It is challenging for celebrity couples to hide their relationships because there are paparazzi everywhere. Besides that, it has become much more difficult in recent times due to smartphones and people on social media. However, back in the day, it was much easier for many couples to keep their relationships on the down low. Here are the top fifty celebrity couples that dated back then, and you might have forgotten about them because their relationship was low-key. Let this list serve as a reminder of their dating attempts and their progress since then. Keep reading to learn more about them.
Matthew McConaughey And Sandra Bullock
Matthew McConaughey and Sandra Bullock began dating in 1996 after they met on A Time to Kill. The best part is that they stayed under the radar, as they did not make their relationship too public. We still don’t know why they ended up breaking up, but there could have been a timing issue, according to sources. That is because both the stars have been incredibly ambitious, which is why they found it difficult to make time for their relationship. We don’t know for sure, but these are the reasons that they might have broken up. Of course, it has been a long time since then, and both have dated other people.
Nicole Kidman And Lenny Kravitz
After her divorce from Tom Cruise, Nicole Kidman started a secret relationship with Lenny Kravitz. They were also engaged for a while in 2003, but she wasn’t ready to get married, so the pair did not end up marrying. However, you will find that they are still on good terms, as she has also worked with his daughter. Kidman and Zoe, Kravitz’s daughter, starred together in the Big Little Lies series. So, there is no bad blood between the two, and they had a significant impact on one another when they were dating. The connection was short-lived but strong enough for them to be on good terms.
Jake Gyllenhaal And Reese Witherspoon
Jake Gyllenhaal and Reese Witherspoon met when they were filming Rendition. After that, they began dating for two years, between 2007 and 2009. The relationship ended well, as both of them decided it was time to part ways on good terms. There is speculation that the couple parted ways because Witherspoon was reluctant to remarry after her past experiences. Even though she was committed to family, she still had no idea how she felt about getting married at the time. There were rumors that one of them cheated, but sources told Us Magazine that this was not the case at all.
Alanis Morissette And Ryan Reynolds
Before Ryan Reynolds found the love of his life, he was dating Alanis Morissette. The couple dated for a year and got engaged for three years before they decided to part ways. They are still good friends and have a lot of respect for one another. It is great to see when Hollywood couples end on good terms and respect each other even after breaking up. Now, Reynolds is married to Blake Lively, and they have beautiful children together. They are also one of the top power couples in Hollywood and all over social media, as they are incredibly open about their marriage.
Macaulay Culkin And Mila Kunis
Macaulay and Mila started dating in 2002 when they were young, as he was 21 at the time and Mila was 18. They began dating long-distance as Macaulay was in New York City and Mila was in Los Angeles. Both of them dated one another for eight years before they split. She is now happily married to Ashton Kutcher, as they met when they were shooting on the set of That 70s Show. Not many people know about their relationship because they kept it low-key. However, their breakup was horrible, and Kunis will always regret the way that they broke up with him.
Penn Badgley And Blake Lively
The stars were not only hot and heavy on screen as they also dated for three years, between 2007 and 2010. Penn had an interview with Elle Magazine after their breakup, and he described their relationship as a learning experience. Lively met Ryan Reynolds the same year that she and Penn split. Of course, Blake and Reynolds are happily married, and they are expecting their fourth child together. We are incredibly happy that Blake Lively found her happily ever after, and the couple is one of the most beloved in Hollywood. Penn has been married to Domino Kirke for the past five years now.
Gisele Bundchen And Leonardo DiCaprio
Leonardo and Gisele began dating when they were both young, as he was twenty-five and she was twenty at the time. Their relationship lasted for five years, and they were seen together at the Oscars in 2005. The couple ended their relationship amicably, and they are still good friends. Bundchen still respects Leonardo DiCaprio as a human and an actor. Of course, Leonardo has had a colorful history of dating young women, and he has been notoriously famous for it. His list of women that he dates keep increasing with each passing year and Bundchen is rumored to be dating Joaquim Valente.
Renee Zellweger And Bradley Cooper
Bradley Cooper and Renee Zellweger dated for two years before they decided to split. The couple did not publicly acknowledge their relationship the entire time they were together. Because of this, they also did not give a statement about their breakup. However, there are many sources that tell us that the couple split because of the career ambitions of Bradley Cooper. They did have a sweet moment back in 2020 during an Oscar ceremony. Cooper went on to be married to Jennifer Esposito for a year, and he had a partnership with Irina Shayk between 2015 and 2019, as they share a daughter.
Jonny Lee Miller And Angelina Jolie
Angelina Jolie and Jonny Lee Miller were married once, and it has been over two decades since their divorce took place. However, their relationship is proof that exes can still be on good terms and friends. That is because the pair was spotted enjoying a meal a year ago, and they looked amicable and happy. Their marriage lasted for three years, and since then, Jolie was also married to Brad Pitt for five years before they called it quit in 2019. She has not married anyone since then, and she continues to be one of the top movie stars.
Samantha Ronson And Lindsay Lohan
We bet you didn’t expect to see Lindsay Lohan and Samantha Ronson on our list, but they dated for a year. Their relationship was short-lived, but it was also very dramatic and intense while it lasted. They were platonic friends for many years before they began dating in 2008. As they began dating, you would see Lohan and Ronson everywhere together. They also went on double dates with their moms and showed up at parties. Unfortunately, they split after a year of dating because they figured out that they were toxic toward each other, and so their story ended.
Courteney Cox And Michael Keaton
Michael Keaton and Courtney Cox were together for six years before she went on to become one of the most popular actresses of all time. They split up in July 1995, but their relationship was serious. The couple met when Courteney told a mutual friend that she really liked Keaton in Clean and Sober. The first date that the couple had was at her house because they did not want the media to know about their relationship. Later on, Cox got married to David Arquette, but they got divorced. However, they have one beautiful daughter together, Coco Riley Arquette.
Nick Cannon And Kim Kardashian
Kim Kardashian and Nick Cannon were dating five years before Kim began dating Kanye. Nick and Kim began dating in 2006 and decided to part ways a year later. According to Nick, Kim was the one to dump him, and she left him with a broken heart when this happened. After that, Kim also dated Ray J, and her sex tape with him was the one that made her incredibly famous. Since then, Kim has been married to Kanye West, but the couple has called it quits now. Her dating life has always been tumultuous, and that adds to her fame.
Robert Downey Jr. And Sarah Jessica Parker
Many people wanted Sarah Jessica Parker and Robert to work out, but unfortunately, not all fairy tales have a happily ever after. Their relationship lasted for eight years, and they decided to part ways in 1991. During that time, Robert was struggling with addiction, and it was not easy for the couple to go through this. Their relationship was a fairy tale, and they also wanted to get married and have children. However, not everything works out the way you want it to. Parker and Robert split, and she went on to get married to Matthew Broderick to get her happily ever after.
Zac Efron And Michelle Rodriguez
Michelle Rodriguez and Zac Efron had a short fling that lasted for the duration of summer in 2014. During this time, the couple was spotted getting cozy in Spain. After the summer ended, it was said that the couple had split, and they were not seen each other since then. They only dated for two months, and they had incredible chemistry while they were together. Of course, that is not the only thing that can bind a couple together for a long time. So, both of them decided it was best to go their separate ways after the summer.
Gwyneth Paltrow And Ben Affleck
Ben Affleck and Gwyneth Paltrow dated between 1997 and 2000. They met while they were on the set of Shakespeare in Love, and they instantly hit it off. Their relationship was not too stable, and even during this time, they were dating on and off. Paltrow is also incredibly happy that Affleck has finally found his happily ever after with Jennifer Lopez. We are happy for both the stars because they went on to have successful relationships with other people. She is now married to Brad Falchuk, and they have been happily together since 2018.
Kate Bosworth And Orlando Bloom
Orlando Bloom and Kate Bosworth dated for two years before they decided it was time to part ways in 2005. According to the actress, they are still good friends, and there is no bad blood between the two. Besides that, even Bloom only has good things to say about her because she helped him out when he was facing a difficult time in his life. We are always happy to see that not all Hollywood couples have a strained relationship after breaking up. Later on, Bosworth went on to marry Michael Polish in 2013, and they got divorced in 2021. She has been rumored to date Justin Long since then.
Rashida Jones And Mark Ronson
Jones and Ronson began dating, and they were also engaged at one point before they decided to split. Their entire relationship lasted a year, and he proposed to her on her 27th birthday. We still don’t know why they broke up because we only know that things were not working out between them. Of course, we understand why Jones would be attracted to Ronson, as he is one of the top music producers of his time. If you have heard Valerie and Uptown Funk, you know who he is. Jones is now married to Ezra Koenig as they have been together from 2015 till now.
Jenna Dewan And Justin Timberlake
Jenna Dewan and Justin Timberlake began dating in 2002 when she appeared when his music video of Cry me a River. During this time, Timberlake had gotten out of a relationship with Britney Spears. The relationship between Justin and Jenna was short-lived, as they were friends and decided to begin hooking up. We still don’t know how long after breaking up with Britney, he began hooking up with Jenna. According to her, she was not the rebound after Britney, even though it may seem like it. Later on, Jenna went on to marry Channing Tatum for ten years before parting ways with him.
Rozonda Thomas And Usher
Usher and Rozonda Thomas dated for two years after they met when she starred in some of his music videos. Unfortunately, Usher was cheating on Thomas, and she had heard many rumors about it. At first, she did not pay attention because both of them loved each other very much. However, she finally decided it was time to confront the rumors about his infidelity. She finally did, and Usher admitted that he did cheat on her. Of course, they broke up after that, and we are happy that she got out of it when she found out about his infidelity.
Shalane McCall And Brad Pitt
Brad Pitt and Shalane McCall dated for a year when she was only fifteen years and he was twenty-four. Yes, this relationship was not approved by many people as she was a minor back then. A year after they broke up, McCall went on to marry Trent Valladares when she was only 17 years old. They have a successful marriage, and McCall has retired from show business since then. However, she is working and living in Southern California currently. Not everyone likes to stay in show business, and we hope that McCall found her calling after having a short-lived Hollywood career.
Jack Antonoff And Scarlett Johansson
Scarlett Johansson and Jack Antonoff went to prep school together. It was a prep school for children that wanted to become dancers and actors. During this time, they dated for at least a year and even attended their prom together. They began dating around 2001, and they broke up a year later, in 2002. Of course, they were young back then, and their relationship was untimely, which is why it did not last for very long. Both of them have come a long way since then, as Johansson is one of the top actresses of our time.
Tyra Banks And Seal
Seal and Tyra Banks were together on Ghost Whisperer, and during this time, they dated for at least a year before calling it quits. Most people don’t know about their romance because they keep it under the radar. Besides that, Seal went on to marry Heidi Klum, and their marriage lasted for nine years before they got divorced. On the other hand, Banks did not marry anyone, but she has had a very successful career. We are happy for her as she is still taking the modeling industry by storm. The relationship between Seal and Klum is also strained since their divorce.
Michael Cera And Aubrey Plaza
Aubrey Plaza and Michael Cera began dating in 2010, and they dated for more than a year. Even though they broke up, they were in love when they were together. That is because the couple almost got married as they drove across the country after shooting a movie. After they broke up, Plaza moved on quickly as she started going out with Jeff Baena. Ever since then, the couple has been together, and Michael Cera is out of the picture. We hope that they are happy even if they are not with one another during this time.
Dennis Rodman And Madonna
Many people don’t know that Madonna and Dennis Rodman dated each other because their relationship only lasted for two months. Rodman also went on to say that Madonna offered to pay him twenty million dollars for making her pregnant. According to him, she also called him once long-distance to let him know that she had her ovulation period going on. Their relationship did not last because Rodman always thought that Madonna saw him as an object or a kid in a candy store. She thought he was very attractive, which is why she wanted to have his baby. Of course, we don’t know the other side of this story.
Sandra Bullock And Ryan Gosling
Ryan Gosling and Sandra Bullock met when they were filming the movie Murder by Numbers. One of the top reasons their relationship caught the attention of everyone was because they had an age difference of 16 years. Despite that, the couple dated one another for two years before splitting up. During that time, they did not make the reason for their split public. However, later on, Gosling went on to state that the show business made it difficult for them to be together. Both of them have moved on to bigger and better things since then, and we are happy for them.
Jared Leto And Cameron Diaz
Cameron Diaz and Jared Leto dated for four years between 1999 and 2003. There were also rumors during this time that they had been engaged, but this was never confirmed by any of the stars. After four years of dating, the couple decided that it was best to go their separate ways. Ever since then, Diaz has had a long string of relationships, as she dated Alex Rodriguez, Justin Timberlake, and many others. Finally, she decided to settle down as she got married to Benji Madden. We are happy for her because she was not very happy with Jared Leto, as he was not too nice to her.
Taraji P. Henson And Lamar Odom
Khloe Kardashian is not the only star that Lamar has dated, even though their relationship made the headlines for a long time. The couple was dating in 2009, and in the same year, he also got married to Khloe Kardashian. There is also a rumor that Odom proposed to Taraji before he also proposed to Khloe. Yes, their history is incredibly confusing, and Lamar is known for not having the greatest track record when it comes to women. This is why he and Khloe Kardashian also split. He met Henson in 2009 at an HBO party, and they connected instantly.
Alex Rodriguez And Kate Hudson
The basketball star, Alex Rodriguez, has a colorful dating history because he has dated many incredible stars. In his long list, you will also find Kate Hudson, who he dated for seven months. During their relationship, you would find Kate Hudson attending a lot of his games and supporting him throughout. Since then, Rodriguez and J-Lo have dated for four years, and they have a lot of shared projects with one another. Even though the couple has also split, they are also still friends and business partners. We hope Rodriguez finally finds someone to settle down with after such a tumultuous history.
Mandy Moore And Wilmer Valderrama
Mandy and Wilmer began dating when she was only sixteen years old, and they dated for a year. According to Valderrama, he took her virginity when they were dating, and he told this to Howard Stern. However, a year later, Moore had an interview with Elle Magazine and called out Valderrama for lying about these things.Of course, we don’t know what the truth is, but Valderrama has had many high-profile relationships. On the other hand, Moore decided to settle down with Ryan Adams. Later on, the pair also got divorced, and Valderrama never married anyone during this time.
Selena Gomez And Nick Jonas
While they were still Disney kids, Nick Jonas and Selena Gomez dated for a few months before they went their separate ways. They have come a long way since then, as Nick Jonas is now happily married to Priyanka Chopra. On the other hand, Gomez has had a lot of on-and-off relationships with many stars. The split between the two was amicable, and many people also asked Selena about Nick’s sexuality. However, she is still good friends with the Jonas Brothers, and we are happy for them. Gomez is still yet to have someone long-term.
Cher And Tom Cruise
Many people have forgotten that this romance took place, but we are here to remind you again. Cher is sixteen years older than Cruise, and they dated when she was 38, and he was only 23. If you are wondering how they met, then it is when they met at the wedding of Sean Penn and Madonna. Of course, the relationship between these two did not last long, as they only got together for a short fling. She admitted to their fling on Andy Cohen’s show. Besides that, she also considers Cruise as one of her top five in bed.
Justin Timberlake And Alyssa Milano
In 2002, Justin Timberlake and Alyssa Milano dated for a short period of time before eventually parting ways with one another. After that, Justin Timberlake went on to have a long-term relationship with Cameron Diaz. Of course, even that did not last, as he is now happily married to Jessica Biel. Milano was really happy that she bagged Justin Timberlake during that time, as he had always been a heartthrob. She lived the dream of many of us, and we love that for her. Later, she also went on to share a throwback picture of her, Britney Spears, and Justin Timberlake.
Danny Boyle And Rosario Dawson
Danny Boyle and Rosario Dawson dated one another after they met when she was working on Danny’s film Trance. However, they never publicly admitted that they dated one another, which is why they also didn’t announce the split. Their relationship was short-lived because they did not work out as a couple in many aspects. Dawson was the one that made the first move as she was attracted to Danny Boyle. She also went on to make it clear that they did have a lot of common ground with one another. Unfortunately, that wasn’t enough to make them stick for long enough.
Julie Bowen And David Spade
Sometimes, people can be really good friends, but they don’t live up to being good significant others. That was the case between Julie Bowen and David Spade, as she felt that Spade was not a good boyfriend but a great friend. Even though they split, she still sometimes talks to Spade because they are better off as friends. Bowen discussed these details with Justin Long when she was on her podcast known as Life is Short. The couple dated for a year, and most of their relationship was also long-distance. Of course, that never works out, no matter how much you try.
Keira Knightley And Jamie Dornan
If there is one popular actor on TV, then it is Jamie Dornan, who starred in Fifty Shades of Gray. Dornan dated Knightley for two years, and during this time, he was known for his modeling career. Even the pair met one another when they were shooting for an ad campaign, and they instantly clicked. Not many people knew about their relationship, as they kept it low-key. However, Dornan was open about the split when they broke up. He also felt that one of the top reasons for their split was because of incredible fame Knightley had.
Emilia Clarke And Seth Macfarlane
Seth and Emilia dated one another for six months before they decided to part ways with one another. Of course, it is incredibly difficult to picture that the Mother of Dragons would date Macfarlane, but we all make unique choices when dating. She was also titled the Sexiest Woman Alive by Esquire.If there is one person that has missed out, then it is Seth Macfarlane, as Clarke is one of the most sought-after women in Hollywood. The reason that they split was that they could not continue doing long-distance. Distance does not always make the heart grow fonder.
Chelsea Handler And 50 Cent
Chelsea Handler admitted that she dated 50 Cent for a short while on Oprah’s show. According to her, his public persona is completely different from who he is in real life, which made the star fall in love with him. However, they split after a short while because they had a dispute over Ciara, his ex. At one point, Handler even stated that she would never date a guy whose name is a number. Of course, that was not the case when dating 50 Cent, as she decided to set that rule aside. While they dated, Handler was swept off her feet.
Sean Penn And Scarlett Johansson
During the spring of 2011, Sean Penn and Scarlett Johansson had a romance going on as they were spotted on many dates throughout Los Angeles. Many people did not approve of this pair because of the incredible age gap between the two, as they were twenty-four years apart. However, their relationship only lasted a few months. Both of them did not talk about their relationship for a long time after breaking up. However, Johansson did admit to seeing him for a while and spending time with him. She did not get into any other details about dating Sean Penn.
Brad Pitt And Christina Applegate
Brad Pitt is still one of the most attractive men in Hollywood, and rightly so. This is why we can’t blame Christina Applegate for adoring him and dating him, even if she broke up with him later on. However, halfway through her night with Pitt, she ditched him for someone else. Andy Cohen asked her who the man was during his Plead the Fifth segment, and Applegate did not reveal the identity of the man. The most shocking thing is that she didn’t even date the man she left Pitt for. Of course, Brad and Christina didn’t get together after this incident.
Carmen Electra And Simon Cowell
Carmen Electra was attracted to Simon Cowell because she thought he was really fun to be around, charming, intelligent, and much more. However, they split up because Cowell was not loyal to their relationship. Now they are just friends, as they split amicably without any hate towards one another. Electra found out that he had a romance with Lauren Silverman, who even carried the child of Cowell as she got pregnant during this tryst. Even after everything, Electra tells everyone that she thinks Cowell will be a fantastic father. We love the grace with which she handled the breakup.
Kirsten Dunst And Jake Gyllenhaal
Jake Gyllenhaal has always been a heartthrob, as he is one of the most good-looking stars in Hollywood. Dunst and Gyllenhaal dated for two years before they decided to split and break the hearts of their fans. According to Dunst, one of the top qualities that drew her towards Gyllenhaal was that he is an exceptional actor. They were good while they were together, but they eventually split up because their lifestyles were incredibly different. Gyllenhaal likes to stay home, while Dunst likes going out a lot, and she is an extrovert. They decided that it was best to part ways and live life their own ways.
Owen Wilson And Sheryl Crow
Sheryl Crow and Owen Wilson dated for two years before they called it quits. Both of them met when they were playing a part in the movie known as The Minus Man. After that, Crow went on to get engaged to Lance Armstrong, but even that did not work out for her. Crow and Wilson were incredibly public with their relationship, and you would see them everywhere when dating. However, it all eventually faded away, and the stars parted ways. Even her engagement and relationship with Lance Armstrong faded away after three years of dating, and now she is single as men have failed her.
January Jones And Ashton Kutcher
Ashton Kutcher has had a colorful history in the world of history, and we don’t blame him. At one point in time, he was also dating January Jones, and their relationship lasted for three years. We still don’t know how they met, but they were serious with one another while they dated.
After they broke up, Jones did not take a lot of time to move on, as she began dating Josh Groban. They also dated for three years before breaking up. Of course, Kutcher is now married to his co-star in That 70s Show, Mila Kunis, and they are incredibly happy together.
Chris Evans And Jessica Biel
Jessica and Chris have a very tumultuous relationship because they dated on and off for five years. At one point, they were so in love that they also discussed marrying one another. They also discussed having children and other things that come with the territory of being a married couple. However, that never came to fruition, and Jessica met Justin Timberlake after her breakup with Chris Evans. Of course, the rest of it is history as she finally found her soul mate and the person she wanted to marry. We are happy that they are happy even if they are not together.
Luis Miguel And Mariah Carey
Mariah Carey and Miguel dated for three years, and according to her, she only has significant relationships in her life. She met Miguel when her divorce proceedings from Mottola were still going on. Her marriage did not last very long and well, and she called Mottola a controlling figure. Carey also states that Luis Miguel was an authentic lover, but they parted ways after three years of dating due to many reasons. They even recorded a song with one another, but Miguel did not like it, which is why it never saw the light of day, and rightly so.
Joey Fatone And Pink
Did you ever dream of being with an NSYNC member during the early 2000s? Well, almost all girls had this fantasy, and Pink took one for the team when she began dating Joey Fatone. Both of them remember things differently, as Pink told everyone that he was in love with her and took her out for ice cream. On the other hand, Joey Fatone recalls that Pink friend-zoned him during that time. Whatever it was, we do know that they had a short fling that did not amount to much. However, we are excited that both of these superstars got together at one time.
Kim Kardashian And Nick Lachey
Kim Kardashian is known for not having very long relationships, and even the one with Nick Lachey was a short-lived one. Because of this, Lachey states that it would be a bit of a stretch to say that they were dating. However, they did go out to watch a movie more than ten years ago, and the paparazzi swarmed them during this time. He said this when Andy Cohen asked them about their relationship on his show. Lachey is smart, and he thought that other things were in play when so many paparazzi swarmed them during their movie date. They have not been in touch since then.
Janet Jackson And Matthew McConaughey
The rumor that Janet Jackson and McConaughey were dating was a long one, and no one had the guts to set the record straight. However, Andy Cohen was determined to take on this task during Watch What Happens Live. Of course, Matthew knew better than to admit it, which is why he laughed off the question. However, Cohen is also unstoppable, and he kept pressing McConaughey about the question. Finally, he did admit that they went on a date as they got together for dinner, and that was it. If there was more, at least he did not admit it on the screen.
Lucy Liu And George Clooney
George Clooney and Amal are one of the hottest couples we know of right now, but before they got together, Clooney dated Lucy Liu. She is one of the angels from Charlie’s Angels, as she is famously known for this role. Kudos to her for bagging the most eligible bachelor in Hollywood, even if it was short-lived. They were dating at the beginning of 2000, but this rumor was never confirmed. However, they were seen canoodling in the car multiple times. So, of course, we have good reason to guess they dated, but they kept it on the down low.
Liam Neeson And Julia Roberts
Julia Roberts and Liam Neeson are both fantastic superstars that have come to Hollywood. Of course, this is why we have to keep track of who they are dating, and both of them were together at one time. They used to date before they got married to their soul mates, and many people have forgotten this little fact about the couple. However, their relationship lasted for a good two years before they parted ways. The stars met on the set of Satisfaction and instantly clicked. Finally, after two years of dating, they decided it was time to explore other options.