Most celebs want to be known for their skill, but it often depends on who you’re dating and when you’re dating them. The media is thrown into a frenzy when two great stars get together. Every glimpse and photo of the couple is eagerly anticipated throughout the world. The “Hollywood Curse,” on the other hand, ensures that relationships in the City of Dreams do not last. But if these celebrities believe that we would forget about their previous relationships, they are incorrect. We’ll now refresh your memory with some of the most well-known superstar partnerships from the past that you might have forgotten about.
Lennie Kravitz and Nicole Kidman
Nicole Kidman and her musician husband, Keith Urban, are known for their PDA. Kidman was previously engaged to singer Lenny Kravitz, long before Keith and even Tom Cruise.
The former couple got engaged in 2003, but the Stepford Wives star later explained that she “wasn’t ready” to marry, thus the couple never married. Nicole Kidman, on the other hand, has gone on to feature in the smash series Big Little Lies alongside Kravitz’s daughter, Zoe.
Sandra Bullock and Matthew McConaughey
Sandra Bullock and Matthew McConaughey began dating after appearing together in the film A Time to Kill. It’s difficult to recall a period when McConaughey wasn’t married to Camilla Alves, and the couple was admired for their wonderful romance as well as their stunning beauty.
However, four years before they married, McConaughey told Playboy about his affair with Bullock, saying, “She’s not a little girl. She’s a lady. She could rule a country,” he continued to say of his then-girlfriend.
Ryan Reynolds and Alanis Morissette
On their separate social media profiles, Ryan Reynolds and his current wife, Blake Lively, have demonstrated they are “couple goals.” The Deadpool actor dated Alanis Morissette before discovering the Gossip Girl star, marrying her, and having two children with her.
The Canadian actor and the Canadian singer first met in 2002 and dated for four years. Reynolds had indeed proposed to the “Ironic” singer, but the pair never exchanged vows. Instead, they split up in 2006.
Reese Witherspoon and Jake Gyllenhaal
When Reese Witherspoon’s marriage to Ryan Philippe, the father of her children, fell apart, it was a difficult moment for her. Fans, on the other hand, were overjoyed when it was revealed that Witherspoon had begun dating the incredibly attractive Jake Gyllenhaal.
When the two superstars met on the set of the film Rendition in 2007, flames flew. They married soon after, but their relationship only lasted two years, as the Big Little Lies star and the Brokeback Mountain actor split up in 2009.
Mila Kunis and Macaulay Culkin
Mila Kunis dated Macaulay Culkin, the star of Home Alone, while she was on That ’70s Show. The pair started dating in 2002 and stayed together for eight years.
“He was big,” Kunis said in an interview with Howard Stern. “You couldn’t go on a walk with him down the street. He’s always had this strange allure, as if fans shouted when they saw him!” Since they called it quits in 2011, it appears that the attraction between the two was no longer there.
Gisele Bundchen and Leonardo DiCaprio
We’re still waiting to see which woman can sweep Leonardo DiCaprio off his feet, despite the fact that he’s one of the world’s most renowned bachelors. It’s difficult to say because he formerly dated Gisele Bundchen, the world’s highest-paid supermodel.
Gisele dated Leo on and off for over six years before marrying Tom Brady, a prominent football player. They formed a lovely couple, but it was not to last. Perhaps Leo will follow in the footsteps of George Clooney and marry in his fifties.
Blake Lively and Penn Badgley
Although we previously stated that Ryan Reynolds and Blake Lively were ideal “relationship goals,” the world was once pulling for Blake Lively and her co-star, Penn Badgley.
They were not only co-stars on Gossip Girl, but they were also each other’s love interests. Fans of Gossip Girl delighted at the announcement, as they had gone from an on-screen romance to an off-screen one. The couple broke up in 2010 after three years of dating, but happily, they reunited on Gossip Girl.
Bradley Cooper and Renee Zellweger
Bradley Cooper is on every girl’s mind, yet he hasn’t been in a relationship since 2015. He dated actress Renée Zellweger before encountering his current girlfriend and mother of his kid, Irina Shayk.
They met on the set of the 2006 thriller Case 39, but started dating after the film’s release in 2009. After months of silence in the media about their relationship’s state, the pair refused to speak about it, opting instead to make public appearances together. The former couple announced their quits in 2011.
Lindsay Lohan And Samantha Ronson
Lindsay Lohan dated Hard Rock Cafe heir Harry Morton in 2006 after her romance with That ’70s Show actor Wilmer Valderrama ended. Following their split, the star of The Parent Trap was linked to Samantha Ronson, a British DJ.
The actress and the singer began dating in 2008, but their high-profile engagement ended in 2009. Lohan told Us Weekly that she and her girlfriend were not meant to be together because “two toxic people cannot be together.”
Angelina Jolie and Jonny Lee Miller
Angelina Jolie has earned her fair share of stories in the media as a result of her relationship choices, not to mention her controversies and indiscretions.
Jolie was married to Jonny Lee Miller before her high-profile marriage to Brad Pitt, her Mr & Mrs Smith co-star. The former couple began dating of their film, Hackers, in 1995, just like her and Pitt. A year later, in March 1996, they married, but three years later, in 1999, they divorced.
Michael Keaton and Courtney Cox
Courtney Cox is most known for her part as Monica Geller on the classic sitcom Friends, although she was dating Michael Keaton before becoming one of the most popular and highest-paid actresses for this role.
In fact, before parting up in 1995, Keaton and Cox dated for nearly six years. She married David Arquette a year later, barely one year after her initial appearance as a prominent character on the NBC sitcom. They have one child together, however they are no longer married.
Sarah Jessica Parker and Robert Downey Jr.
Sarah Jessica Parker is full of praise for her present husband, Matthew Broderick, although she did have another meaningful relationship before meeting her soulmate.
In fact, before their breakup in 1991, the Sex and the City actress dated fellow actor Robert Downey Jr. The couple was together for seven years before calling it quits, and the actor’s difficulties with addiction at the time were the catalyst for their breakup.
Kim Kardashian and Nick Cannon
Kim Kardashian is now married to Kanye West, a rapper and musician, and the world is following her and her family’s every move. Kim was attempting to stay up with Nick Cannon before we were all watching Keeping Up with the Kardashians.
The couple started dating in September 2006, before Kim Kardashian became one of the world’s most famous women, but the relationship barely lasted four months. In January 2007, the couple called it quits, and Cannon went on to marry and divorce Mariah Carey.
Michelle Rodriguez and Zac Efron
When Michelle Rodriguez and Zac Efron were rumored to be dating, everyone thought they were an improbable couple. Rodriquez is ten years older than the High School Musical star, so their romance was unexpected.
They proved everyone wrong by dating for only two months before ending their relationship on a “very mutual” basis. Perhaps it had something to do with the fact that Rodriguez began dating model Cara Delevingne the same year.
Kate Bosworth and Orlando Bloom
Most females drool over Orlando Bloom anytime he appears on television, but some lucky ladies have had the chance to date the Pirates of the Caribbean star.
While he is most known for marrying Miranda Kerr, a gorgeous Victoria’s Secret model, in 2010, he was previously married to Kate Bosworth. The Blue Crush actress had a two-year relationship with the beautiful actor before calling it quits in 2005. Kate, on the other hand, is just another example of Orlando’s penchant for attractive women.
Ben Affleck and Gwyneth Paltrow
Gwyneth Paltrow seems to have been into leading Hollywood guys before marrying a popular British singer. While her relationship with Brad Pitt did not work out, she did date Ben Affleck, the actor from the film Good Will Hunting.
The celebrity couple began dating in 1997 and dated for two years till 1999, then temporarily reuniting before calling it quits in 2000. Paltrow told Howard Stern, “He’s incredibly clever, really, really talented, and he’s amusing. However, he wasn’t in a position in his life where he needed a partner.”
Mark Ronson and Rashida Jones
Mark Ronson is known for creating singles like Bruno Mars’ “Uptown Funk” and Amy Winehouse’s “Valerie,” so it’s no wonder Rashida Jones was once smitten with him.
From 2002 until 2004, Ronson and Jones dated and were even engaged at one time. After a year together, Ronson proposed to the actress by making a crossword puzzle with the inscription “Will you marry me?” Their engagement lasted a year and was called off along with their relationship.
Usher and Rozonda “Chilli” Thomas
Usher and Rozonda “Chilli” Thomas were both prominent celebrities in the early 2000s because of their musical careers, but they became a power couple when they started dating.
The singers started dating in 2001, and Rozonda even appeared in Usher’s “U Got It Bad” music video that year. However, the couple was claimed to have split up in 2003 due to Usher’s adultery, despite the TLC singer saying, “I suppose it was that time or something.”
Justin Timberlake and Jenna Dewan-Tatum
Jenna Dewan may have been in one of Hollywood’s most famous marriages before splitting from her ten-year spouse, Channing Tatum, but she was linked to Justin Timberlake before she even met her ex-husband.
Jenna was a backup dancer for Justin Timberlake’s “Cry Me a River” vocalist in 2002, which was also the end of Timberlake’s romance with Britney Spears. Jenna told Andy Cohen, “We dated…yeah. We were buddies who later started dating….I wasn’t the rebound!”
Brad Pitt and Shalane McCall
This isn’t the first time Brad Pitt has been on this list, and it won’t be the last. But, given his ‘ladies man’ image, that shouldn’t come as much of a surprise. In the mean time, you might be more likely to have forgotten who Shalane McCall.
In any event, he’s shown with Shalane McCall, a (now) former child actress and model best remembered for her role as Charlotte “Charlie” Wade on CBS’s prime-time serial opera Dallas. Pitt scored a four-episode stint on Dallas when he was 24 years old, when he met 15-year-old McCall and began an eyebrow-raising connection with her.
Tyra Banks and Seal
Seal’s high-profile marriage to model Heidi Klum is certain to be remembered by many. However, the singer had another top supermodel before meeting the German beauty.
Seal has a fondness for models, as seen by his brief relationship with Tyra Banks in 1996. While Tyra Banks hasn’t had much luck with love after their brief affair, Seal married Heidi Klum in 2005, and their marriage lasted nine years before they divorced in 2014.
Scarlett Johansson and Jack Antonoff
Jack Antonoff dated Scarlett Johanson before he began dating Girls actress Lena Dunham. In reality, when they were 17 and in high school, the two actors dated for two years.
Furthermore, in 2002, the adolescent sweethearts attended prom together. For the exes, things are drastically different now days, and while Antonoff’s romance with Lena recently ended, Scarlett has been married twice and divorced. In 2011, she divorced Ryan Reynolds, and just last year, she divorced Romain Dauriac after three years of marriage.
Michael Cera and Aubrey Plaza
In 2010, Michael Cera began dating Aubrey Plaza, his Scott Pilgrim vs. the World co-star. The stars dated for nearly a year before breaking up, but Plaza subsequently spoke up to Vulture about their relationship.
“After we shot that movie, we travelled across the nation and almost got married in Vegas,” she remembered. Aubrey began seeing Jeff Baena a year later, and the two have been together ever since, so Michael Cera appears to be out of the picture.
Sandra Bullock and Ryan Gosling
Sandra Bullock was believed to be dating Ryan Reynolds in 2011, but this would not be the first Ryan in her life. In reality, in 2002, the Miss Congeniality actress had a one-year relationship with fellow actor Ryan Gosling.
Not just because they were both prominent stars in Hollywood, but also because their romance became public after they met on the set of Murder By Numbers. Instead, it was their 16-year age disparity that drew the media’s attention.
Dennis Rodman and Madonna
Madonna had a high-profile romance with filmmaker Guy Ritchie, and when their marriage ended in 2008, their divorce was even more public. But there was Dennis Rodman before Ritchie.
In 1994, the singer of “Papa Don’t Preach” dated the basketball star for a short time. This was after his divorce from Annie Bakes, and since then, the former basketball player has married and divorced twice more.
Jared Leto and Cameron Diaz
From 1999 until 2003, actress Cameron Diaz dated 30 Seconds To Mars frontman Jared Leto. The previous pair was even supposed to be engaged around this period, with Diaz allegedly wearing a $15,000 engagement ring to the Golden Globes in 2003.
However, it appears that the pair was moving in the opposite direction that same year, and they have since gone their separate ways. Before marrying Benji Madden, Diaz had a succession of romances, and Leto is still single.
Kate Hudson and Alex Rodriguez
Alex Rodriguez has dated Jennifer Lopez since 2007, and has been connected to Cameron Diaz and Madonna. However, there was a point when the baseball player dated Kate Hudson, the actress from the film How to Lose a Guy in 10 Days.
In 2009, the celebrity couple dated for seven months before calling it quits. It had only been a year since his divorce from Cynthia Scurtis, his six-year wife, was finalized. During their marriage, A-Rod and Cynthia had two kids together.
Lamar Odom and Taraji P. Henson
Apart from his high-profile connection with Khloe Kardashian, it’s difficult to recall who else Lamar Odom was romantically associated with. While the marriage did not endure, it continues to be a topic of discussion in the media owing to the basketball player’s regrettable acts.
Odom, on the other hand, was linked to actress Taraji P. Henson in the past, and she even invited him to a Golden Globes party in 2009. Odom was said to have proposed to Henson in 2009, just weeks before tying the knot with Khloe.
Wilmer Valderrama and Mandy Moore
Wilmer Valderrama has had a number of high-profile romances, including one with Lindsay Lohan and another with Demi Lovato more recently. However, between 2001 and 2002, the actor from That ’70s Show dated Mandy Moore, the actress and singer from This Is Us.
Moore went on to date Scrubs star Zach Braff in 2004, before marrying her long-term partner, Ryan Adams, in 2009. Wilmer is still single after the couple’s divorce.
Tom Cruise and Cher
After telling Andy Cohen that Tom Cruise, the star of Top Gun, was in her “top 5,” Cher may wish she could go back in time. Meanwhile, the duo only dated for a short time in 1985, and it was simply a fling, so many people may have forgotten about them.
Cher’s 1970s marriage to Sonny Bono was more well-known, while Cruise’s romances and marriages to Nicole Kidman and Katie Holmes were more public than his time with Cher.
Nick Jonas and Selena Gomez
It’s difficult to keep track of who Selena Gomez is seeing these days: is it Justin Bieber, The Weeknd, or Justin Bieber all over again? Meanwhile, prior to her relationships with any of the singers, Gomez dated fellow Disney actor and boyband member Nick Jonas.
During this period, the Jonas Brothers released “Burnin Up,” which went on to become their first top five success in the United States, and Gomez starred in the music video for the song.
Justin Timberlake and Alyssa Milano
While Jenna Dewan-Tatum stated that she was not Justin Timberlake’s rebound after his heartbreaking break-up with Britney Spears, Alyssa Milano claimed that she was.
“Right after Britney shattered his heart, I swooped in for the kill!” the Charmed actress claimed years later about her brief relationship with Justin Timberlake in the early 2000s. Justin Timberlake went on to have a long-term romance with Cameron Diaz before marrying Jessica Biel after the two failed to establish a meaningful connection.
Julie Bowen and David Spade
E! News referred to David Spade as “a bachelor-era George Clooney of the comedy industry,” and there’s a good reason for it.
While in the public spotlight, the humorous actor, who rose to popularity on Saturday Night Live, has had a succession of leading Hollywood ladies, but he has failed to settle down with any of them. Julie Bowen, the actress from Modern Family, is among the ladies on this list. When Spade was on Just Shoot Me! and Bowen was on Ed, the two dated for a year in 2002.
Danny Boyle and Rosario Dawson
On multiple occasions in 2013, Rosario Dawson and Danny Boyle were seen looking more than buddies. When reports began to circulate that the putative couple had broken up, Rosario spoke to NET-A-PORTER about it.
“It’s not like we proclaimed our romance, so it’s not like we’re going to announce our split,” she told the outlet. Meanwhile, the images spoke for themselves, with the filmmaker and actress spending time alone together and seemed closer than friends.
Keira Knightley and Jamie Dornan
He now has the lucrative part of Mr. Christian Grey on screen, but he had already attracted the eye of British actress Keira Knightley before he was cast in the film adaptation of the best-selling novel.
The lovely couple started dating in 2003 after meeting while filming an ad campaign, but split up in 2005. Both performers were relatively unknown at the time, but have since gone on to international fame, with Keira starring in the famous Pirates of the Caribbean franchise.
50 Cent and Chelsea Handler
50 Cent and Chelsea Handler are maybe one of the most surprising pairs on our list. Even though she declared in an Oprah interview that “I’m not going to date somebody whose name is a number,” the comic talk-show presenter dated the famous rapper in 2010.
Nonetheless, it appears that this man, whose stage name is a number, swept the blonde beauty off her feet, and throughout their time together, she felt “satiated.” Any relationship between the two, on the other hand, was doomed to fail.
Seth MacFarlane and Emilia Clarke
Seth MacFarlane created the successful animated sitcom Family Guy, and Emilia Clarke portrays Khaleesi, Mother of Dragons, in HBO’s Game of Thrones, and their paths intersected in 2012.
However, the surprising couple called it quits in 2013 after only six months of dating. Meanwhile, Clarke was named the most attractive woman in the world by AskMen readers a year later, as well as Esquire’s Sexiest Woman Alive in 2015, so Seth appears to have lost out big time.
Scarlett Johansson and Sean Penn
Scarlett Johansson and Sean Penn made news in 2011 when they made their romance public. Their affair sparked outrage owing to their significant age gap, with Penn being 50 at the time and the Lost in Translation actress being only 26.
After five months together, however, allegations surfaced that Sean Penn “did not want to be tied down” to Scarlett and therefore ended their relationship. According to further sources, Johansson attempted but failed to reignite the romance between the two.
Simon Cowell and Carmen Electra
Music mogul Simon Cowell dated former Playboy model Carmen Electra for a brief period in December 2012 to February 2013. Electra stated about her ex-boyfriend Simon Cowell that he is “amazing and really lovely.”
When it was revealed that Cowell had not remained faithful and was the reason for their breakup, he was not so fantastic. “I simply thought Simon was so much fun and was so brilliant and he’s incredibly intriguing,” Carmen stated.
Brad Pitt and Christina Applegate
When Christina Applegate, star of Married… With Children, took Brad Pitt as her date to the 1989 MTV Video Music Awards, everyone assumed the two were dating.
We can’t blame Christina for falling for Brad Pitt, who has subsequently become one of the most gorgeous guys on the planet. However, the blonde stunner dumped her up-and-coming actor date for another man halfway through the night! Sebastian Bach, a Skid Row musician, claims to be the person, though Christina has never verified.
Jake Gyllenhaal and Kirsten Dunst
Kirsten Dunst was the “It Girl” of the moment after her role in the successful picture Spiderman in 2002. As a result, it’s no surprise that hunk Jake Gyllenhaal had his sights set on the actress.
The renowned actors married in 2002 and divorced two years later in 2004. While their hearts broke throughout this time, so did the hearts of all their followers when the breakup was confirmed. Dunst told Allure in 2009, “It would be lovely to meet him, but we’re not good friends.”
Ashton Kutcher and January Jones
It’s difficult to forget that Ashton Kutcher was formerly married to actress Demi Moore, and that he is now married to Mila Kunis, a former co-star.
Do you recall when Kutcher was dating January Jones, the star of Mad Men? Let us refresh your mind in case you forgot. Before both of his high-profile romances, the famous actor dated the blonde bombshell for three years, ending their relationship in 2001. Jones began dating Josh Groban two years later and dated him for the following three years.
Owen Wilson and Sheryl Crow
Sheryl Crow was notoriously engaged to Lance Armstrong, however she dated Owen Wilson from 1999 to 2001 before Lance. “I’ve always dated successful men, which would appear to place me on par with them,” she adds.
“However, what happens is that one of you shrinks – and it’s always been me. I believe that in order for one person’s light to shine, everyone else’s light must be dimmed.”
Chris Evans and Jessica Biel
Jessica Biel is well-known for her marriage to Justin Timberlake, with whom she shares a kid. Biel, like her renowned musician husband, had a number of high-profile and long-term romances before to marrying him.
The Sinner star began dating fellow actor Chris Evans during her last years on 7th Heaven. The pair started dating in 2001 and dated on and off till June 2006. Biel met Timberlake when her relationship fell apart, and the rest is history!
Pink and Joey Fatone
Although they were not in a high-profile relationship, no one can deny that Pink dated a member of N’SYNC back in the early 2000s. Any female would have been blessed to be on the arm of one of the guys when N’SYNC was the biggest boy band in the world.
She told Glamour, “He took me on a date to Friendly’s and bought me an ice cream. Such a darling, he sought my father’s approval!”
Mariah Carey and Luis Miguel
“I haven’t had that many, but there has been a variety pack,” Mariah Carey said in a recent interview with Cosmopolitan magazine on the men in her life. I’ve only ever been with five individuals in my life, so I’m a prude in comparison to most others in the business,” she says.
That gives each of her relationships greater weight, not least the one she had with Luis Miguel, the Latin vocalist she dated from 1998 to 2001.
Nick Lachey and Kim Kardashian
The former member of the boyband 98 Degrees and 90s star may not have dated Kardashian for long, but it still qualifies in our book. “It’s a bit of a stretch to call her my ex,” says the author.
When Kim got up to use the toilet halfway through the movie, Nick was astonished to discover 25 photographers standing outside. Nick only had kind things to say about the reality star, despite their brief relationship history.
George Clooney and Lucy Liu
George Clooney was once regarded as one of Hollywood’s most desirable bachelors before the arrival of his now-wife Amal. He dated a number of stunning and well-known women, including Lucy Liu from Charlie’s Angels.
Although it was never verified, the couple was frequently photographed together around the year 2000. The allegations were almost verified when photographers caught the two kissing in the back of a limousine in classic Hollywood couple style on New Year’s Eve.
Janet Jackson and Matthew McConaughey
During a game of “Plead the Fifth” on the late-night talk program Watch What Happens Live, presenter Andy Cohen attempted to clear the air on the long-running rumor that McConaughey dated Janet Jackson.
McConaughey’s initial response was to giggle and try to avoid the topic, but when Cohen persisted, he ultimately admitted that he had dated the singer… but only for a short time. “We went out to eat. I guess that was it,” he said.
Brooke Shields and Nicolas Cage
Brooke Shields was once regarded as one of Hollywood’s most divisive “it” ladies in the 1980s. So it’s no surprise that she’d hook up with Nicolas Cage, a bad boy who has a reputation of dating some of Hollywood’s most gorgeous ladies (and ending each relationship disastrously).
The specifics of their relationship are unknown, but when Cage invited Shields to the opening of his film Moonstruck, it became clear that it was more than a flirtation.