Celebs Who Dated Before They Hit It Big

We all love a little celeb gossip, especially when it involves who dated who. What surprises a lot of us is how many stars arrived in Hollywood with secret romantic histories. Here are some of the most unexpected pairings from before fame found them.

George Clooney and Kelly Preston’s Early Years

Before Clooney became a household name, he dated fellow up-and-comer Kelly Preston for about two years and they even lived together. Clooney once told People that his relationship with her mattered a great deal. The pair eventually went their separate ways and both later married other people, Clooney to Amal and Preston to John Travolta.

Reese Witherspoon and Chris O’Donnell, Young Lovers

Here are two fresh-faced actors who had a thing before fame took over. Reese and Chris dated back when they were both just starting out, photographed like any cute young couple. Witherspoon went on to roles in Pleasantville and Cruel Intentions where she met Ryan Phillippe, while O’Donnell landed big-screen gigs like Batman & Robin.

Joey Lawrence and Keri Russell’s 90s Connection

Remember Joey Lawrence from Blossom? He was linked to Keri Russell way back in the 90s, back when neither were the mega-stars they later became. Russell went on to headline Felicity and The Americans, and both have kept details of that relationship pretty private. It’s one of those nostalgic 90s stories that makes you do a double take.

Liam Neeson and Helen Mirren, A Five-Year Romance

These two British acting powerhouses actually dated after meeting on the 1981 set of Excalibur. They were together for five years and even lived under the same roof. Although they split, both went on to enormous careers and have stayed on friendly terms. It’s a reminder that long careers can begin with unexpected chapters.

Justin Timberlake & Jenna Dewan

It may surprise you to hear that megastars Justin Timberlake and Jenna Dewan once dated. As you can imagine, the media went wild with this revelation, and tried to unearth as many juicy details as possible. However, Dewan revealed in an interview with Andy Cohen that it was a perfectly respectful relationship, and they remained on good terms even to this day. “We were friends. Then we dated,” she said. “It’s not as salacious as everyone thinks.”

Tobey Maguire & Rashida Jones

We bet you didn’t know that the star of the mega-successful Spiderman franchise and Ann from Parks & Recreation were once an item! Tobey Maguire and Rashida Jones dated for several years before they both hit the big time with their iconic roles. Since going their separate ways, Maguire went on to marry jewelry designer Jennifer Meyer, although they sadly confirmed their split in 2020. Meanwhile, Jones settled down with musician Ezra Koenig and they welcomed a child together.

Lisa Kudrow & Conan O’Brien

Two of the funniest people in showbiz, Friends legend Lisa Kudrow and talk show host Conan O’Brien seem like a match made in hilarity heaven. But did you know that they actually dated many years ago? They met at an improv class before either of them had hit the big time. Kudrow revealed that O’Brien encouraged her to be confident in her own comedy, but though they dated for a while, they eventually decided they were better as just friends.

Jessica Simpson & Jensen Ackles

Remember back in the day when Jessica Simpson’s romantic life was in our TV screens day in day out? Her then-husband Nick Lachay and her starred in one of the first reality TV shows, and won our hearts with their dorky relationship. But Lachey wasn’t Simpson’s first superstar boyfriend—it was in fact none other than future Supernatural star Jensen Ackles! Simpson once blasted Ackles on her reality show, saying that he had cheated on her during their teen dalliance.

Ryan Gosling & Sandra Bullock

Wow! We were really surprised to hear that these two stars once had an unlikely romantic dalliance together. Despite the 16-year age gap, Sandra Bullock and Ryan Gosling got together when they were filming the 2002 thriller Murder by Numbers. Though they remained tight-lipped about the relationship at the time, the two have since both admitted that they were once an item—and it seems they have nothing but fondness for each other. How lovely!

Adrien Brody & Elsa Pataky

To be fair, Adrien Brody was already on the up during this celeb romance, but still we were surprised to hear about it. Brody had just won the Oscar for his role in The Pianist, but Pataky was only known among the Spanish-speaking movie scene. This up-and-coming couple were so in love back in 2006, that Brody bought her a castle. However, that wasn’t enough to keep Pataky’s eye from being caught by a certain Chris Hemsworth … who she eventually married.

Katy Perry & Matthew Thiessen

Katy Perry is so famous these days as a bona fide pop princess, so sometimes it’s easy to forget that she started out in the world of Christian music. Not only that, but she also used to date Matthew Thiessen, the lead singer of Christian rock band Relient K. Back in the early 2000s, the two of them were joined at the hip and Perry was often spotted at his concerts. However, they broke it off in 2005.

Ryan Reynolds & Melissa Joan Hart

Melissa Joan Hart had already cemented her name in the teen drama genre as Clarissa in Clarissa Explains It All when Reynolds still hadn’t quite found his groove. Even still, they met on the set of the movie that would launch the long-running television show Sabrina the Teenage Witch. They were very attracted to each other and dated for a bit, but Hart was still involved with another guy, so it didn’t go very far. They would split up, and several years later, Reynolds would make his mark on Hollywood.

Sofia Vergara & Enrique Iglesias

Yummy! Who knew these equally swoonsome stars once had the hots for each other? We certainly didn’t. To be fair, you can’t really say that Enrique Iglesias ever WASN’T famous, as he was the son of Julio Iglesias, a renowned Latin singer. But even so, he hadn’t quite reached the levels of fame he has today, when he was dating fellow future superstar Sophia Vergara. Vergara of course went on to become the star of Modern Family, and the two eventually went their separate ways.

Drew Barrymore & Corey Feldman

We all know that Drew Barrymore had a pretty crazy past as an infamous Hollywood wild child, but she’s since carved out an incredibly successful career as an adult actor. But back in her wackier days, she had an intense dalliance with fellow young star Corey Feldman. Apparently, it was around the time that Barrymore began to clean up her act and mature a lot, and Feldman wasn’t quite ready for that. They eventually split up, and went on to become even more famous.

Sarah Jessica Parker & Robert Downey Jr.

These two stars have long reigned over our hearts but did you know that they were once deeply in love with each other? Sarah Jessica Parker and Robert Downey Jr. met in 1984, when they were both in the drama Firstborn. They dated for eight years, before Downey Jr.’s personal struggles pushed them apart. Parker went on to star in the iconic Sex and the City, while Downey Jr. had a few more difficult years before striking gold in the Marvel universe as Tony Stark/Iron Man.

Busy Phillips & Colin Hanks

Busy Phillips first burst onto the scene with her roles in Freaks and Geeks and Dawson’s Creek. Colin Hanks was already a bit famous thanks to his dad being Tom Hanks, but he also made a name for himself starring in alien teen epic Roswell. But way back when neither of them were big names, they dated while they were in college together. And they remain friends even to this day, reuniting for a recent TV interview.

Jessica Biel & Chris Evans

Nowadays we know Jessica Beal as a stunning showbiz starlet and of course, the wife of Justin Timberlake, but she actually has another celeb romance in her closet. Because way back before either of them became stars, Biel dated none other than Chris Evans. That’s right—Captain America! They eventually went their separate ways, but the breakup clearly didn’t stand in the way of either of them finding superstardom.

Zooey Deschanel & Jason Schwartzman

We suppose that Zooey Deschanel and Jason Schwartzman have that dorky charm thing going for them, but in this pic, they just don’t seem to have the same star quality they have today. These two cuties dated way back when, before Deschanel had gained fame for her role in New Girl and Schwartzman for The Grand Budapest Hotel and Wine Country.

Fred Savage & Jennifer Love Hewitt

Jennifer Love Hewitt and Fred Savage were the toast of the town back in the 90s, but did you know that they were also buttering each other’s bread?! Well actually, they weren’t quite an item, but they did reveal years later that they had gone on one date together. In fact, this was Jennifer Love Hewitt’s first ever date! They didn’t meet up again though, apparently because Savage was afraid of Hewitt’s pet pig. Did she bring the pig on the date? We have so many questions.

Justin Timberlake & Fergie

It’s hard to remember a time before Justin Timberlake and Fergie were dominating the pop charts, but back in the day they were just regular young people with big dreams. But we bet you didn’t know that the two of them actually dated way back when! Way before NSYNC had released their first record, and before Fergie joined up with the Black Eyed Peas, the super talented pair had a small romantic dalliance. They went their separate ways and of course both ended up becoming superstars.

Charlie Sheen & Robin Wright

You might think you already know all there is to know about Charlie Sheen’s love life, being plastered all over the news as it is. But way back in time, before Sheen was the infamous Hollywood lothario, he dated none other than fellow future actor Robin Wright. Wright of course went on to star in the iconic movie The Princess Bride, while Sheen went on to star in a variety of films before dominating the headlines for his personal antics.

Juliette Lewis & Brad Pitt

We bet you didn’t know that one of the earliest girlfriends of Brad Pitt was none other than Juliette Lewis! The two up-and-coming stars met when they were filming Too Young to Die, and they dated for about four years. After they went their separate ways, Lewis starred in the iconic Natural Born Killers, and Pitt went on to become one of the biggest stars in Hollywood.

Miley Cyrus & Tyler Posey

Before Miley Cyrus got up close and personal with a wrecking ball, she was in a super wholesome and lovey-dovey relationship with the super sweet Tyler Posey. Posey starred in the movie Doc with Cyrus’ dad Billy Ray Cyrus, and the two hit it off straight away. Seeing as they were nine and seven years old, things didn’t get that serious—but omg, so cute!! Cyrus went on to become Hannah Montana before embarking on a super successful pop career, and Posey starred in the smash hit TV show Teen Wolf.

Neil Patrick Harris & Christine Taylor

We all know Neil Patrick Harris for his iconic role as Barney in How I Met Your Mother, in which he engages in some pretty questionable behavior and attitudes towards women. But of course, in real life, he’s happily married to his husband David Burtka. But long before he came out, and even before he got famous, he dated none other than Christine Taylor. Taylor of course went on to marry another funny guy, Ben Stiller.

Jennifer Garner & Scott Foley

We all remember the headlines surrounding Jennifer Garner’s high-profile romance and split with Ben Affleck, but it actually wasn’t her first showbiz marriage. Because way back in the day, Garner starred alongside Scott Foley on the TV show Felicity, and the two fell in love. Not only that, but they tied the knot in 2000—although they divorced only three years later. Garner later opened up to People magazine that she thought it was the pressures of fame that drove them apart.

David Gallagher & Megan Fox

We bet you didn’t know that these two stars once were an item! That’s right—megababe Megan Fox was once super loved up with her fellow actor boyfriend, none other than David Gallagher. The two of them weren’t super famous at the time, but they were on their way to the top. After they split up, Fox of course went on to star in the mega-successful Transformers franchise, and Gallagher carved out a successful career in television.

Matthew Morrison & Kristin Bell

Wow! We had no idea that these two much-loved superstars were once in love with each other. But years later, Kristen Bell revealed to US Magazine that she did indeed once date none other than swoonsome star of Glee, Matthew Morrison! After they had split up, Morrison rose to fame thanks to his part in the hit TV show, and Bell of course went on to star in Veronica Mars, and the iconic Frozen movie franchise.

Scarlett Johansson & Jack Antonoff

Scarlett Johansson is one of the most adored and successful actresses in Hollywood, and Jack Antonoff is a super impressive and famous music producer. But did you know that the two of them dated before they were even famous? Back in their high school days, Johansson and Antonoff were an item for two years! That’s pretty long in high school time. Isn’t it weird that they went their separate ways, but both ended up at the top of their game.

Leighton Meester & Sebastian Stan

OMG! We are delighted to discover that these two were a couple way back in the day. Leighton Meester and Sebastian Stan were an on-screen couple in Gossip Girl? At the time, they were getting pretty cozy off screen as well. After they split up, Stan went on to star in Captain America: The First Avenger, and Meester also carved out a successful career. She also married fellow teen drama icon, Adam Brody.

Jennifer Love Hewitt & Will Friedle

What a cute couple! These two love puppies are none other than Jennifer Love Hewitt & Will Friedle, pictured here before either of them had hit the true heights of their fame. After starring together in the 1997 movie Trojan War, the two of them hit it off and started dating. After going their separate ways, Hewitt went on to become a bona fide A lister, while Friedle became a successful voiceover star. Good for them!

Matthew Morrison & Lea Michele

Wow! We can’t believe Matthew Morrison is on this list twice. But it’s true, he had another romance with another celeb-to-be back in the day! Now, this wasn’t quite before Glee had started, but it was back in the early days before it had really taken off. Years later, the two became super famous, and eventually revealed that they had somewhat of a crush on each other. Did they ever act on it, though? We wonder if we’ll ever find out!

Ashton Kutcher & January Jones

Did you know that Ashton Kutcher and January Jones were once an item? Jones was already a model at the time of their dalliance, but she hadn’t yet quite reached the levels of fame she has now. And as for Kutcher, it would be quite a few years after this that he would make his name on the iconic sitcom That 70s Show. Nowadays, Kutcher is married to his 70s costar Mila Kunis, and Jones keeps the details of her love life pretty private.

Angela Bassett & Courtney B. Vance

These two beauties don’t only each have long and illustrious showbiz careers, but they have an equally long and happy marriage! It was way back in the 80s when the two future stars first met at a prestigious drama school, but it wasn’t until 1994 that they first started dating. Cut to now and the happy couple are still going strong, a true inspiration in career, showbiz, fashion, and couple goals!

Carey Mulligan & Marcus Mumford

This one is truly a story of the ages to warm all hearts. Did you know that Carey Mulligan and Marcus Mumford were sweethearts from long before they were famous? But that’s not all about these super adorable couple that will bring a tear to your eye. Because even before they got together, the two of them were pen pals as children! And when they reconnected as adults, they fell in love and got married! Isn’t that just the sweetest most romantic thing you’ve ever heard?!

Jon Hamm & Jennifer Westfeldt

Here we have another glamorous Hollywood couple whose life together dates way back to before they were famous. We of course know Jon Hamm as the charismatic and unforgettable star of Man Men. But long before he took on that iconic role, he played leading man to none other than Jennifer Westfeldt in his personal life. The two of them were together since 1997, although they sadly went their separate ways in 2015.

Alanis Morissette & Ryan Reynolds

Next up we have Alanis Morrissette and Ryan Reynolds, who were super loved up before either of them reached the true heights of their destined fame. The two Canadian stars were seemingly a match made in heaven, and even got engaged in 2004. Sadly, it wasn’t to be, despite how perfect they seemed for each other—and after a two-year engagement, they broke it off and went their separate ways.

Robin Thicke & Paula Patton

We all know Robin Thicke for his catchy songs with dubious morals and attitude towards women, but what kept him in people’s good books for a while was the fact that he had a long-term and seemingly healthy marriage, with his wife Paula Patton. They first met when they were teenagers way back in 1991, and tied the knot years later before welcoming a son in 2010. However, the hitmaker’s questionable behavior eventually caught up with him, and in 2014 the couple announced their split.

Jay Leno & Sharon Osbourne

Jay Leno is of course known for his iconic role as the host of the long-running talk show The Tonight Show with Jay Leno, but it’s not only his guests and viewers that he has been charming for many years. You may know that he has been married to Mavis Nicholson since 1980, but recently none other than Sharon Osbourne revealed that before they were married, she had had a small fling with the TV star. However it seemed it ended on good terms, as she remains friends with both him and his wife.

Oprah Winfrey & Stedman Graham

Oprah Winfrey is one of the most beloved and powerful women in the world, and as she is such a veritable one-woman powerhouse, many fans might think that she’s single. But in fact, did you know that she has been actually in a long term relationship for over 30 years! Stedman Graham, an educator, author, businessman, and speaker, has been Winfrey’s partner since 1986, and they are clearly deeply in love. Even though they’ve been together so long, they’ve never married—with Winfrey revealing that she felt tying the knot might change their relationship too much.

Michael Keaton & Courtney Cox

Wow! Talk about a celebrity power couple! Michael Keaton and Courtney Cox are two of the most famous and beloved actors in the world, and the idea of them being an item brings us pure delight. However, this glorious pairing actually took place before either of them had reached the true heights of their fame. The two of them dated for about six years, and both of them went on to marry other people—as well as make history in both the TV and movie worlds.

Minka Kelly & Donald Faison

Minka Kelly and Donald Faison are both pretty much household names these days. But did you know that before either of them were famous, they were shacking up together? That’s right! In 2004, Faison was already somewhat known for his role in Scrubs, but his star was destined to only rise greater and greater from this moment. And at the same time, he was dating none other than Minka Kelly, and the two of them stayed together for about a year before going their separate ways.

Keira Knightley & Jamie Dornan

Before Keira Knightley set off on the high seas in her blockbuster adventure franchise Pirates of the Caribbean, and before Jamie Dornan was the romantic lead of a morally dubious power dynamic, the two of them were very much in love behind the scenes. Knightley had just scored her first big role in Bend It Like Beckham, and Dornan was slowly finding success as an underwear model. They dated from 2003 to 2005, and both went on to bigger and better things after parting ways.

Jennifer Grey & Matthew Broderick

We had no idea that these two were once an item! Isn’t that kind of odd, seeing as they played brother and sister on-screen? We guess so, but also they were just teenagers spending a lot of time together while filming Ferris Bueller’s Day Off. And in fact, it was more than a thing—they even got engaged! But eventually they called it off. Grey went on to star in Dirty Dancing and Broderick did a few roles but mostly became known for his marriage to Sarah Jessica Parker.

Nick Jonas & Miley Cyrus

This one seems like a perfect pairing—at the time, at least. Because what more wholesome coupling could there be than Camp Rock star Nick Jonas and Hannah Montana star Miley Cyrus? Though they were still both on their way at the time of dating, it was only after going their separate ways that they both truly ascended to mega levels of fame. Jonas went on to marry Priyanka Chopra, and Cyrus tied the knot with Liam Hemsworth, before splitting up in 2020.

Cameron Diaz & Matt Dillon

These two make a pretty darn attractive couple, but we had no idea that Cameron Diaz and Matt Dillon were once an item! Way back in 1995, the two up-and-coming stars dated for a few years and tried their hardest to keep the romance under wraps. Years later, Dillon opened up to Parade magazine about how wonderful their relationship had been, calling her his muse and saying how he’d never felt that level of love before meeting her.

Johnny Depp & Winona Ryder

Is there a pairing that could more perfectly encapsulate the 90s alternative cool couple, than Johnny Depp and Winona Ryder? These two young starlets were just emerging in Hollywood when they paired up and became one of the most iconic, and just incredibly good-looking, couples in showbiz. Depp famously got a tattoo saying “Winona Ryder”, which after their breakup, he changed to the dubious choice “Wino Forever”. Ok then.

Brad Pitt & Gwyneth Paltrow

Ahh, Pitt ‘n Paltrow! If Winona Ryder and Johnny Depp were the epitome of alternative cool, these two blonde bombshells were the shiny showbiz equivalent. After starring together in the hit movie Seven, the two up-and-coming stars hooked up and started dating just before they both truly hit the big time. Paltrow of course went on to marry Coldplay frontman Chris Martin, and Pitt had not one, but two high-profile showbiz marriages—to Jennifer Aniston and Angelina Jolie.

Demi Lovato & Joe Jonas

Another day, another wholesome Disney pairing from the annals of showbiz past. This time it’s none other than Demi Lovato and Joe Jonas, who both shared a deep and meaningful romantic history before branching out and hitting the big time in mainstream pop. Joe Jonas of course went on to marry Game of Thrones star Sophie Turner, and Demi Lovato has had a string of high-profile relationships, such as with That 70s Show star Wilmer Valderrama.

Jennifer Esposito & Bradley Cooper

Before hitting the big time with hits such as Silver Linings Playbook and A Star is Born, Bradley Cooper was slowly working his way up in the industry and making a name for himself as a talented and versatile actor. And way back when he was just starting his career, he also started up a romantic relationship with none other than NCIS star Jennifer Esposito. The two of them actually even got married! But it didn’t last.

William H. Macy & Felicity Huffman

Though Felicity Huffman and William H. Macy are one of Hollywood’s most famous couples, the truth is that their long and happy marriage far predates their fame. Because they actually met way back in the 80s, at the Atlantic Theater Company. They started dating, but it wasn’t until 15 years later that Huffman finally accepted Macy’s proposal and they got married. Now that’s what we call a very long courtship!

Matthew Morrison: More Than One Crush

Here’s a little follow up on Matthew Morrison’s pre-Glee love life. Years later, Lea Michele confirmed in her memoir Brunette Ambition that she and Morrison had a brief romantic moment back when they were both working on Broadway. Kristen Bell has also spoken about being an old college flame of his, saying they dated very briefly. Looks like Morrison had a few early connections that popped up again once everyone hit the big time.

Katy Perry’s Christian-Pop Era, Revisited

This one fleshes out Katy Perry’s early days a bit more. She didn’t just date Matt Thiessen of Relient K, she was a regular at his shows and even tried to stage dive at one, according to resurfaced footage. The two also collaborated creatively, with material from those days later finding its way into other artists’ recordings. It’s a neat reminder that today’s pop giants often have humble, music-first beginnings.

Colin Hanks and Busy Philipps: College Buddies

We dug up a few more details about Colin Hanks and Busy Philipps. The two actually dated while they were classmates in college, and despite splitting up they stayed close for years after. They’ve talked about how their spouses became friends too, and how the old pals still reunite occasionally. It’s one of those rare Hollywood stories that aged into a genuine friendship.

A Closer Look at SJP and Robert Downey Jr.

A reminder about Sarah Jessica Parker and Robert Downey Jr. They met on Firstborn in 1984 and actually moved in together very quickly, which SJP has referenced when talking about that chapter of her life. Their long relationship eventually ended as Downey Jr. struggled with addiction, and she has acknowledged how hard those years were. It’s a bittersweet footnote to both of their early careers.

Chris Evans and Jessica Biel: On and Off Screen

We also have a few backstage details on Chris Evans and Jessica Biel. The pair dated for several years and even worked together on films like Cellular and London, which gave them time to get close. Biel has recalled sweet gestures from Evans, like waking up to rose petals on her bed for a birthday. It’s another example of two future stars finding each other before either became household names.