Some good things are just not meant to last, and some romances are just not meant to end with wedding bells. Nonetheless, the stories of our favorite celebrity couples stay with us for decades. Who could ever forget about Angelina Jolie and Brad Pitt or Justin Timberlake and Britney Spears? However, with all the new couples making us gush and squeal, and all the long-time partners breaking our hearts with all the splitting up happening here and there, we have forgotten some of the celebrity duos we have made investments on in the past. Don’t you worry, because we’ve got you covered! We’ve compiled a list of some of the Hollywood couples you’ve probably forgotten. Let’s revisit their beginnings and how they made us swoon, as well as how they ended and made our hearts ache. Grab some popcorn – and maybe some tissues – as we go down memory lane and take a look back at some of the entertainment industry’s forgotten duos.
Who knows, you might even be surprised to know who once dated who!
1. Bradley Cooper and Renée Zellweger
Bradley Cooper and Renée Zellweger are undoubtedly two of the biggest names in the industry. Each one has the credit of owning quite an impressive portfolio filled with unforgettable roles in hit movies, as well as a long list of praises and awards. However, it seems their popularity may have overshadowed their romance.
In 2006, the two stars met in the production of the supernatural horror film Case 39. The couple chose to remain private about their relationship, and not much is known in the in-between. What we do know is that in 2011, the two decided to go on their separate ways. Right now, they seem to be on good terms. The two met again at the 92nd Academy Awards, and it seemed they were enjoying each other’s company. They may not have ended up with each other, but it seems they did get their happily ever after – just not in the way others expected!
2. Angelina Jolie and Jonny Lee Miller
We all know about Angelina Jolie and Brad Pitt, but before there was Angelia and Brad, there was Angelina and John Lee Miller. The two met while filming the crime film Hackers in 1995. In a way, you could say they were head over heels for each other as they immediately got married in 1996. It was definitely not an ordinary wedding to any degree. The two only had a few guests – two, to be exact, the actress’ mother and one of Miller’s friends. The actress undoubtedly would have looked amazing in the traditional white dress, but Jolie didn’t stick to the norm. She rocked her wedding by wearing black rubber pants and a T-shirt with Miller’s name written on it. However, in 1999, the two decided to go their separate ways, but they seem to be on very good terms and have remained friends.
3. Justin Timberlake and Jenna Dewan-Tatum
Jenna Dewan is best linked to Channing Tatum, and for good reason as the two were married for around a decade! However, before Tatum swept her off of her feet, Dewan was first the backup dancer of Justin Timberlake. Later on, Dewan and Timberlake would date, a romance that immediately started in the middle of the talked-about break-up of the Cry Me a River singer with Britney Spears.
Not much is known about the romance that happened with the two, especially since it seems Dewan just recently confirmed that they did have a relationship in 2002. However, we know that it was short-lived, and they seemed to have found new people soon after. In the end, there seems to be no bad blood, and they’ve just learned to put their investments in different people. Let’s be happy for them for finding love!
4. Alexis Bledel and Milo Ventimiglia
Were you a big fan of comedy-drama Gilmore Girls? If so, then you probably know Rory Gilmore and her love interest Jess Mariano! The roles go to none other than Alexis Bledel and Milo Ventimiglia. To fans’ delight, the on-screen duo also became a couple off-screen. The two stars got together soon after Ventimiglia first appeared on the show in 2001. However, they ended things in 2006, and it totally crushed a lot of fans. Do you know what’s more heartbreaking? Bledel shared that they had even discussed marriage before. They were so close! The couple never explained why their relationship ended, but it seems they’re on good terms and have no problem working together! Let’s give the two some credit for being great sports. Right now, they’re taking different paths in life. Here’s to a better future for the both of them!
5. Jared Leto and Cameron Diaz
Do you remember Jared Leto and Cameron Diaz? The former is an American actor and musician. He has been in hit films such as Fight Club and Girl, Interrupted. On the flip side, Diaz is a retired actress. However, she is also a model, author, and producer. The two are undoubtedly amazing, and prominent in the industry. They’re so famous that some people have even forgotten that at one point, they have dated. In 1999, the two stars officially started dating. Since their relationship seems to have been forgotten by the industry, it would be easy to imagine that they only had a short-lived romance, but no! The former couple put their investments in each other for around four years. After going their own ways, the two have found other people to share their lives with. Leto is currently dating Valery Kaufman, while Diaz is married to Benji Madden.
6. Cameron Diaz and Alex Rodriguez
Cameron Diaz truly does put her heart on the line when she loves. In 2010, she dated Alex Rodriguez, and they were together for six years! They were one of the most private couples in Hollywood, to the extent of avoiding each other at a party. Their relationship was only confirmed a month before they decided to go their separate ways. They reunited after this initial split, but ultimately their relationship ended after a few months. Despite all that happened between them, we should give them credit! The stars decided to call it quits because they both wanted to focus on their careers. Now, that’s what we call dedication. With that said, the two are on good terms and are even friends. Reportedly, Rodriguez even went as far as saying that Diaz one of the greatest human beings he has ever met. Awww!
7. Cameron Diaz and Justin Timberlake
Cameron Diaz and Justin Timberlake were both linked with many other stars, and maybe that’s partly the reason some fans believed the two would have ended up together. The two stars have just really nailed the “for worst” part down with all the problems they’ve faced in Hollywood. Don’t even get us started on that tabloid issue. While the stars separated a long time ago, they were together for almost four years!
The two first met in 2003 and ended things in 2007. They never really explained what happened and why they decided to go their separate ways, but we do know that they seem to be on good terms now. They have not only worked once but twice after the split. If there’s any bad blood, it seems you wouldn’t see any hint of it anymore. The two have now put their investments in different people. Timberlake is married to Jessica Biel, while Diaz is married to Benji Madden.
8. Scarlett Johansson and Jack Antonoff
Long before we knew her as Black Widow, Scarlett Johansson’s dated musician Jack Antonoff, a music producer who is also known for the indie acts Bleachers and Fun. The surprising couple’s unsuccessful relationship started in high school, specifically, New York City’s Professional Children’s School. According to reports, Johansson and Antonoff began dating in 2001 and went to prom together.
The couple split up shortly after graduation because Johansson got caught up in her career. Antonoff released a song a few years after their breakup that pretty much verified his love story. He wrote Better Love, which features some lyrics with the actress’ name on it. Despite any scars they may have, they have done well in the decade since their separation. Antonoff went on to become a guitarist and drummer. In 2014, he went solo with Bleachers and has songwriting credits for artists like Lorde and Taylor Swift. On the other hand, Johansson became one of Hollywood’s A-listers and is currently married to the comedian Colin Jost.
9. January Jones and Josh Groban
Josh Groban rose to prominence in the 2000s after releasing four multi-platinum albums. The singer’s first passion was acting, but his career path changed after he stood in for Andrea Bocelli alongside Celine Dion. He already earned his degree of fame in the music scene and earned double-platinum under his belt when he started dating January Jones. She was working on the cinematic diamond American Wedding at the time their love blossomed. They were both in their early twenties — he was 22, and she was 25. The pair did appear on the red carpet regularly, even though their relationship didn’t make the daily tabloids. In June 2006, they declared they were taking a break and that they intended to remain friends. After that, the story vanished from the front pages. The two seem to be in somewhat different circles at the moment; he is still making his music while she continues to pursue her acting career.
10. Julia Roberts and Liam Neeson
Since his modest beginnings as an actor in the late 1970s, Liam Neeson has starred in a slew of critically acclaimed films, even earning him an Oscar nomination for his performance on Schindler’s List. It turns out that, aside from being a phenomenal star, Neeson was also a total heartthrob when he was younger.
The action star has dated Julia Roberts after appearing together in the 1987 film Satisfaction. She was 19 at that time, and he was already a well-known actor. The couple lived together within two weeks of their first meeting, saying that he was her first leading man—the couple dated for over a year before breaking up in 1988. Roberts became an icon in Hollywood and has been married to Daniel Moder for over two decades now. On the other hand, Neeson cemented his reputation as a blockbuster star with acting credits in the Taken trilogy.
11. Julia Roberts and Lyle Lovett
Julia Roberts and Lyle Lovett had a romantic relationship that ended almost as quickly as it had begun. Even though both Roberts and Lovett appeared in Robert Altman’s 1992 film The Player, the actress has stated that she and Lovett met through mutual friends.
They were friends at first but found solace with each other after their previous relationships ended. Roberts and Lovett shocked the media-consuming community when they married in a small Indiana town after a three-week whirlwind romance. Although their friends and colleagues were suspicious of their relationship, Roberts was head over heels in love with Lovett. Unfortunately, their partnership began to face several difficulties from that point on. It was difficult for the couple to find time for one another, mainly after Roberts left to finish her film The Pelican Brief. After less than two years, Roberts and Lovett legalized their separation with the help of their lawyers. The ex-lovers are both happily married to other people, and it appears that they have moved on from each other.
12. Kate Hudson and Alex Rodriguez
We’re guessing you either forgot about K-Rod or had no idea they existed until now. Kate Hudson met Alex Rodriguez in November 2008 at the reopening of the Fontainebleau Hotel in Miami. The baseball player had split from his wife Cynthia Scurtis and started dating Madonna that year. On the other hand, Hudson had recently broken up with former on and off boyfriend Owen Wilson. Her regular presence at his games eventually confirmed the status of their relationship at that time.
She was then dubbed A-good Rod’s luck charm after he won the World Series while dating her. However, after just a few months together, the two decided to part ways. After their split, Hudson has had several film and television appearances as well as several lifestyle investments. Speaking of Rodriguez, he retired from baseball in 2016 and dated Jennifer Lopez.
13. Kid Rock and Pamela Anderson
Pamela Anderson’s marriage to Kid Rock was short, which surprised the singer, who had hoped for a long-term relationship. Kid Rock has been entertaining people for over 30 years with his popular songs like The Polyfuze Method and Devil Without a Cause. On the other hand, Anderson’s racy modeling photos and appearances on shows like Baywatch, Home Improvement, and V.I.P. have made her famous over the years.
The model and actress met her former husband at the VH1 Divas gig. A year later, Kid Rock proposed, but they called off the engagement in 2003. The relationship seemed to be over for good, but we were wrong. The pair got married at a romantic ceremony on a yacht in Saint-Tropez in July 2006. They both thought they’d be together for the rest of their lives. Unfortunately, forever was just four months long. The two have since moved on with their lives.
14. Lenny Kravitz and Nicole Kidman
Lenny Kravitz and Nicole Kidman became a thing in the early 2000s, but only a few people can recall it. They were very private, and most people didn’t expect them to date. Kidman is a refined actress destined for Hollywood success, while Kravitz is a bohemian rock star with eccentric fashion preferences. Despite their many conflicts, the two clearly connected and cared deeply for each other.
Kidman and Kravitz met while he was her landlord. In either case, their relationship began in 2002. They were a power couple: she was dazzling fans with film investments, while he rocked the music scene with a slew of Grammys. Their relationship was so private that even their closest friends were unaware that they were engaged. Unfortunately, their relationship did not last and they called it quits after a year. According to them, they weren’t ready, and it wasn’t right. They are now on friendly terms, but a source close to the rock star claims that the actress is “the one who got away” and that she is his true love.
15. Michael Keaton and Courteney Cox
Courteney Cox, best recognized for her role as Monica Geller on the hit television show Friends, got her first acting opportunity in Dancing in the Dark. From there, it was all uphill for the actress, who went on to star in the hit series Family Ties. The actress is known to be formerly married to David Arquette, but did you know that she had been with Michael Keaton for over five and a half years?
The specifics are unknown because they kept their love lives a secret, but reports claim they had their first date at Cox’s home. They always prioritized their privacy during their dating period. Instead of dining out at lavish and flashy restaurants, the couple enjoyed home-cooked meals. They were a match made in heaven, with similar sensibilities on every stage. However, the lovely pair split up in 1995, before they could reach the six-year mark of their relationship. The two went on to build a degree of their own in their respective careers.
16. Natalie Portman and Moby
Natalie Portman is a versatile actress who has been acting since she was a child. She had a degree in Harvard in addition to her acting accomplishments. In comparison, Moby is familiar to almost everyone on the planet with his cult singles Porcelain, Extreme Ways, and A$AP. He has also arranged the soundtracks for cult films.
Moby detailed his relationship with Portman in a published excerpt from his memoir Then It Fell Apart, recounting how he met the actress backstage at a concert in Austin, Texas. However, there was one flaw: the actress denied some of it. She also pointed out some basic factual mistakes in his novel, such as the fact that she was not 20, as he said in the excerpt, but had only recently turned 18. Portman confirmed a portion of Moby’s story, claiming that they met after a show and that they hung out as friends a handful of times. She soon learned he was an older man and decided to stop seeing him.
17. Kim Kardashian and Nick Cannon
For Nick Cannon, there was Kim Kardashian before Mariah Carey. He and the reality star began dating in September 2006, but it is unclear how they met. Kardashian was still relatively unknown in the entertainment industry at the time, but she appeared in the press due to her affiliation with other celebrities.
Fans often saw the pair out and about with Hilton and other celebrity pals such as Lil’ Kim. During one of those appearances, Cannon also claimed credit for introducing Kardashian and Kanye West. Their relationship lasted a few months before they allegedly broke up in January 2007, just before Keeping Up With the Kardashians blew up and catapulted her into stardom. Following his breakup with Kardashian, Cannon embarked on perhaps his most high-profile relationship to date when he married Carey. Kardashian, on the other hand, married West in 2014.
18. Nick Lachey and Kim Kardashian
When one thinks about Nick Lachey’s romantic past, Jessica Simpson is likely to come to mind. However, it’s important to note that the 98 Degrees frontman once dated a relatively unknown Kim Kardashian. However, Lachey refused to refer to the reality star as his “ex.”
Lachey was caught on cam with Kardashian after his separation from his first wife, Jessica Simpson. In a 2013 interview, he mentioned their 2006 date, saying that they went to see a cinema and encountered 30 photographers waiting for them outside the theatre. Despite having a lovely time, the reality TV star did not contact him again. He has not heard from her since. It’s all good as they have both moved on with their lives. Lachey is currently married to Vanessa Minnillo, with whom he shares three children. Kardashian, on the other hand, built her empire along with her husband Kanye West and their four kids.
19. Pink and Joey Fatone
Joey Fatone and Pink once went on a date. According to Pink, the NSYNC member “is a sweetheart.” In the early 2000s, they had a special bond. Fatone was still a member of NSYNC at the time, while Pink was amassing an incredible degree of fame with hits like There You Go and Lady Marmalade.
Pink revealed her relationship history to Glamour in 2013, and the fling became public. She talked about the singer, saying, “Joey Fatone was in love with me.” The NSYNC member has admitted that he and the hitmaker went out a few times several years ago and that while he was smitten with Pink, she didn’t feel the same way. Fatone and Pink found love with other people after that. Fatone is married to Kelly Baldwin, and the couple shares two daughters. Meanwhile, Pink has been married to Carey Hart, a former professional motorcycle racer, since 2006.
20. Sarah Jessica Parker and Robert Downey Jr.
Well, it was years ago, but Carrie Bradshaw and Tony Stark were once a power couple. Sarah Jessica Parker had not yet established herself as a star on Sex and the City when she met Robert Downey Jr.
The two met on the set of the film Firstborn in 1984, and their relationship was adorable from the start. They were so smitten that they moved in together eight weeks after their first date. Although they were both in the spotlight, Downey Jr. clarified that his partnership with Parker aided both of their careers. When we thought they were becoming serious about each other, the couple’s fairy-tale relationship ended after about seven years together. Both actors moved on to prove their career investments in Hollywood. Despite the difficulties and heartache she experienced during her eight years with the actor, SJP claims she has no regrets.
21. Sandra Bullock and Matthew McConaughey
The days of Sandra Bullock and Matthew McConaughey’s dating are long gone, but it’s good to recall the partnerships that once existed. Long after they split up, Bullock said the sweetest thing about McConaughey, demonstrating how close they are now.
Before his happily married bliss with Camila Alves, McConaughey dated some other prominent women, including Bullock. In 1996, the stars’ relationship blossomed on the set of A Time to Kill. This film catapulted McConaughey to a degree of fame, and it turns out Bullock was instrumental in landing him in the role. After she was successful in getting him cast in the film, they dated for about two years. On the other hand, they were not quick to reveal details about it, preferring to be less open about what was going on in their personal lives. Bullock said she feels “really cared about” by her ex-boyfriend, which was the sweetest thing she said about him. Bullock also said that she is confident that they will always “keep close,” demonstrating the strength of their bond.
22. Ryan Gosling and Sandra Bullock
Sandra Bullock’s involvement with fellow actor Ryan Gosling is one Hollywood relationship we all seem to have forgotten. Even though the two did not last, they were among the most talked-about couples of the early 2000s.
The two met while filming Murder By Numbers, a film in which they both starred in 2002. However, this was not your usual case of an on-screen pair being an off-screen couple. Bullock portrayed a cop on the hunt for a young rich man, played by Gosling. This story isn’t necessarily a romantic recipe. However, the two grew intimate and made their first public appearance as a couple in September 2001. The pair’s 16-year age difference drew a lot of attention at the time, so they kept their relationship under wraps. Like most Hollywood breakups, they sealed their fate in the pressures of show business. Although they were a cute couple, it seems that their relationship was only supposed to last as long as it did. They have both married and started families and investments of their own.
23. Jennifer Garner and Scott Foley
Jennifer Garner and Scott Foley was once an item. Yes, you’ve read that right. They were actually together and most people intend to forget about it since Garner’s marriage to Ben Affleck was more popular. Garner and Foley were both young when they got married, but both of them poured out every investment they could to make their relationship last. Unfortunately, some things are bound to break.
Garner admitted that she had some regrets marrying while she was under 30. She also had some negative things to say about Foley and how their union was a huge mistake, but this was all before they found new peace and a civil relationship. They met pre-fame, and both admitted that they were in over their heads at the time. They tied the knot in 2000 but eventually called it quits in 2003. They announced their breakup publicly, with Garner saying that they never had a fair shot. The actress became too famous.
24. Sheryl Crow and Owen Wilson
Sheryl Crow and Owen Wilson was a pair we often forget about, that is because we can’t see these two hooking up. They have different personalities and what other sources would refer to as with very less chemistry. They met while filming Wilson’s movie and Crow took a minor role, credits to the initial hello’s and first impressions, the two automatically decided to go out and they started dating from then on.
They have been in a serious and committed relationship for two years, but their love story didn’t go past that point. Crow has a lot of accolades in the music industry. In fact, she is making headlines with her songs, but it turns out that it wasn’t just her music which made headlines but her love life too. Crow, at the time, had been engaged three times but never made it down the aisle. She had a long list of high-profile former boyfriends like Eric Clapton, Lance Armstrong, and more.
25. Matt Damon and Winona Ryder
This is a pair which we wouldn’t expect to have happened. Even today, we still twist our heads every time someone reminds us that Matt Damon and Winona Ryder were actually in a romantic relationship at one point in time. These two talented actors didn’t have as much investment with each other as they had with other people. Damon chose to marry someone who wasn’t an actor, while Ryder has been in a relationship with Scott Mackinlay Hahn since 2011.
However, these two still had a great time together. It turns out that after a long list of high-profile former lovers, Ryder was the last star who Damon dated. The actor later admitted that even during the time he was dating the actress, he already had second thoughts in his mind since he only really wanted to date non-celebrities form that moment on. Their relationship didn’t last a year, but they remain good friends even to this day.
26. Michelle Rodriguez and Zac Efron
This may be the least expected celebrities to get together, but Michelle Rodriguez and Zac Efron were once together.may be far apart in age, but. Like most celebrity summer romances, theirs didn’t last very long, even though Efron admitted that he had a lot of investments on the actress. Rodriguez, on the other hand, said that she couldn’t handle the actor’s commitment and that he was too serious for her.
The actress is open to dating both men and women. Perhaps her most controversial relationship was with supermodel Cara Delevingne. The actress revealed that she couldn’t make it past 6 months with someone. She also admitted that she feels like she wasn’t even born yet, and she may have accomplished a lot but she doesn’t want to be committed to anyone, let alone have kids, because by then she would regret not doing all the things she wants to do with her youth. Rodriguez calls herself a lone wolf.
27. Ashton Kutcher and January Jones
Ashton Kutcher and January Jones were a couple from the 90’s, which we all have seemed to forget. Most of the younger people today haven’t even heard about them. People are obsessed about Kutcher’s love story with his wife, the actress Mila Kunis. Clearly the two are always meant to be since they are soul mates, but we still can’t get enough of the fact that Kutcher and Jones dated in the past.
Kutcher is not up for giving credits to his former lover Jones. The actress was a supermodel back then and hadn’t gotten her famous role on Mad Men and broken into the film industry yet. They have since moved on with their lives. Kutcher is now an investor and happily married to Kunis, with whom he shares two children. Jones is a single mother who last appeared in the Netflix drama Spinning Out.
28. Michelle Rodriguez and Cara Delevingne
Michelle Rodriguez’s most famous relationship or what she would like to refer to as a fling, was with supermodel Cara Delevingne. Credits to their matching strong personalities, these two actually have one of the best couple chemistries of all time. As Rodriguez mentioned in all of her interviews, she can’t stand the thought of committing to someone for good. The actress added that she is the type to remain very private about her personal life, but she gets caught on cameras since she is always being watched in every place she goes to.
Rodriguez added that she never cared about anyone else’s opinion, because if she did, she would have been more careful about her moves. Delevingne was said to be in love with the actress but unfortunately they had a turbulent relationship. The two called it quits and the supermodel eventually moved on with actress Ashley Benson, but these two will remain as one of our most favorite couples.
29. Jake Gyllenhaal and Kirsten Dunst
Jake Gyllenhaal and Kirsten Dunst are a memorable pair. We have to give credits to these two for having a decent breakup after everything they’ve been through. The two met in 2003, thanks to the actor’s sister Maggie who introduced them. They started dating the very same year. They called it quits in 2004 for a lot of reasons. For one, their relationship was very much widely publicized. It created memes all over the media, including one of Dunst eating a salad with her fingers looking very tired and the actor was staring at his former girlfriend disgusted and unimpressed. There was also one serious rumor which stated that these two allegedly displayed serious PDA. Sources confirmed that these were all just stories made up by people considering that both actors were at the peak of their careers when they got together. They were 23 and 24 at the time, Dunst said it was never going to work since the actor is a homebody and she is an outdoorsy girl.
30. Lamar Odom and Taraji P. Henson
Lamar Odom once dated Taraji P. Henson before he married Khoe Kardashian. The athlete said his regrets are huge. He recalled that the actress had so much of her commitment, investments, and love poured into their relationship. He referred to his younger self as an immature punk.
Odom and Henson were a couple we can now only see together in our dreams. They were once so perfect for each other. The extremely beautiful actress deserved better as sources said, but still, Odom will forever be a part of her growth especially when it comes to the lessons she’s learned. During their relationship, the basketball player admitted that he fell in love with Kardashian. He married her 30 days after they met. Today, he still tells stories about how Henson cared for him so deeply and intensely. She was more mature than him, not just by age but by mentality too. He said she gave him inspiration, as a woman with color who works like that.
31. Madonna and Dennis Rodman
We are not sure if we could ever forget about these two getting together. Madonna and Dennis Rodman will forever be one of the most controversial couples of all time, credits to both of their fame and success in each of their fields.
It all started in 1994, when Rodman was one of the brightest stars when it comes to the sports of basketball. Madonna was already the queen of pop, and so she has decided to have her crush invited over to her mansion. Rodman received the invitation and as he got there, dozens of people were waiting in the lawn, the garden, and the backyard with cameras and setting up for a photo shoot. The diva came out and they had an instant public display of affection even before they were able to speak to one another. All of the pictures were kept by Madonna. They dated for two months. Rodman recently revealed that Madonna was willing to pay him $20 million to have his child.
32. Tom Cruise and Penelope Cruz
People always say that Penelope Cruz dodged a bullet when she decided to break it off with legendary actor Tom Cruise. These two had a lot in common than just the sound of their last names. They are both hard workers and great actors; they also make good investments both in businesses and production.
They were together for 3 years. Fans couldn’t get enough of this pair as they first announced their relationship. People around the world shipped them, but then suddenly, Cruise allegedly had conditions about certain beliefs and rules that the actress must follow if they ever were to take their relationship to the next level. He told the world how the actress reminded him of the elegance and beauty of Audrey Hepburn and with that, we cannot argue. The two remain very private about the real reason why they broke up, but they are still friends. The actress found her true love after the split with Javier Bardem.
33. Mariah Carey and Luis Miguel
Mariah Carey and Luis Miguel had a very steamy and PDA filled relationship for three years. Considering that they are both Latin Hispanic, they can’t get enough of each other’s natural sexiness and appeal. From 1993, they can’t seem to get enough of one another, credits to their burning love and chemistry.
Carey was in the middle of her legal separation with former husband when the two started dating. As she looks back on her relationship with Miguel, she doesn’t regret a single thing. She even said that she can’t contain how grateful she is for the times they spent together loving each other. She said they have stayed good friends and that Miguel actually helped her get through a very hard stage in her life. It wasn’t in a form of healing, it was something else. It is such a shame why these two called it quits since they seemed perfect for each other. Ultimately, the legendary singer realized that Miguel was not the one.
34. Orlando Bloom and Kate Bosworth
Orlando Bloom and Kate Bosworth dated in 2002, but unfortunately, their romance ended in 2005. Their love story is perhaps one of the most heartbreaking stories we have had with us during our childhood. Bloom was a heartthrob, credits to his role as Legolas in the Lord of the Rings franchise. During the peak of his fame, he announced to all the ladies in the world who were falling in love with him that a certain lady has already won his heart. Just as all hearts were healed and fans turned their sadness in to rooting for these two, they announced that they decided to split up.
They were even engaged at one point. Bosworth was the first serious relationship Bloom had in Hollywood. They were young but they were so in love. After their breakup, it changed the actress’ life forever and it also made her vow never to date actors again. There was something in her relationship with Bloom which made her promise to herself that she can’t be involved with a celebrity romantically. It served as a wakeup call.
35. Wilmer Valderrama and Mandy Moore
Wilmer Valderrama and Mandy Moore had a very interesting relationship. They were basically kids since they first met when the singer and actress was just fifteen. They met again when she was 16. With their paths crossing constantly, Valderrama didn’t hesitate the second time around. He took a chance and asked the singer out.
Moore was one of the brightest stars in Hollywood during her teenage days. He was her first boyfriend; she never even kissed a guy yet not held hands with anyone special. Valderrama respected that about her but the two still grew apart to some degree, which caused their split. He later spread a false rumor about her, which she denied. According to the singer, it’s not like him at all and she just wondered where all of the lies came from. Valderrama apologized and the rest became a laughing childhood memory. Moore later admitted that she loved him and that they are now friends.
36. Wilmer Valderrama and Lindsay Lohan
Another one of Wilmer Valderrama’s former lovers is none other than the 90’s to 2000’s teen queen herself: Lindsay Lohan. Valderrama and Lohan had chemistry and that we won’t deny, credits to their extreme good looks.
Valderrama was Lohan’s first high profile boyfriend. With the level of fame they both had, they decided to announce their relationship publicly after the actress turned 18. It was safer and less controversial that way as Valderrama was seven years older. Their relationship was described as not too deep but that didn’t stop Lohan from releasing her single Over after they broke up, which was about her heartbreak from Valderrama. Their relationship was over when Lohan had a series of unfortunate events in her life. She also admitted that she likes dating girls too. Valderrama, on the other hand, was labeled an official Hollywood playboy.
37. Jessica Biel and Chris Evans
Credits to Jessica Biel’s charm and superpowers, she won the heart or heartthrob Justin Timberlake, the man whom all the ladies during the 2000’s prayed so hard to marry one day. However, before their big happy ever after, Biel was involved romantically with Chris Evans.
It looks like the actress has a habit of dating extremely good-looking guys in Hollywood. This is a pair which most people forget. Some intentionally chose not to take a trip down memory lane since they are such huge JT fans, but Captain America and Biel were together for a long time too. They dated form 2001 to 2006 before Evans broke her heart. That didn’t stop Biel from acknowledging her former beau as a keeper. She said they discussed marriage when they were together, and he surprised her with the most romantic gesture she’s ever gotten: rose petals all over her bed on her birthday while she was still asleep.
38.Gwyneth Paltrow and Brad Pitt
Many may have forgotten already that once Gwyneth Paltrow and Brad Pitt were a couple. Paltrow and Pitt got together on the set of the film Se7en, where they portrayed a husband and wife. The two were smitten by each other and began their relation, which lasted until 1997. Paltrow and Pitt are among the most good-looking and talented actors during that time. In fact, them being together was considered the Brangelina of the 1990s. There was no denying that they are really in love with each other to the point that Pitt had asked Paltrow to marry him. Unfortunately, they did not end up tying the knot as the lovebirds split in 1997. According to Paltrow, it was her fault. She credits her young age and immaturity for their breakup. She even had it really hard that she could not eat because of it. The two moved on in a matter of time and found love with someone else. Pitt married Jennifer Anniston, while Paltrow dated Ben Affleck until 2000.
39.Ryan Reynolds and Alanis Morissette
For those who do not know, Ryan Reynolds and Alanis Morissette were once engaged to be married. As years went by and Reynolds got big, he is now known for his box-office hits and well associated with his marriage and family life with Blake Lively.
In 2002, Reynolds and Morissette started dating. They give credit Drew Barrymore for inviting them to her party that year which led to their relationship. Morissette was already a music personality since 1995 for her hit album Jagged Little Pill, while Reynolds had just gotten his big break when he landed the Van Wilder role in 2002. The couple was often part of Hollywood news scoop as they attended events together. At some point, they even got engaged in 2004. Sadly, they called it off and broke up after three years of being engaged and five years of dating. They chose not to divulge the reason for their separation in respect for each other, but the You Oughta Know singer hinted that their high profile is the cause. Reynolds later met Lively on the set of Green Lantern in 2011 and married her in 2014. Morissette found the kind of love she wanted with the rapper Souleye, with whom she shares three children.
40.George Clooney and Lucy Liu
Everyone once thought that George Clooney was the kind of man who would never settle, until = Amal Alamuddin entered his life with her sophistication and brains. While everyone was happy about their union, some viewed Mr. Clooney is their one who got away.
Ever since the actor started his career, his dating life was always a hot topic. Prior to meeting his lawyer wife, he was notoriously known for his bachelor lifestyle and his fear of commitments. Clooney was not afraid to admit his involvement with women, but his rendezvous with Lucy Liu was an exemption. He and Liu were rumored to date in 2000 since they were often spotted together, yet they never admitted to having a relationship despite being captured locking lips on New Year’s Eve 2006. Apparently, things were a bit off for both of them as Clooney started dating Lisa Snowdon. As years went by, both of them walked down different paths. Liu has never married but has a son via gestational surrogacy, while Clooney ended up getting married at becomes a father at the age of 56.
41.Reese Witherspoon and Jake Gyllenhaal
Though the world is busy with the boom of technology, everyone was shocked when Reese Witherspoon and Ryan Phillippe announced their separation in 2007. While most Ryan-Reese fans can’t get over their split, it was a surprise to everyone when Jake Gyllenhaal became her new beau.
The actors met while filming Rendition in 2007. Though the two knew each other through Phillippe since Gyllenhaal was his gym pal, Witherspoon started seeing him in a new light. Admittedly, she developed a little crush on him as they get to know each other, and the two soon became a couple. Apparently, their relationship was put on hold as she was still dealing with her lawyers regarding her separation. In 2008, Gyllenhaal and Witherspoon got back together and made their relationship known to the public. They broke up in 2009 as the actress was not ready to remarry. Despite everything, Gyllenhaal holds no grudge against her and still praises her whenever there is an opportunity.
42.Tom Cruise and Cher
Tom Cruise and Cher happened. Though it was not a secret, Cher further revealed intimate details about their romance that started with a simple hi. Before Cruise got big in the industry, he once had a lot of adventure as a young man. As such, it includes his relationship with Cher, who is 16 years his senior. When they met in 1985, the actor was just 23 while Cher was already 38. Many thought it was just a fling, but Cher said in an interview that it was more than just a fling. Cher admitted that she had moved into his apartment and was crazy about him. Cher added that she adored the shy boy that Cruise was once. After all, this was when he has not yet gained much credit score. Knowing Cher, she was not shy about sharing the intimate details of her life. As such, she also ranked the actor as one of her best lovers. Cher also revealed that they first met during Madonna and Sean Penn’s wedding, but it was their meeting at the White House where they got the chance to spark a connection over their dyslexia.
43.Emma Stone and Kieran Culkin
Remember when Emma Stone and Kieran Culkin were an item? Well, most might say no, but to tell honestly, Kieran was the first of her few relationships before meeting husband Dave McCary.
Stone and Culkin met in 2009 while filming Paper Man. The film did not go well in the box office despite its stellar casting, including Ryan Reynolds and Lisa Kudrow. The two dated for almost two years until they bid farewell in 2011. Subsequently, Stone started to gain attention and make a name for herself when she starred in Zombieland in 2009, followed by acting credits in Easy A and The Help, which both came out in 2011. No one knows the reason for their split as they have been very private about their relationship, and no one bothered to ask. There are many factors to consider why their relationship did not gain attention from the media, but they are now happily married to other people, so we are sure there is no bad blood between them.
44.Mark Ronson and Rashida Jones
Among the relationships who got lost in time are Mark Ronson and Rashida Jones. Some may not know that the two dated, so here are the things we unearthed about their time together.
Ronson is a famous music producer who has produced many hit tracks, such as Uptown Funk, sang by Bruno Mars, and Shallow by Lady Gaga and Bradley Cooper. Meanwhile, Jones is the daughter of the musician Quincy Jones and actress Peggy Lipton. She gained popularity as an actress and filmmaker. As such, she received praises and credits for her documentary about her father in the 2018 film Quincy. Jones has dated several high-caliber actors and personalities in the past, including John Krasinski, Colin Jost, Seth Meyer, and Charlie Hunnam. Before all those happened, she was once in a relationship with Mark Ronson for two years. They must have met through their involvement in music, given that her father is a famed music producer, and so is Ronson. In 2003, he proposed to Jones using a custom-made puzzle, but the two parted ways in 2004 for unknown reasons.
45.Mila Kunis and Macaulay Culkin
Mila Kunis and Macaulay Culkin are both child actors who entered the industry at a young age. They started dating in 2002, when Kunis was 18 and Culkin was 21. She was just starting her career, having just concluded her stint from That ‘70s Show, while he was a successful child star who tried to have a life outside of the limelight. According to Kunis, she and Culkin grew up together and became each other’s solace. Unfortunately, their relationship ended in 2011. The actress recently admitted that it was a horrible breakup and she was the one at fault. She credits her immaturity and her lack of self-control for their nasty split while dismissing the cheating rumors. The two have sinced moved on and are now on good terms. Kunis is now married to Ashton Kutcher, with whom she has two kids, while Culkin recently welcomed his first child with actress Brenda Song.
46.Ben Affleck and Gwyneth Paltrow
In 1997, just after Gwyneth Paltrow and Brad Pitt split, she started a romance with Ben Affleck. Though their relationship lasted for three years, with the actress admitting that she did not see herself marrying him.
Paltrow and Affleck first met during a dinner. They starred in the films Shakespeare In Love and Bounce. Their relationship was well-received by the media as they were both at the peak of their careers at the time. In 2000, the two split and did not say a word about it until in recent years when Paltrow spoke about her past relationships during an interview. She mentioned how she knew that she and Affleck were not going to end up together as she was still in the healing process from her previous relationship to some degree. She added that he was kind of complicated in terms of handling relationships. Additionally, she mentioned that their differences, especially in terms of values, made them incompatible in the long run.
47.Nick Jonas and Selena Gomez
Back in 2008, Nick Jonas and Selena Gomez were once a couple. Their budding relationship quickly ended as the pair was at the peak of their career: was with his famous boyband, Jonas Brothers, while Gomez was making the airwaves love her songs. In 2018, the Love You Like a Love Song singer reminded her former beau about how bad their day at Central Park went. Jonas explained that he decided to stand 25 feet away from her as they were being followed by the media. Additionally, the actress was with her famous friend, Taylor Swift. While their relationship did not push through, it seems the two do not have bad blood between them whatsoever. Now, Jonas is married to Priyanka Chopra, while Gomez is happily single. In addition, she just launched her newest investment, the makeup line Rare Beauty.
48.Leonardo DiCaprio and Gisele Bundchen
Leonardo DiCaprio has dated several models in the past years. Most did not last long, with the exception of his relationship with Gisele Bundchen. In 2000, the two were spotted hanging out together. Bundchen was a rising supermodel at that time, while DiCaprio already had several acting credits. As the actor’s love life was always a spectacular media event, the model immediately rose to the spotlight. At first, they kept tight-lipped about their connection, only confirming their relationship in 2003. Two years later, the couple called it quits. DiCaprio went on to date another gorgeous woman while Bundchen met Tom Brady in 2006. In her memoir, she briefly wrote about her relationship with her former beau. At a certain point, Bundchen wrote that she was in a bad state and needed a shift in life, but he was not on board and wanted things to remain the same.
49.Alyssa Milano and Justin Timberlake
The singer Justin Timberlake’s dating life was a media favorite before he met his wife. He has dated several high-profile personalities such as Cameron Diaz, Fergie, and Britney Spears. Alyssa Milano came forward and talked about their short time together in 2002. The actress is known for her acting credits as Phoebe Halliwell in Charmed and as Jennifer Mancini in Melrose Place.
According to her, she and Timberlake dated for a few months. Their relationship was so short-lived that it did not even reach the media’s attention. She later admitted that after Timberlake’s romance with Spears, she hooked up with him in 2002. Aware that the Cry Me a River singer was not over his ex, she decided to call it quits. Now, Timberlake has been married to Jessica Biel since 2012, while Milano has been with her husband David Bugliari since 2009.
50.Blake Lively and Penn Badgley
Gossip Girl fans can attest how Blake Lively and Penn Badgley looked good together. Their on-screen chemistry as Serena van der Woodsen and Dan Humphrey was like Romeo and Juliet in a different setting. As good as it gets, the on-screen chemistry became a reality when they were captured locking lips during a vacation. Admittedly, the actors initially tried to deny the rumors of their coupling as they fear it will not please their bosses and might wreck their young careers. On the flip side, the management was pleased about their romance as they thought it could do good for the show. Their relationship came to an end in 2010 after three years of dating. The two split amicably and did not let anyone know about it. As such, they were given high credits for their professionalism as their breakup did not affect their chemistry on set.
51.Blake Lively and Leonardo DiCaprio
In 2011, Blake Lively and Leonardo DiCaprio were a couple but dated for just five months before going their separate ways. Before their pictures were out on tabloids, the actor had just ended his relationship with Bar Rafaeli. Meanwhile, Lively’s romance with Penn Badgely ended in 2010. Unlike their previous relationships, the actors were not timid about public displays of affection.
According to reports, they first met during auditions for The Great Gatsby. Lively allegedly auditioned for the role of Daisy and was thought to have snagged it as she was spotted having dinner with DiCaprio. Carey Mulligan wound up getting the part, which sparked dating rumors. Months after, they made their relationship public. They were seen doing a lot of fun activities together, including biking in the busy streets of New York. While their moments seem so endearing, they did not last long. It did not take long as well before a new guy came into the picture. Lively got together with Ryan Reynolds just months after the breakup. Now, she is happily married to Reynolds and is busy helping their kids with their online classes.
52.Nicolas Cage & Lisa Marie Presley
Nicolas Cage once said that he did not consider his relationship with Lisa Marie Presley a real marriage as it did not last long. Looking back at their tumultuous relationship dating back to 2000, the two had an on-and-off relationship that lasted for years. Eventually, Cage and Presley got married in 2002 at a lavish wedding in Hawaii. However, their marriage was short-lived and the Ghost Rider actor called his lawyers to have their marriage annulled after just four months. As said earlier, they did not have a smooth-sailing relationship. They often fight about petty things, with Presley saying they were like kids in a sandbox. Although they adore each other, it seems their personalities did not match, for that they decided to end their relationship before they tore each other apart. They have since moved on to other people. Cage recently got married to Riko Shibata, while Presley was married to Michael Lockwood from 2006 to 2016.
53. Brooke Shields & Andre Agassi
The actress Brooke Shields married tennis player Andre Agassi in 1997. The two had been in a relationship for four years by the time they got married. Sadly, the two parted ways after two years of marriage. In an interview on The Today Show, Agassi talked about their relationship, stating that he wasn’t in a place where he could be married to anyone. He added that he didn’t understand himself at the time, which led to the downfall of their relationship.
In her memoir, Shields talked about how Agassi was the first man who had ever swept her away. She added that their relationship was “so necessary.” She also recalled an agonizing conversation she had with Agassi during their own legal separation proceedings and encouraged other spouses to be aware and vigilant of the complexities when ending a marriage. Whether it’s lawyers or the division of assets, separating from a spouse can be painful. Despite how things ended for them, there is no bad blood between them.
54. Halle Berry & David Justice
Halle Berry’s first ever marriage was to David Justice, a baseball player who once signed with the New York Yankees and was a three-time MLB All-Star. They got married in 1993, but their marriage was a tumultuous one and unfortunately did not last. They separated in 1997. Berry was also granted a temporary restraining order following their legal separation. The ex-Atlanta Braves player defended himself from allegations by saying that as a baseball player back in those days, he did not have a team to help him deal with the press, while Berry had managers, lawyers, and publicists working for her.
Though there relationship had a bitter end, the former lovers have since moved on with their lives. Justice has been married to Rebecca Villalobos since 2001, while Berry is currently in a blissful relationship with the musician Van Hunt.
55. Richard Gere & Cindy Crawford
People couldn’t stop talking about Cindy Crawford and Richard Gere back in the day as they were deemed as one of Hollywood’s most iconic couples. They were both in the peak of their careers when they got together. Looking back on her first marriage, Crawford thinks she and Gere should have built a solid foundation of friendship before they got together. She said that it would have helped their relationship immensely as they both evolved as individuals. Their 17-year age difference also provided a degree of difficulty.
The couple had a lot on their shoulders due to the attention they received from the media. Everyone against them, which only made matters worse for the two. Eventually, their relationship fizzled out. In 1995, Gere and Crawford made publicly announced that they were separating after being married for only four years. Their iconic relationship now remains only in our memory.
56. Chad Michael Murray & Sophia Bush
Chad Michael Murray and Sophia Bush started dating the same year One Tree Hill was released. They were married two years later after getting engaged while on vacation in Australia. They tied the knot at Hotel Casa Del Mar in Santa Monica, California in the following year. Murray and Bush became one of young Hollywood’s hottest couples.
After five months of marriage, their relationship suddenly crumbled and the actress filed for annulment with the help of her lawyer. After their split, the couple is currently not on good terms. However, they put their differences aside and continued to work together until One Tree Hill aired its final season in 2012. Bush discussed their short-lived marriage on Watch What Happens: Live, stating that they were both young and foolish at the time. She also dated another One Tree Hill co-star, James Lafferty, from 2008 to 2009.
57. Drew Barrymore & Tom Green
This may come as a surprise to some, but Drew Barrymore was once married to Tom Green. After the Golden Globe-winning actor signed on to produce and star in the 2000s film Charlie’s Angels, she crossed paths with the comedian, who she wanted to feature in the movie. He was eventually cast as The Chad. “She and the studio were trying to get me in that movie for a while,” Green said on The Alan Cox Show in 2018. “I actually passed on it initially.” After agreeing to be in the movie, the two began dating. The couple got engaged and tied the knot in July 2001. They separated in December of that year.
Although Barrymore and Green’s marriage was one of Hollywood’s most compelling celebrity marriages, the Charlie’s Angels star believes she and her former husband were “idiots” for tying the knot when they did it. She explains that they were young, and she did not know how to handle things in her personal life. After not talking for 15 years, Barrymore and Green reunited in an episode of The Drew Barrymore Show. To their credit, they appeared to be on good terms with each other.
58. Eva Longoria & Tyler Christopher
Tyler Christopher and Eva Longoria’s romance and marriage transpired to an extreme degree of privacy that they were long separated by the time their fellow celebrities and their viewing audience fully understood and realized the true extent of their relationship.
Christopher said they were in an on and off again relationship. The couple eloped in Las Vegas, after a few consecutive “on” months. The ceremony was held on January 20, 2002, and witnessed by Freddie Prinze, Jr. and Sarah Michelle Gellar. Longoria later declared that marriage was harder than they thought. They found it difficult to adjust to the other’s lifestyle. “We both have our habits that we won’t give up,” Longoria revealed in an interview one year after tying the knot. In September 2008, the Desperate Housewives actress finally broke her self-imposed silence and offered a few candid remarks about her ex and their brief marriage.
59. Zooey Deschanel & Ben Gibbard
Zooey Deschanel and Ben Gibbard’s relationship has long been buried in our collective memories. Let this remind you that there was once a time that they were a thing. In 2008, they began dating and got engaged that same year after nearly a year together. In 2009, they got married, and two years after, they legally separated with the help of their lawyers. The records of their split were made public when their separation was finalized in 2012. The former couple cited irreconcilable differences.
Since their separation, they have both since remarried and moved on with their lives. Gibbard, who is the frontman for the band Death Cab for Cutie, released an album called Kintsugi in 2015. Fans speculated that the album contained songs about the New Girl actress, which he confirmed, though he refused to name which songs were about her.
60. Carmen Electra & Dennis Rodman
Carmen Electra first became involved with Dennis Rodman, the Chicago Bulls’ key defensive player and eccentric free spirit, in 1998. Their wild and bad romance, fueled by outrageous behavior and marathon parties on hotels and roofing in Las Vegas, was a headline-grabbing sideshow during the Bulls’ quest to win their sixth championship.
Their intense love affair ended in separation, with both parties filing for annulment nine days after they got married in Las Vegas. They reconciled for four months before ending things for good. In an interview with ET Online, Electra says Rodman, who was the bad boy of the NBA, was addicted to her when they first met and constantly called her until she picked up. She added that their relationship had a lot of highs and lows, but that she ultimately wishes the best for him. Nowadays, the former lovebirds rarely speak but still share the same agent.
61. Angelina Jolie & Billy Bob Thornton
Angelina Jolie and Billy Bob Thornton met, exchanged a few looks here and there, and started a relationship while filming the 1999 film Pushing Tin, where they played a husband and wife. Their instant connection continued to spark like electricity, with the two eloping in Las Vegas the following year.
Their relationship was full of wackiness and chaos. They swapped underwear, got matching name tattoos, and were not shy about public displays of affection. After just two years of tying the knot, Jolie and Thornton separated in August 2002. It was also the same year the Maleficent star adopted her first child, Maddox. The actress says they just grew apart and became different people. She became more politically active, while he was focused on his music career. Despite going their separate ways, both Jolie and Thornton still held each other in high regard and are friends to this day.
62.Kaley Cuoco and Ryan Sweeting
The Big Bang Theory star Kaley Cuoco dated professional tennis player Ryan Sweeting for three months before marrying him in December 2013. The pair announced their separation in September 2015, with a representative for Cuoco saying they had “mutually agreed to end their union.” It was also the actress who filed for separation, citing irreconcilable differences.
Sweeting already made his degree in the tennis scene and won his only ATP World Tour singles title under his belt before starting dating Cuoco. Thanks to an ironclad pre-nuptial agreement, the actress will keep her Big Bang Theory fortune. Sweeting received just $165,000 from the marriage. Cuoco also paid $195,000 for his two personal trainers in exchange for their Tarzana home and a Santa Barbara beach house. Sweeting would still be entitled to retain whatever money or “gift cards” he earned after their brief union.
63.Katy Perry and Russell Brand
In their respective careers, Katy Perry and Russell Brand both earned degrees of success. The singer rose to fame in the music industry for her singles I Kissed a Girl and Firework, while Brand established himself as a stand-up comedian. After several flirtatious encounters during the 2009 VMA rehearsals, the two started dating and fell in love almost instantly.
Brand went from being Perry’s first husband to ex-husband in a matter of months. He called it quits on the relationship. In fact, it only took one text message to tell the Roar singer that he was divorcing her after fourteen months of marriage. According to reports, they were drifting apart just before the breakup and didn’t even spend Christmas together. It was unexpected; the couple who were so confident of each other called it quits. The comedian claims that his former wife’s popularity and demanding work schedule pushed him away.
64.Wiz Khalifa and Amber Rose
From July 2013 to September 2014, the model Amber Rose and rapper Wiz Khalifa were married. Sadly, after a year of marriage, they publicly revealed that Rose had applied for legal separation and sought sole custody of their then-1-year-old son, Sebastian. According to TMZ, the explanation for the breakup was rumors of infidelity, but Rose denied the accusations. In the filing with her lawyer, she cited “irreconcilable gaps.”
Regardless of how things ended between them, Rose has declared that Khalifa is the only man she has ever loved, even calling him the “love of my life”. Despite this, they both know that they don’t work well together as a couple and that they are better off as friends. They have also worked out a co-parenting setup that works for them. Rose has since welcomed another child, Slash, with her current partner Alexander Edwards.
65.Carey Mulligan and Marcus Mumford
Carey Mulligan and Marcus Mumford have a love story to remember. The two met as childhood pen pals and later reconnected as adults, falling in love with each other. Since marrying in 2012, the English actress and Mumford & Sons frontman have built a life together in the English countryside, where they now live with their two daughters. The couple wouldn’t have to think about any mortgages in their countryside home. After all, they have a combined net worth of $26 million.
In April 2012, more than 100 of the pair’s closest friends and family members, including Jake Gyllenhaal, Sienna Miller, and Colin Firth, gathered in a quaint barn in Somerset, England, to see the couple exchange vows. The romantic ceremony was officiated by Marcus’s father, John Mumford, a vicar. The bride wore a backless ivory gown designed by Prada, who also designed her first Oscars look.
66.Seal and Tyra Banks
Tyra Banks is a television host, model, businesswoman, producer, actress, and journalist who is best known for her work on America’s Next Top Model. She and fellow model Heidi Klum have a lot more in common than just modeling. Aside from walking the Victoria’s Secret Fashion Show together and posing together in numerous advertisements, they also share an ex: the singer Seal. Klum was married to Seal for over a decade, while Banks dated him for a few years.
Seal and Banks dated briefly in 1996 after she caught the singer’s eye. They somehow managed to keep their relationship private despite being influential figures in their fields. They only attended the Essence Awards as a couple once. The relationship only lasted a few months, ending in October 1996. After their split, Banks has had television appearances as well as several lifestyle investments.
67. Neil Patrick Harris and Christine Taylor
Neil Patrick Harris is openly credited as an actor, singer, comedian, writer, producer, and television host. He rose to fame after starring in the TV show Doogie Howser, M.D. He then appeared in various films like Starship Troopers and Gone Girl. At one point, Harris, who is openly gay, dated the actress Christine Taylor. They were in a relationship from 1997 to 1998. During an interview with Howard Stern, he opened up about his relationship with her.
He said that the romance made him realize his sexuality. He added that she was “an absolute catch”, but there were no sparks of electricity for him. Harris continues to speak highly of Taylor and thanks her for everything she’s ever done for him. In 2000, she married the comedian Ben Stiller. Harris, on the other hand, came out in 2006, several years after his relationship with her, and is happily married to David Burtka.
68. Matthew Perry and Julia Roberts
Did you know that Matthew Perry and Julia Roberts went on a couple of dates back in the 1990s? Yup, these two had a thing before after they worked together in an episode of Friends. Julie played the credit role of Chandler’s love interest, Susie Moss, at the time. It looked like she really did catch the actor’s interest since their fictional romance turned into something real.
Their love, however, was only brief. They only dated for a year, with Roberts being Perry’s first-ever public relationship. Though it was only a short-lived love affair, fans would never forget these two made their feelings from reel to real. A fan page even shared a series of their snaps when they were young. In the photos, the couple was walking the streets of Los Angeles. It seemed like they snuck out to meet as Roberts was barefoot in the photo, while Perry was wearing socks.
69. Ryan Reynolds and Kristen Johnston
When Ryan Reynolds was only starting in the business, he began to have a relationship with Kristen Johnston. It was only a short one, however, that only lasted for a few months between 1999 and 2000. They were also photographed attending the premiere of The Green Mile.
Their relationship happened so long ago that Johnston herself couldn’t remember what it was like to date the Hollywood heartthrob, but she still gave the actor credit for being a nice, lovely person and a “great guy.” Those were the only words she could say about their romance, and she chose not to divulge further information about their brief affair. The actress is currently single. The only known relationship she has had since then was with David Newsom. Reynolds, on the other hand, is now married to Blake Lively and has three lovely children: Inez, James, and Betty.
70. Uma Thurman and Gary Oldman
Uma Thurman’s famously known husband is Ethan Hawke, though the two have been separated since 2005. It looks like not everybody knows she was once married to a great actor himself, Gary Oldman. The two tied the knot in 1990 and ended things after just two years, thanks to their lawyers.
If you envy her romance with the actor, think again—she called it a “mistake.” Thurman revealed they met when she was only 18 years old, while Oldman was already 30, making him 12 years her senior. The actress described their romance as a “crazy love affair” that needed to end. The Harry Potter star was her first love, and she had no prior experience. Thurman couldn’t deny, though, that Oldman is “truly” an excellent star. Well, the 63-year-old filmmaker wouldn’t be called one of the greatest actors of his generation for nothing.
71. Lance Bass and Danielle Fishel
Danielle Fishel is an actress who is currently happily married to producer Jensen Karp. She rose to fame during her teenage years back in the ‘90s for her role in the sitcom Boy Meets World. If you were a big fan of hers back in the day, you probably remember that she had a relationship with NSYNC member Lance Bass. Their relationship was the talk of the town, especially amongst the teens. They even went to prom together.
Nowadays, Bass is a proud member of the LGBTQ+ community. He announced that he was gay back in 2006. Before that announcement, he was a member of the heartthrob boy band NSYNC along with the likes of Justin Timberlake. This is one of the reasons why his relationship with Fishel was held to such a famous degree by his adolescent fans. Those who followed their relationships back in the day would be pleased to know that the two of them stayed good friends even after their break up.
72. Chris O’Donnell and Reese Witherspoon
Reese Witherspoon’s breakout performance was in the movie Cruel Intentions in 1999. She would then solidify her claim to fame with the movie Legally Blonde. The film’s commercial success and acclaim would also lead to a sequel and further open the gates of opportunity to the actress. In 2005, she would do her award-winning performance in the movie Walk the Line, portraying June Carter Cash. For this, an Academy Award was given to her credit.
Long before all these though, Witherspoon began her acting career during her teenage years. Her screen debut was in the film The Man in the Moon in 1991. Back in those days, she was rumored to be in a relationship with Chris O’Donnell, who was also on the rise to fame. He was known for his performance in Scent of a Woman and for portraying Dick Grayson in Batman Forever and Batman & Robin movies.
73. Ellen DeGeneres and Anne Heche
Anne Heche was a soap opera star back in the late ‘80s. To her credit, she has an Emmy Award and two Soap Opera Digest Awards for her performances in the show Another World. She then made a breakthrough to the mainstream in a string of commercially successful movies which include I Know What You Did Last Summer, Donnie Brasco, Return to Paradise, Six Days, Seven Nights, and Volcano. Back in those days, she was also known for her relationship with comedian Ellen Degeneres. Their relationship spanned for over three years from 1997 to 2000.
Degeneres is best known for her talk show, The Ellen Degeneres Show. Over the years, the talk show has earned the comedian countless accolades. She has interviewed countless of A-Listers such as Brad Pitt and Chris Evans, as well as distinguished public figures such as former President Barack Obama.
74. Matt Damon and Minnie Driver
Matt Damon is one of Hollywood’s most talented actors. He is known for portraying a wide variety of characters. If you’re a fan of the action genre, then you must love him in action thrillers, such as the Bourne franchise, Ocean’s 11, The Departed, and Saving Private Ryan. Or if drama is more to your liking, then Invictus, Interstellar, Contagion, and The Martian. His breakthrough performance, though, was in 1997 in the movie Good Will Hunting. The film was written by Damon and his long-time close friend Ben Affleck. To their credit, the movie received much acclaim from critics and viewers and several accolades from prestigious awards shows. Aside from the awards that Damon got out of this iconic film was his relationship with co-star Minnie Driver. Their on-screen chemistry transcended the silver screen and they dated for over seven months after filming the movie.
75. Notorious B.I.G. and Faith Evans
Christopher Wallace was professionally known as The Notorious BIG. He grew in New York City and lived a colorful adolescent life. He then left school by the age of 17 and started his journey as a rapper. He was famous for his friendship and partnership with fellow rap star Sean Combs or Diddy. In 1993, they started the record label Bad Boy Records. The Notorious B.I.G. is also famous for his collaborations with the likes of Busta Rhymes, Mary J Blige, and LL Cool J. In 1994, he released his debut album and, to his credit, it was the beginning of his rise to becoming one of the most distinguished rappers of his generation.
During those years, the rapper was famously married to fellow musician Faith Evans. They were married in 1994 up to his untimely death in 1997. The distinguished rapper, during that time, was oftentimes painted in a bad way due to rumors of infidelity. Later on, Evans would go on to say that their marriage was highly sensationalized by the entertainment media.
76. Joaquin Phoenix and Liv Tyler
Liv Tyler is the famous daughter of rockstar Steven Tyler. Though she did not follow her father’s footsteps in the music industry, she did make a name for herself in Hollywood. She was once married to Royston Langdon, but you probably remember her relationship with distinguished actor Joaquin Phoenix. Tyler is famous worldwide for her role in the Lord of the Rings franchise and movies such as Armageddon, Reign Over Me, and Inventing the Abbotts, where she co-starred with Phoenix. They kept their relationship a secret for a time and even kept it hidden from their coworkers. In an interview the actress did with The Morning Call, she confessed to falling in love with him the moment she met him. Their relationship lasted for three years until they decided to mutually part ways. They even have the fortunate insurance of being good friends even after their break up.
77. Luke Wilson and Drew Barrymore
Drew Barrymore has lived her life in the limelight. She gained her celebrity status at a young age after starring in Steven Spielberg’s iconic ET: the Extra-Terrestrial. Barrymore is also widely recognized for her comedy films, particularly a string of movies she did with Adam Sandler. These include The Wedding Singer, Blender, and 50 First Dates, the first of which received such a degree of commercial success that it opened several other opportunities for the young actress.
In 1998, just after filming The Wedding Singer, Barrymore starred in the rom-com film, Home Fries. This is where she co-starred alongside her former boyfriend Luke Wilson. The director of the film, Dean Parisot, hit the jackpot with this duo for their apparent chemistry. He even went out to say that he saw the couple falling even deeper in love as they look into each other’s eyes during filming some of the scenes of the movie. Wilson and Barrymore were in a relationship for two years.
78. Ted Danson and Whoopi Goldberg
Ted Danson and Whoopi Goldberg starred in the romantic comedy flick Made in America. The film was a commercial success, but it also sparked electricity between the two lead stars. It seemed like that Danson and Goldberg’s onscreen chemistry was more than just an act and seeped out to their personal lives for the actor to take a chance with her. And took a chance he did, though it also resulted in controversy. Their love stint lasted for only one year before they eventually parted ways in 1993.
Nowadays, Danson is one of TV’s well-decorated actors. He has won several accolades, such as two Emmy Awards and three Golden Globe Awards. His most distinguished character would be in the series Curb Your Enthusiasm. On the other hand, Goldberg is also known for her TV success as a co-host on The View.
79. David Arquette and Alyssa Milano
Nowadays, the younger generation probably knows of Alyssa Milano for her noble political activism. For those of us who grew up in the 1990s though, we fell in love with her in the series Charmed. At that time, she was already an established television actress. Milano had starred in the sitcom Who’s the Boss. The show is recognized to be one of the most popular sitcoms during the 1980s and also won several accolades such as a Golden Globe and an Emmy Award to its credit.
In 2013, Milano did an interview where she revealed one of her long-kept secrets. She confirmed that at the tail end of Who’s the Boss, she was in a relationship with David Arquette. During that time, the actor was starting his film career, starring in movies such as Buffy the Vampire Slayer, At Home with the Webbers, and Airheads.
80. Edward Norton and Drew Barrymore
As we now know, Drew Barrymore had a romantic relationship with her co-star, Luke Wilson back in 1998. It may come as a surprise to you but this was not the first time that the young actress fell in love with her co-star. In 1996, she had a relationship with her Everyone Says I Love You co-star Edward Norton. Although their relationship would be better categorized as a fling, for it lasted less than a year, surely, they must have the insurance of sharing some of the best times of their lives.
After their fling in 1996, Norton would go on his prolific rise to Hollywood esteem. He is known for his great artistic talent as an actor in movies such as American History X and Fight Club. In the 2000s, he also furthered his Hollywood career by producing or directing films such as Down in the Valley, Keeping the Faith, and Down in the Valley.
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