Hollywood Pairs That We Forgot Were An ItemBy Jonathan K
We all get so caught up watching the glitz and glam of the celebrity world that we can sometimes forget they are people too. Sure, they have their fancy houses, private chefs, and town cars, but when it comes to dating and marriage, boy, do they have it harder than us. Some of them go through dates so fast, it’s impossible to keep up. We’ve listed down couples that were once an item and trust us when we say the list will either surprise you or have you going “Oh Yeah! I remember that!” Waltz down memory lane with these memorable duos, and remember: love takes a lot of effort and it’s easy to file for a divorce. Staying in a marriage is even harder. Kudos to these couples that tried and awesome job to the ones that stayed.
Joaquin Phoenix and Liv Tyler
Joaquin Phoenix has recently made a whole new image for himself and made a huge comeback as the Joker. He was lauded when the film came out and of course rumors and questions began to circulate: who did and who is Joaquin Phoenix dating?
Well, since he is a low key kind of guy, there’s not much known about his dating life in general. However, we do know that he used to date Liv Tyler and while the relationship did not work out, Liv mentions that she considers Joaquin and all his sisters to be like family to her.
Madonna and Michael Jackson
When this musical duo got together it was as though the musical world imploded! When the Queen of Pop and the King of Pop are getting together, what could possibly rock the world harder? Fans worldwide were shocked when they attended the Academy Awards together.
However, everyone was also wondering if it all was just a plot for Madonna’s documentary, Truth or Dare. Well, regardless of that, it was definitely a red carpet moment for everyone when they walked together! And while the magic of possible romance did not last, the pair remained friends for the rest of Michael’s life.
Tom Cruise and Penelope Cruz
Apart from his myriad of action movies, this movie star is also known to date and marry a lot. In fact, he was married three times and let’s just say none of those relationships was kept low key. No shocker there, Tom Cruise is one of the biggest Hollywood heartthrobs of the past few decades.
Soon after his divorce from Nicole Kidman, Cruise found himself enraptured by Vanilla Sky co-star Penelope Cruz, who he met dated for three years before finally breaking it off in 2004. Of course, after that, he married and divorced Katie Holmes. That must have been a lot of wedding rings down the drain.
Angelina Jolie and Jonny Lee Miller
The whole world knows about Angelina Jolie and Brad Pitt (and the drama that went down with Jennifer Aniston), but what not many know is that long before she got the attention of Pitt in Mr. & Mrs. Smith, she once caught the attention of another co-star, Jonny Lee Miller.
They met on the set of Hackers in 1995 and married a year later. Sadly, after only 3 years, the marriage ended. Angelina Jolie is one of those timeless stars that we’ll always remember, so this little fact might be new news for you!
Busy Philipps and Colin Hanks
This former couple is honestly the epitome of how healthy breakups should be, and also how strong friendships are born. When Busy Philipps and Colin Hanks (yes, the son of good guy Tom Hanks) met, they decided to date for about a year before deciding they should be friends instead.
Unlike others who say “we should stay friends”, these two actually did remain really good friends and even go on holidays with their spouses. Talk about being friends with your exes! Seems like this pair really knows how to let bygones be bygones.
Edward Norton and Salma Hayek
Here’s another dating fact about Edward Norton. He used to date Salma Hayek and they made a pretty good looking couple! The fun part here is how they met. Out of all places to happen upon each other, they met at a clinic and developed their relationship there.
It wasn’t like how other celebs met like on set or at a party: these two apparently shared the same chiropractor and ended up meeting at the clinic often. To be honest, this love story is so much better than a regular ol’ celeb hookup. It’s far more relatable.
David Arquette and Drew Barrymore
This couple is confusing because there is a lot of he said, she said going on. David Arquette and Drew Barrymore worked together on Never Been Kissed and while Barrymore denies the rumors, Arquette seems to have a whole other understanding of their relationship.
He even says that they dated long before they even worked on the movie. Regardless of who is right or wrong, one can’t resist noticing the spark between this iconic duo. Not only are they beautiful people together but individually they’re both incredibly talented.
Shia LaBeouf and Hilary Duff
Here’s another Disney relationship that most of us didn’t know actually happened. As a matter of fact, there’s a high chance that we did see the photos of them together growing up and assumed that Even Stevens and Lizzie McGuire were just hanging out.
Ah, the good old days of naivety. Well, they were in fact dating for a period, and sadly, they did not match at all. Shia LaBeouf even said that it was “probably the worst date either of us has ever had”. At least our Disney fantasies have been fulfilled.
Brooke Shields and Nicolas Cage
The Hollywood ‘It Girl’ with a controversial dating track record, and a bad boy with a history of ending relationships on a disastrous note, found themselves dating one another for a very short amount of time — which was approximately two months.
When Brooke Shields and Nicolas Cage got together, lots of fans were only waiting to hear the news of their breakup because they had assumed when two people with that kind of dating history get together, it can only spell disaster. And they were right.
Zooey Deschanel and Jason Schwartzman
Zooey Deschanel has made quite a name for her being the quirky fun-loving heroine in most of her movie — with the exception of 500 Days of Summer, which, let’s be honest, made more than a few of us feel sad and lonely. We’ll never forget Zooey’s role as Summer, and all the hearts that she broke.
However, when she got a supporting role in Almost Famous, she got to know and started dating Jason Schwartzman in 2003. The couple were out of the whole paparazzi craze as they kept their relationship low key, and ended up parting ways in 2005.
Courtney Love and Edward Norton
This duo may not be a pair everyone remembers. We all know rock leading lady Courtney Love as the late Kurt Cobain’s wife. However, before these two settled down into what would become one of modern music’s most famous relationships, Courtney Love was dating Edward Norton.
The pair met on the set of The People vs. Larry Flynn and soon started dating. The two dated for a long 5 years and even got engaged for about 6 months before they decided to end the relationship. Even if it didn’t last, they certainly do look great together.
Jennifer Love Hewitt and Will Friedle
Jennifer Love Hewitt was every teen boy’s and some grown men’s fantasy. She was considered an extremely hot woman and was wildly popular in her era, which can be proven in some of her movies like I Know What You Did Last Summer and Trojan War, where she met Will Friedle.
While Will was not exactly the kind of guy you’d think Hewitt would go for, they did make a cute pair. Will was known for his work as the voice of Ron Stoppable in the Kim Possible series. This sweet duo was a match made in heaven but unfortunately, they didn’t last very long.
Miley Cyrus and Nick Jonas
Disney relationships are cute to look at but are supremely complicated and before you know it, it’s like everyone is dating each other! Nick Jonas once used to date Miley Cyrus back in 2006 and it was hailed the biggest Disney romance there is.
Unfortunately, it ended only after a year. While Jonas went on to dating other women, Miley mentioned that it took her some time to get over it and took some time off to truly find herself and figure out who she is. Miley went into many other doomed relationships afterward, while Nick Jonas married Priyanka Chopra.
Tyra Banks and Drake
While the two deny they actually dated, we’re going to put this into our list because even going on one date counts here! Drake (aka Aubrey Graham) and Tyra Banks sorta-kinda used to be together for a day. The chemistry is totally there, and so we wonder why they didn’t continue their relationship.
But it’s so cute that they actually went to Disneyland for that date! They disguised themselves and had a fun day at the park. And while Drake did mention that it was more like a get-together, we’re sure some sparks flew. And if they didn’t, then allow us to wallow in our fantasies just a bit longer.
Luke Wilson and Gwyneth Paltrow
Luke Wilson is an understated actor, and not many remember his dating life when compared to his arguably more extroverted brother Owen Wilson. However, these are the exact traits that led Gwyneth to date the youngest Owen sibling. What a sweet couple!
She stated in an interview that he was someone who was “well educated, funny, witty, artistic, and has a lot of integrity. He doesn’t have to grab all the attention in the room”. She also made sure to note he’s “a good kisser”. Well, we believe her! His acting itself shows he’s a man of talent and taste.
Jennifer Aniston and Paul Rudd
This is a pairing that we could not imagine at all, mainly because we are fans of the sitcom Friends and seeing Rachel and Mike together. It’s weird to think that even in an alternate universe Rachel and Mike could be together, but then again this is real life and we can only wish that Friends was real.
While Jennifer and Paul’s romance did not last very long, they remained good friends and even joked about having to do kissing scenes with each other. Talk about professionalism. It’s more than can be said about some of the former couples on this list, and by a long shot.
Anjelica Huston and Jack Nicholson
It’s no secret that Angelica Huston has had a pretty complicated life. From dating someone who was 23 years her senior to dating someone who had assaulted her and even being a witness to the Roman Polanski case, her love life in her heyday could be described as chaotic.
But when she had dated fellow screen star Jack Nicholson, it became even weirder. She dated and lived with Jack on and off until it was announced that he had gotten another woman pregnant. Now, that’s a soap opera in the making.
Zachary Quinto and Jonathan Groff
Star Trek actor Zachary Quinto and Glee actor Jonathan Groff used to date and they made a gorgeous pair! While their relationship did not last long, reportedly due to issues associated with being long-distance, Quinto spoke so highly of Groff, even stating that he found his soulmate in Groff.
Quinto also mentions how incredibly lucky he was to have had Groff in his life after a series of unfortunate relationships. If only they had worked out! We loved Zachary Quinto in American Horror Story and can only hope that he keeps up the amazing work at being an actor.
Bradley Cooper and Renée Zellweger
Bradley Cooper is a dreamboat and the ideal guy for a lot of people out there. He has been happily off the dating scene since 2015. However, before meeting his current girlfriend, who gave him a child, he dated Renée Zellweger.
Their romance was very low key and though the media was relentless in finding out if the pair really were an item, they always refused to answer. Come 2011, their relationship ended. The two were stealthy enough to keep their relationship a secret but the media just couldn’t stay away from this irresistible pair.
Cindy Crawford and Richard Gere
While having a partner to love and hold in spite of all their flaws is a wonderful and rare thing, sometimes we have to be more realistic. Take this couple, for example. Cindy Crawford and Richard Gere had a large age gap that both didn’t take into account before eloping.
Crawford was only 22 and Gere was 39 when the pair decided to elope. The romance lasted for 4 years before they called it quits. Maybe the age difference played a role, but there are so many other factors that need to be taken into account.
Rachel McAdams and Michael Sheen
It’s safe to say that whoever dates Rachel McAdams got really lucky. She has come a long way from her Mean Girls days as Regina George, and has blossomed into a versatile actress who is somehow able to cry and be sopping wet and still look stunning.
Michael Sheen probably agrees with us. Though they dated for 3 years before breaking it off, Sheen speaks very fondly of the actress, saying how she always keeps him laughing. It’s nice to see a couple who can still remain civil even after a breakup.
Matthew McConaughey and Janet Jackson
This pair did not actually turn things into a full-blown relationship. Sure, they went on one or more dates, but they didn’t date exclusively. Apparently, the media was in a frenzy on whether or not Matthew McConaughey and Janet Jackson were actually an item.
Well, show host Andy Cohen obviously could not take the pressure anymore, and decided to drill McConaughey on the subject. The actor finally caved and fessed up that they just went on a date, had dinner, and that was about it. Sorry guys, no more juicy details.
Julia Roberts and Liam Neeson
Watching our fave actors date each other is pretty cool. It’s like watching the fictional characters on your best beloved TV show that you’re rooting for come to life and date each other. This next couple is a match in heaven because of how iconic the members of this duo are individually.
When Oscar-winning actors Julia Roberts and Liam Neeson dated, they certainly seemed like a bona fide golden couple. They met on the set of Satisfaction and fell for one another but alas, the relationship didn’t last. They dated from 1988 to 1990.
George Clooney and Lucy Liu
Ah yes, George Clooney. The ever-elusive, most wanted bachelor at his prime. A lot of female celebrities were vying for his attention, and while he did date a lot, he never did settle down with any of them, until he met the ever-beautiful and intelligent Amal Alamuddin. And as we all know, she managed to tie the actor down.
So before Amal, came along, Clooney had dated Charlie’s Angels star Lucy Liu however, it was never confirmed how long they dated. The two make a stunning pair but unfortunately, they didn’t last either. Trivia fans will remember that Lucy Liu had appeared briefly on Clooney’s breakout show, ER.
Sheryl Crow and Owen Wilson
When you think of who Sheryl Crow is dating or at least who she was dating, you often think of Lance Armstrong. And while her engagement to the world-renowned cyclist was a pretty popular one, she actually used to date Owen Wilson from 1999 to 2001.
They had met on the scene of a little-seen film called The Minus Man and sparks flew. Ever the artist to keep her music as real as possible, Crow has even dedicated a song called “C’mon, C’mon” to Wilson on account of their relationship.
Nick Lachey and Kim Kardashian
Nick Lachey was a ’90s teen heartthrob that likely had his posters hung in man teen girls’ rooms. He was a former member of the famous boyband called 98 Degrees. Clearly, Kim Kardashian thought he was dreamy as well, and they dated for a short period of time.
However, while the relationship did not last, Lachey recalls his time with the reality star as being very surprising, as he witnessed the extent of her fame through how the paparazzi were around her all the time. After all, even if you’re a pop star, expect an unbelievable amount of press coverage if you’re going out with a Kardashian.
Mariah Carey and Luis Miguel
The relationship between Mariah Carey and singer Luis Miguel is immensely hard to delve into, as Luis was a fiercely private person and rarely gave out interviews regarding his personal life. What we do know is that the two dated from 1998 to 2001, having first met at Aspen while on vacation.
They even tried to collaborate on a duet together, but Luis hated the final product so much that he cut up the tape into pieces and sent it back to the producer, David Foster. Seems like Mariah Carey wasn’t necessarily the diva of the relationship!
Ashton Kutcher and January Jones
Remember who Ashton Kutcher used to date? Nope, we’re not referring to Demi Moore, nor his current wife and former co-star, Mila Kunis. So who else? We can’t really remember either. Because of his two high profile relationships, everything else sorta fades out.
Anyway, here is a little refresher: Kutcher actually dated actress January for three whole years! That’s a pretty steady relationship for us to have forgotten about it. Jones would go on to date such big names as singer Josh Groban and SNL cast member Will Forte.
Pink and Joey Fatone
The relationship between Pink and Joey Fatone of NSYNC may not be one that’s fresh on everyone’s mind, seeing as they only dated for a short period of time. But when we read about what Joey did for Pink, we can’t deny that while it was a short relationship, Joey has got the whole sweeping a girl off her feet thing down.
Pink revealed in an interview that Joey took her to Friendly’s and bought her ice cream. Classic! And to top it all off, he even got Pink’s father’s permission to take the singer out on a date! What a sweet person; it would have been intriguing to see how this could have panned out.
Jake Gyllenhaal and Kirsten Dunst
When Spider-Man hit the cinemas, Kirsten Dunst was everyone’s idol, the leading lady, bombshell, or whatever it is that you call someone everyone wanted to have. And when she starred in Bring It On, well, let’s just say the world raved about all that is Dunst.
Jake Gyllenhaal was one of her admirers as well, and the pair went on to date for 2 years before splitting up in 2004. Sadly, based on an interview Dunst did, she and Gyllenhaal may not have ended things on good terms.
Simon Cowell and Carmen Electra
The big-time music mogul Simon Cowell is known for having dated a myriad of drop-dead gorgeous women, so many that it can get rather hard to remember who they were. Well, here’s a reminder that he once dated Carmen Electra, a former Playboy Model.
Sadly, they only dated a few months, from December 2012 to February 2013, and ended things mainly because Simon was reportedly unfaithful. It’s shocking that it took that little of a time for him to cheat. And to imagine that. he cheated on Carmen Electra! Boy, oh boy.
David Spade and Julie Bowen
David Spade is the George Clooney of the comedic world as E! News describes, and this is strangely true. If you take a look at David Spade’s dating profile, you will see exactly why he has received this rather flattering moniker.
From Carmen Electra to Tara Reid to Pamela Anderson, it seems Spade has rarely found himself without a beautiful woman on his arm. To add to the list, funny man David Spade and eccentric Modern Family mom Julie Bowen once used to date for just over a year, in 2002.
Jamie Dornan and Keira Knightley
The brooding Christian Grey, who was played by actor Jamie Dornan, caught everyone’s attention when 50 Shades of Grey first hit the cinemas. But long before that, Dornan caught the attention of one Keira Knightley in 2003. Side note: we’re absolutely living for Keira Knightley in 2003, she looks absolutely stunning.
At the time, the two were not considered high-profile actors yet, and were not too popular, with both of them doing smaller-scaled movies. However, they have since reached stardom, with Keira Knightley snagging the leading role of Elizabeth in Pirates of the Caribbean. The two parted ways in 2005.
Nick Jonas and Selena Gomez
This is yet another Disney couple that people do not realize, nor remember, dated. Seeing as Selena Gomez had an on-and-off relationship with teen heartthrob Justin Bieber, it’s easy to forget she once dated yet another wildly popular teen dreamboat, Nick Jonas.
While keeping up with Selena’s dating life is a bit difficult, Nick has managed to land one of the most intelligent and gorgeous women in the world, Priyanka Chopra. Looks like Selena was a pivotal part of his life, but he eventually found his queen.
Rosario Dawson and Danny Boyle
Sometimes being a celebrity is harder work than it seems. People watching your every move and judging your every action regardless of the story behind it can be why a lot of celebrities dodge questions about their love life like bullets. So when Rosario Dawson and Danny Boyle started in 2013, it was mostly speculation.
They would look like they were more than friends, but would deny dating. Finally, rumors were buzzing yet again that they had broken up. Rosario mentioned once that: “It’s not like we announced our relationship, so it’s not like we’re going to announce our breakup.”
Alyssa Milano and Justin Timberlake
The story of Charmed star Alyssa Milano and Justin Timberlake is quite cute, and we’ll tell you why in a bit. First, some tea: when Justin Timberlake dated Jenna Dewan, she had insisted she was not a rebound from JT’s failed relationship with Britney Spears.
And then along came Alyssa Milano. The cute fact here is that while their relationship did not last long, JT actually had a crush on Milano growing up and even had posters of her hung on his wall — and was able to be by her side in real life, if only for a fleeting moment.
Kate Hudson and Alex Rodriguez
Kate Hudson will always hold a special place in ladies’ hearts because she had taught us exactly how to lose guy in 10 days. But clearly she also knows how to get a guy in the first place, because long before baseball star Alex Rodriguez was dating Cameron Diaz, Madonna, or even J.Lo, he was dating Kate.
Their relationship did not last very long; in fact it only carried on for about 7 months before they called it quits. But let’s put that in perspective for a second: in the Hollywood dating world, 7 months seems like a long time for most couples. So kudos to them!
Tom Cruise and Cher
Cher’s marriage and professional career with Sonny Bono was the talk of the town, and we all know how Cruise’s relationships with Nicole Kidman and Katie Holmes turned out. But who among us can remember that once upon a time, this pop diva and action king were an item?
It was a hot topic that was trending for years to come. So if you didn’t know that Tom Cruise and Cher were once a couple, you’re welcome! Their relationship didn’t last very long, but we’re here for this age gap: Cher is sixteen years Tom Cruise’s senior.
Lamar Odom and Taraji P. Henson
Usually, when someone is linked to the Kardashians, it’s hard to think of them as their own entity. So seeing Lamar Odom as an individual without having Khloé Kardashian’s name plonked beside him is a bit of a surprise. But yes, this ball player has a love life of his own.
Lamar Odom and actress Taraji P. Henson dated before Odom moved on to Khloé, and while Lamar’s proposal to Khloé was sweet and all, just a few weeks before popping the question, he actually asked Taraji first — and she turned him down. Yikes!
Cameron Diaz and Jared Leto
Cameron Diaz is everyone’s favorite quirky heroine, with a big laugh and a heart just as big as her smile. While she doesn’t have the best dating track record, she has managed to date some pretty high profile men, like Jared Leto. After all, she is Cameron Diaz.
She and Leto dated from 1999 to 2003, and there was even a rumor that they were once engaged, because Diaz was seen wearing a huge engagement ring worth $15,000 to the Golden Globes in 2003. Sadly, it was the same year they broke up.
Wilmer Valderrama and Mandy Moore
The voice actress of Rapunzel in Tangled once got together with Wilmer Valderrama from That ’70s Show and they were a lovely pair indeed. Obviously the relationship did not last, ending after just about a year of dating — which, however, is a long time in Tinseltown.
They dated from 2001 to 2002, before Moore went on to date Scrubs star Zach Braff in 2004. She settled down with husband Ryan Adams, before divorcing in 2009. Wilmer, however, has not married yet. Moore was reportedly hurt by Valderrama telling the press just a bit too much information about their relationship.
Madonna and Dennis Rodman
The dating scene in Madonna’s life has been nothing short of controversy and juicy gossip for tabloids everywhere. We all know the whole Madonna and Guy Ritchie drama that unfolded before our very eyes. But long before Ritchie, she had dated flamboyant basketball player Dennis Rodman.
While the Ritchie story got everyone riled up, in a recent interview Rodman said that Madonna had allegedly offered him $20M to get her pregnant. Their relationship only lasted 2 months, so we do wonder how that deal even got on the table.
Seal and Tyra Banks
The marriage of Seal and Heidi Klum is one that was raved about, highlighted in the press as the epitome of a wholesome modern celebrity marriage. So it’s of no surprise that when the marriage ended, fans everywhere were crushed. The iconic duo was quite popular on social media with their pictures strewn everywhere.
However, before dating Heidi, Seal was actually enraptured by another familiar model, none other than Tyra Banks. Their relation was very brief which is why not many people knew they dated. But in the ’90s, both were among the biggest names in their respective fields.
Aubrey Plaza and Michael Cera
These two were like the perfect comedic duo, and seeing them together in real life made people wonder if they just laughed in each other’s presence all the time. They met on the set of Scott Pilgrim vs. the World and sparks flew.
Sadly, they only dated for over a year before breaking up. Aubrey spoke in an interview about Michael, reminiscing about how they drove across the country and almost got married in Vegas. They’d make an adorable couple, though Aubrey seems too feisty for Michael.
Justin Timberlake and Jenna Dewan-Tatum
We all loved Jenna Dewan and Channing Tatum together! They looked good together and when they spoke about each other in interviews, it was clear they were couple goals. Plus, it was rare to see a Hollywood romance that lasted as long as they did, seeing as they were high profile celebs.
But before meeting Tatum, she once dated Justin Timberlake, and what’s more, it was around the same time when JT broke up with Britney Spears. It’s no surprise, since the pair love dancing, and maybe that’s one of the reasons why they had a blossoming relationship.
Michelle Rodriguez and Zac Efron
When news broke out that Michelle Rodriguez and Zac Efron were dating, a lot of people, fans and casual observers alike, said they were not a good match. This was mainly due to their 10-year age gap, where Rodriguez was significantly older.
Weirdly enough, they only dated for 2 months, but after they broke up, Rodriguez started a relationship with the model Cara Delevingne the same year. This brought up the speculation that maybe it wasn’t a usual breakup between the former couple.
Usher and Rozonda “Chilli” Thomas
Usher and Chilli were huge back in the early 2000s, and when they got together it was the formation of a power duo. Plus, with their singing careers skyrocketing, their popularity only grew to greater heights when the news of their relationship got out.
Sadly, like most celebrity relationships, it died down pretty soon. They dated from 2001 and broke up in 2003. Rumors said it was because of Usher’s infidelity, but Thomas said that it was just the passage of time. Whatever reason it may be, the two were a cute pair while it lasted.
Orlando Bloom and Kate Bosworth
Everyone is currently buzzing with the news of Pirates of the Caribbean star Orlando Bloom and Katy Perry having their first child together. But long before the popstar, not to mention Victoria’s Secret model Miranda Kerr, the heartthrob was in a relationship with Kate Bosworth.
Their relationship lasted for about two years, as they finally called it quits in 2005. Clearly Orlando did not have any trouble finding gorgeous women to date after Bosworth. She, in turn, found love with director Michael Polish, and the pair have been wed since 2013.
Jennifer Garner and Scott Foley
There’s no denying that Jennifer Garner is a sweetheart, which is why her divorces got a lot of her fans sad and surprised on her behalf. However, before her highly-publicized relationship with Ben Affleck, she was dating and later married Scott Foley.
They had met on the set of Felicity and sparks flew, but their marriage was fated to only last 3 years. In an interview, Garner reportedly said that they did have a shot, and while Foley was a great guy, their relationship together just imploded.
Ben Affleck and Gwyneth Paltrow
Before Brad Falchuk, before Chris Martin, Gwyneth Paltrow was dating Ben Affleck. That’s right, remember them? They used to be an “it couple” because of how awesome they looked together — not to mention she nabbed an Oscar at that time. They called it quits after two years of dating.
And while they did get back together briefly, they finally decided to put the relationship to rest in 2000. Paltrow mentioned in an interview that while Affleck was a nice guy, he just wasn’t ready to have a girlfriend. Ouch.
Sarah Jessica Parker and Robert Downey Jr.
These two actors played roles that were deeply loved by the world: Sarah Jessica Parker as Carrie Bradshaw and Robert Downey Jr. (albeit much later on) as Iron Man. However, before Parker met her current husband, Matthew Broderick, she was dating Robert.
They dated for 7 years before ending it in 1991. The reason for their relationship not working out was apparently due to the fact that Downey was struggling with his addiction at the time, and it would take him roughly a decade of recovery.
Cameron Diaz and Justin Timberlake
Did you know that the Charlie’s Angels star Cameron Diaz and Justin Timberlake used to date? The pair of A-listers dated for quite some time, and Justin even mentioned that their relationship was quite serious and more adult compared to his previous beau, Britney Spears.
They called it quits in 2007 after having dated for about 5 years. Fun fact here is that they actually filmed a movie together 4 years after the breakup, but they said there was no awkwardness at all. It’s refreshing to see ex-couples remaining friends.
Kim Kardashian and Nick Cannon
Pretty sure there’s no human being on earth with access to news or TV who hasn’t heard of Kim Kardashian. From tapes to 72-hour marriages to her union with rapper Kanye West, Kim K has done it all. And she’s also dated a ton of high-profile men in the process.
However, before the world was trying to keep up with the Kardashians, Kim was keeping up with someone of her own: Nickelodeon host Nick Cannon. They dated for a mere four months in 2006, which is probably why not many remember this odd couple. They didn’t seem like they matched, either.
Michael Keaton and Courteney Cox
Everyone knows actress Courteney Cox. We remember her best as Monica Geller, the chef with an OCD for cleanliness. But before she was known for her role as Monica, she was dating Batman star Michael Keaton. The pair were almost a match made in heaven.
A little-known fact here is that they actually dated for 6 years before they finally decided to break up in 1995, a little over a year after she had started doing the show that would make her a household name.
Reese Witherspoon and Jake Gyllenhaal
When Reese Witherspoon’s marriage to Ryan Philippe went down, Witherspoon was in a sad place, as you can imagine, seeing as he is also the father of her children. And that’s precisely why what happened next made fans all over rejoice!
Love soon blossomed between her and the hunky Jake Gyllenhaal, and the two of them together were certainly a sight for sore eyes. They met in 2017 while filming Rendition and the rest was history. Unfortunately, their romance only lasted for two years.
Scarlett Johansson and Sean Penn
There’s a saying that goes that love is blind, and we suppose that age doesn’t matter when two hearts are in love. However, when the age gap is huge, people tend to get rather disturbed and grossed out. But these two celebs managed to carry their relationship well.
In 2011, Sean Penn was 50 while Scarlett Johansson was a mere 26 when they started dating. Seeing as how glaringly big the age gap was, not many were particularly surprised when the relationship fizzled out after just 5 months.
Christina Applegate and Brad Pitt
Here’s something that may shock you. We all know that Brad Pitt was (and for many, still is) a heartthrob. Girls all over the world swooned at Pitt’s beautiful eyes, thick locks, and amazing jawline. He was the man of our dreams when we were young.
So you’d think that any woman who is lucky enough to date someone like Brad Pitt would keep him tightly by her side, right? Well, not Christina Applegate. In fact, she took him as her date to the 1989 MTV Video Music Awards and then proceeded to ditch him for another man! Woah.
Seth MacFarlane and Emilia Clarke
Seth MacFarlane is the comedic genius who served as the brain behind the seminal animated television series Family Guy. A true voice talent, he played so many characters on his own show that it’s hard to tell where his touch stopped and where it began.
On the other hand, we have the lovely Emilia Clarke, who is a bubbly young lady in real life, but played the stern and calculating Khaleesi, Mother of Dragons on Game of Thrones. How their paths crossed is a complete mystery to us. But they did, and their relationship lasted for 6 months.
Kid Rock and Pamela Anderson
Back in the day, seeing Pamela Anderson and Kid Rock in the celebrity news gossip was not a surprising thing. Their relationship was rather tumultuous from its start to its bitter end. The two were both considered pretty wild and “out there” people; no wonder they made a good match at the time.
They dated for quite a number of years, off and on. So when they called off their engagement and split up, people thought “okay, that’s over” — but it was far from over. They soon got married on a yacht in 2006 before getting divorced just a mere four months later.
Alexis Bledel and Milo Ventimiglia
Gilmore Girls had every mother and daughter envying the relationship between Lorelai and Rory, which is why it was a sad time for all when it ended. The two were an adorable couple and Alexis had eyes that could melt anyone’s soul.
Plus, watching Alexis and Milo on screen was made just that much more perfect, knowing that they dated in real life as well. The two started their off-screen romance in 2003 and while they did make a great couple, they called it quits after 3 years of dating in 2006.
Blake Lively and Penn Badgley
Today, Blake Lively and Ryan Reynolds’ relationship is touted in the press and on social media as one of the most obvious examples of couple goals out there. Well before Lively married the Deadpool star, she was once dating Penn Badgley.
Mainly because they were an on-screen couple on Gossip Girl as well, the couple received plenty of buzz. While fans were disappointed they broke up in 2010, there can perhaps be some solace in knowing they ended up staying together on screen.
Ryan Reynolds and Alanis Morissette
As previously mentioned, today, actor Ryan Reynolds’ relationship with Gossip Girl star wife Blake Lively is often praised for how healthy it appears to be. But given his undeniable charms, it’s not surprising that he too has his share of past relationships.
Long before Reynolds met his lovely wife he was actually dating and was engaged to a fellow Canadian, superstar singer Alanis Morissette. After four years as a couple, their courtship fell through and they bid each other adieu in 2006.
Leonardo DiCaprio and Gisele Bündchen
Leonardo DiCaprio is the world’s most famous bachelor, seeing as George Clooney is out of the picture now. The world still watches his dating life to see who he casts as his leading lady, since it’s probably hard to snatch the attention of such a man.
There was a time where supermodel Gisele Bündchen managed to do so. Even though they were a gorgeous couple, the romance was not to last, and the relationship went off and on for 6 years before Gisele decided to marry Tom Brady.
Mila Kunis and Macaulay Culkin
This couple dated for a long 8 years, which is why it’s strange that not many people knew they were once very close. Of course, seeing as Mila Kunis is now married to Ashton Kutcher may make people forget who she was with before.
They dated from 2002 to 2011, and Kunis said in an interview that dating Culkin was like dating a mega superstar, as fans would scream his name and they would be stopped all the time. Can you imagine dating someone as famous as him? Must have been challenging, particularly for an up-and-comer as Kunis was at the time.
Gwyneth Paltrow and Brad Pitt
Long before the drama and intrigue surrounding Brad Pitt and Jennifer Aniston, there was a time where Pitt and Gwyneth Paltrow were an item. They broke up and went on to have high-profile marriages of their own, but in the ’90s, these two were among Hollywood’s ‘it’ kids.
They met while filming the movie Se7en together in 1995. At one point, they were even engaged, though they soon enough called it off. Paltrow admitted that she wasn’t ready and at the time felt that Pitt was too good for her.
Nicole Kidman and Lenny Kravitz
Before the gorgeous Australian Oscar-winning actress Nicole Kidman married her current husband, Keith Urban, she was once engaged to someone else, and for once, we aren’t talking about Tom Cruise. Rather, Kidman had her sights set on rocker Lenny Kravitz.
Back in 2003, they were happy and all ready to tie the knot, when she decided she just wasn’t ready for the commitment. Fast forward to the future and Kidman is acting in the hit series Big Little Lies alongside Lenny’s own daughter, Zoë Kravitz.
Wilmer Valderrama and Lindsay Lohan
Lindsay Lohan’s personal life has had so many odd plot twists and so many false rumors that it’s hard to get the story straight. And somewhere amidst all that, we missed the fact that she once dated Wilmer Valderrama aka the Fez! They kept it low key, but the truth was out at Lindsay’s 18th birthday.
The relationship did not last and they split up later on in the same year. Not many people knew about this relationship, and both would go on to have their fair share of high-profile relationships with big names in the showbiz industry.
Matt Damon and Winona Ryder
If you have seen The Martian or Good Will Hunting, then you will certainly know Matt Damon. Today, he is famously married to his wife Luciana Barroso, but long before that he was dating a famous actress who was a household name in her own right.
Beetlejuice star Winona Ryder was once the gal of Matt’s life, but the romance came to an end in March of 2000. It’s not all sad though, because Ryder met and married Scott Mackinlay Hahn in 2011. She’s still going strong now with her partner.
Sandra Bullock and Matthew McConaughey
Matthew McConaughey is currently married to the beautiful Camilla Alves, and seeing them together, it’s difficult to imagine him dating anyone else. But long before he met his current wife, he used to date Miss Congeniality herself, the sensational Sandra Bullock.
They starred together in A Time To Kill and started dating. In an interview with Playboy, Matthew McConaughey sang Sandra Bullock’s praises, claiming she could run a country! Even if their relationship didn’t survive, that gigantic compliment will surely live on.
Jessica Biel and Chris Evans
Jessica Biel and current husband Justin Timberlake are considered one of the hottest items in Hollywood, and both halves of this partnership have had more than a few high-profile relationships in the past. For Biel, she had the opportunity to date Captain America.
Well, not exactly Captain America, but the actor who played him, Chris Evans. They started their relationship in 2001, ending five years later in June 2006. It was after this breakup that Biel met Timberlake and the pair got together. Funny how couples move from one person to another in the Hollywood universe.
Scarlett Johansson and Jack Antonoff
Not many remember this pair, and we don’t blame them. Let’s be real: who actually remembers Scarlet Johansson as a sweet little 17-year-old girl, and not someone who plays Black Widow? Many moons ago, teen romance was in the air for Scarlett Johansson and Jack Antonoff.
Their relationship lasted for two years, and they even went to prom together back in 2002. Fast forward to the future and the two are on very different paths in their love lives, with Antonoff’s recent breakup with Lena Dunham, and Johansson’s two divorces.
Lindsay Lohan and Samantha Ronson
Lindsay Lohan once dated English DJ Samantha Ronson. We know, right? We had completely forgotten about this couple as well, but back in the day, they were the talk of the town. The pair came together after Lohan’s relationship with Wilmer Valderrama ended.
Lohan moved onto Hard Rock heir Harry Morton, but their relationship ended all too soon, and before long Lohan was in a relationship with Samantha Ronson. They dated for only a year, and the reason for the relationship’s end, as stated by Lohan, was that: “Two toxic people cannot be together. End of story.”
Josh Hutcherson and Vanessa Hudgens
Troy and Gabriella were on everyone’s mind when High School Musical first came out. So when the stars of the series, Zac Efron and Vanessa Hudgens, started dating, fans everywhere were understandably delighted. Sadly, their relationship didn’t end too well.
However, shortly after that break up, Hudgens dated her co-star on the movie Journey 2: The Mysterious Island, Josh Hutcherson. The relationship did not work out in the end, but Hutcherson says that they became really close friends in the process. It’s nice when couples can become friends after.
Mark Ronson and Rashida Jones
Mark Ronson is famous for producing amazing hit songs that were absolutely inescapable on the radio, like “Uptown Funk” by Bruno Mars and “Back To Black” by Amy Winehouse. And when this once-eligible bachelor of the music world started dating funny girl actress Rashida Jones, everyone loved their chemistry.
While they only dated for a short time, Ronson had actually proposed to Jones in a super cute way! He created a crossword puzzle that ended up with a message that said: “Will You Marry Me?” How cute is that? Unfortunately, the relationship petered out about a year later.
50 Cent and Chelsea Handler
Once upon a time in an Oprah Winfrey interview, comedienne Chelsea Handler declared: “I’m not gonna date somebody whose name is a number.” So why are we mentioning this anecdote? It’s rather ironic considering that she would soon start dating none other than famous rapper 50 Cent.
Apparently, Handler got swept up with the romance and forgot all about her previous statement. Though the two were an iconic duo in the beginning, the relationship did not last. That being said, they remained good friends in the aftermath.
Ryan Gosling and Sandra Bullock
We’re just going out on a limb here to say that this couple would have been super adorable, if they had lasted. Ryan Gosling and Sandra Bullock made a lovely pair on the outside, but their relationship only lasted for about a year before they opted to call it quits.
The fun fact here is that their relationship made the headlines at its time mainly because of their 16-year age gap, with Sandy being the older one. Oh well, at least now we know Sandra has a type: cute and young! Not bad.
Disclaimer: This article was first published on Daveswallet.com and is published here with approval.