June 2013.
Lili Reinhart: Cole Sprouse & Spencer Neville
The chemistry between "Riverdale" stars Lili Reinhart and Cole Sprouse spilled into real life, much to the delight of their fans. The actors dated for almost three years before ending things in March 2020. Sprouse confirmed the split in an Instagram post a few months later. Reinhart has since identified herself as a proud bisexual woman and seems to be exploring new romantic possibilities.
In April 2022, she walked arm in arm with actor Spencer Neville at Coachella. While it's unclear whether there's anything more than a friendship between the two, it hasn’t stopped the rumors of a potential romance.
Amy Schumer: Anthony Jeselnik & Dolph Ziggler
Amy Schumer has made waves in the industry with her standup routines and feminist sketches on "Inside Amy Schumer." During a 2012 appearance on "The Howard Stern Show," Schumer opened up about her dating history and revealed that she had dated fellow comedian Anthony Jeselnik. Despite the potential for a fantastic comedic match, Schumer explained that she ended things because Jeselnik was not attentive enough.
She also dated WWE wrestler Dolph Ziggler but ultimately ended things with him, admitting that she even broke up with him over text. While Schumer may have moved on, it seems Ziggler may have taken the breakup harder than she thought.
Isla Fisher : Darren Day & Sacha Baren Cohen
Isla Fisher first rose to fame as the star of the Australian soap opera “Home And Away.” She met actor and singer Darren Day during their performance in the stage show adaptation of the 1960s Cliff Richard film, “Summer Holiday.” Their relationship soon bloomed, and they began planning for an autumn wedding. Things didn’t pan out, and the couple split after two years.
Fisher’s love life took a different turn when she met comedian Sacha Baron Cohen in 2002 at a party in Sydney, Australia. The couple hit it off and tied the knot in a beautiful Jewish ceremony in Paris in March 2010. Since then, the happy pair have welcomed three children into their family.
Jennifer Lawrence: Nichola Hoult & Chris Martin
Jennifer Lawrence has a reputation for being a little quirky, but she's generally kept her romantic life private, sometimes allowing occasional glimpses. After meeting on the sets of “X-Men: First Class” in 2010, she and Nicholas Hoult began dating. They broke up for good in 2014 while filming “X-Men: Days of Future Past.”
After her breakup with Hoult, Lawrence, and Coldplay frontman Chris Martin became an item in 2014. Given that Chris was still in the process of divorcing Gwyneth Paltrow, fans were surprised by the unlikely pairing. The pair seemed unfazed by the scrutiny. They remained together until officially breaking up in 2015.
Phoebe Waller-Bride: Conor Woodman & Martin McDonagh
Phoebe Waller-Bridge and Conor Woodman have an intriguing story about how they met. Woodman saw Waller-Bridge in a play where she had to strip down as part of the role. He was so taken with her performance that he tracked her down on Facebook to ask her out on a date. She agreed, saying it was easier because he had already seen so much of her.
After dating for a while, the couple got married in 2014. They announced their separation in late 2017. As for her relationship status today, Waller-Bridge has been seeing filmmaker Martin McDonagh for years but has remained tight-lipped about it.
Richie Sambora: Heather Locklear & Denise Richards
Before Heather Locklear found her current partner Chris Heisser, she was married to Richie Sambora, Bon Jovi's lead guitarist. They were introduced by mutual friends and were engaged seven months later. After her previous relationship with the notorious bad boy Tommy Lee, Locklear said she found solace in Sambora's gentle soul. Their marriage impressively lasted from 1994 to 2007.
Sambora started dating actress Denise Richards in 2006, shortly after his divorce from Locklear. Their romance caused a stir since Richards was previously friends with Locklear. Sadly, their love story was short-lived due to personal challenges: Sambora's father was diagnosed with lung cancer, and Richards was in a custody battle with her ex-husband, Charlie Sheen, while also supporting her ill mother.
Ian Somerhalder: Nina Dobrev & Nikki Reed
Ian Somerhalder and Nina Dobrev not only played the iconic couple of Damon Salvatore and Elena Gilbert on "The Vampire Diaries" but also dated off-screen for three years. Dobrev initially had no intention of dating her co-star, but sometimes love has a way of sneaking up on you. Although they split in 2013, they remained friends and continued to work together professionally.
Can you believe Nikki Reed and Ian Somerhalder got engaged just six months after they started dating? And that wasn't even the end of it — they tied the knot just a few months later, in April 2015. Over the years, the couple has welcomed a beautiful daughter named Bodhi Soleil, and their bond has only grown stronger.
Ariana Grande: Pete Davidson & Big Sean
From their lovely duets to their red-carpet appearances, Ariana Grande and Big Sean's love was clear. However, their demanding schedules made it hard for them to spend quality time together. After 8.5 months of dating, the two decided to part ways but have remained supportive of each other.
Grande and comedian Pete Davidson fell head over heels for each other in the spring of 2018. Davidson proposed within weeks of dating! Sadly, just four months later, the couple ended things. What made this split even more heartbreaking was the tragic loss of Grande's ex-boyfriend, Mac Miller, who passed away just a month before. In a candid confession, Davidson admitted that he knew the tragedy marked the end of their relationship.
Josh Hutcherson: Vanessa Hudgens & Victoria Justice
Fresh from her split with Zac Efron, Vanessa Hudgens starred in the adventure movie, "Journey 2: The Mysterious Island" (2010). On that movie set, she became smitten with her charming co-star, Josh Hutcherson. The two kept their romance hush-hush during filming. Interestingly, it was only when they broke up (less than a year later) that they confirmed they ever were together.
One of Victoria Justice’s relationships came hot on the heels of her hit show "Zoey 101." The duo was pretty tight-lipped about their relationship. Sure, they were spotted together on and off red carpets, but they never officially confirmed their dating status. That being said, there are plenty of photos and insider scoops suggesting they were a thing.
Alex Pettyfer: Emma Roberts & Diana Agron
Alex Pettyfer and Emma Roberts started dating in 2008 after meeting on the set of "Wild Child." Their relationship was highly publicized, and Pettyfer even got a tattoo of Roberts' initials on his finger. Despite their year-long romance coming to an end, Pettyfer doesn't regret getting the tattoo.
"Glee" star Diana Agron and Pettyfer first met on the set of their action film "I am Number Four," but it was when he visited her on the set of “Glee” that he won her over. Though they never confirmed their relationship, sources say they were smitten with each other. Apparently, Agron ended things a year later after the press released incriminating photos of Pettyfer with models Lydia Hearst and Leven Rambin.
Johnny Cash: Vivian Liberto & June Carter
Johnny Cash and Vivian Liberto's love story began in 1951 at a roller rink when Cash was 18 and Liberto was 17. They got married in 1954, and their first child, Roseanne, was born nine months later. However, after 13 years of marriage, they divorced, with Liberto blaming Cash's substance problem and relationship with June Carter for the split.
Johnny Cash and June Carter’s journey began backstage at an Elvis concert in 1956. Although they were both married at the time, Cash pursued her relentlessly and she eventually reciprocated his feelings. She famously described their connection as being "in a ring of fire." In 1968, they finally tied the knot. They remained devoted to one another till the end.
Courtney Love: Kurt Cobain & Billy Corgan
Courtney Love had first seen Kurt Cobain at his concert a year before they officially met. They finally came face to face by chance at a Seattle nightclub in early 1990. They quickly became an item and got married in Hawaii on February 1992. The unconventional wedding had Cobain sporting his pajamas and Love donning a white lacey satin gown. Unfortunately, their love story was cut short when Cobain passed away in 1994.
Billy Corgan and Courtney Love were romantically involved before her relationship with Cobain. The couple supported each other's musical aspirations and had a deep connection before fame took over. According to Corgan, they were both struggling artists at the time, trying to achieve a common artistic goal.
Jack Nicholson: Anjelica Huston & Rebecca Broussard
Anjelica Huston and Jack Nicholson had a complex relationship spanning several decades, although they never tied the knot. Their romance started with a bang in 1973 when they met at Nicholson's birthday party. The chemistry was palpable and they soon began dating. Sadly, constantly competing for Nicholson's attention was becoming too much and their relationship came to an end in 1990.
Rebecca Broussard and Jack Nicholson crossed paths thanks to a mutual friend. They began dating right away despite Nicholson's relationship with Huston at the time. They eventually moved in together and had two children. They hit a rocky patch, and they eventually split after five years together. Rebecca gained custody of their children.
Aaron Carter: Hilary Duff & Lindsay Lohan
Aaron Carter revealed that he started dating Hilary Duff on his 13th birthday. A year and a half later, he started showing interest in Lindsay Lohan. Some speculated that Duff's 2002 song "Haters" was inspired by this situation. Though they lost touch after breaking up, Duff expressed her kind condolences on Instagram after Carter passed away in 2022.
The talk about Carter dating both actresses simultaneously allegedly caused tension between the ladies. Despite the drama, Lohan stated in a 2003 interview that she harbored no ill will towards either Carter or Duff. On receiving the news of Carter’s untimely death, Lohan said that there is a lot of love there, and her heart goes out to Carter and his family.
Billy Bob Thornton: Laura Dern & Angelina Jolie
In the late 1990s, Laura Dern and Billy Bob Thornton were romantically involved, and they even got engaged. Their love story started when they appeared together on an episode of the sitcom "Ellen." However, the engagement never led to marriage. While she was away filming a movie, Dern learned that Thornton had married Angelina Jolie. She later revealed it felt like experiencing a sudden death.
Jolie and Thornton's marriage was definitely unique, notorious for wearing vials of each other's blood as necklaces. The couple first met on the set of "Pushing Tin" in 1999 and tied the knot in 2000, but their marriage only lasted until 2003. Thornton has shared that he looks back on their time together fondly.
Marilyn Manson: Dita Von Teese & Evan Rachel Wood
Dita Von Teese and Marilyn Manson began dating in the early 2000s. They eventually tied the knot in 2005, with a private ceremony in Los Angeles followed by a grander celebration a week later. However, Von Teese filed for divorce on December 29, 2006, leaving their home in a rush on Christmas Eve.
Evan Rachel Wood and Marilyn Manson were romantically involved from 2006 to 2010 and even got engaged at one point. However, in a candid 2021 Instagram post, Wood publicly revealed that Manson was mistreating her. Tired of living in fear, Wood bravely decided to expose Manson, as well as his enablers. Manson has consistently denied any wrongdoing, despite several other women coming forward with similar allegations.