30 Hollywood Celebrities You’d Be Surprised to Know Have Dated Each Other in the Past

You know how Hollywood seems like a pretty small world sometimes? Well, get ready to be surprised, because the entertainment industry’s dating scene is even more interconnected than you might think. While we all remember the headline-grabbing couples like Brangelina or Tom and Nicole, there’s a whole treasure trove of fascinating relationships that time has almost forgotten.

What makes these forgotten couples so fascinating isn’t just the “wait, they dated?” factor – it’s how these relationships often challenge everything we think we know about celebrity pairings.

Ready to dive into some of Hollywood’s most surprising romantic connections? Let’s start with a couple that might really throw you for a loop.

1 Sandra Bullock and Ryan Gosling

Here’s one that might make you do a double-take: back in 2002, Sandra Bullock and Ryan Gosling were actually an item. Picture this: Bullock was already America’s sweetheart, charming everyone in movies like Speed and While You Were Sleeping, while Gosling was still mostly known as that guy from The Mickey Mouse Club trying to break into more serious roles.

They met on the sets of Murder by Numbers in 2002 and dated till 2003. Short and sweet, as is called. When asked about her equation with Gosling in an interview with Cosmopolitan, Bullock says

Let me see if I can answer that politically and correctly. We’re friends. If you were to add the word just, it would probably be a bit of a lie. So I’d say were friends. [laughs]

Adding on to that, Bullock’s answer to when asked what she learned from Gosling was

To chill. I live my life at a manic pace, and he’s taught me to disregard all that isn’t important. He’s like a little Buddha.

Also think about the timing of this relationship – it happened just before Gosling would steal everyone’s hearts in The Notebook, while Bullock was in the midst of proving she could do way more than just romantic comedies. It’s one of those “right place, right time” stories that Hollywood seems to specialize in.

Despite the 16-year age gap (Bullock was 37 and Gosling was just 21 at the time), the couple had it relatively good. But as it is in Hollywood, their busy schedules got in the way, and they had to break up.

2 Michael Keaton and Courteney Cox

You might want to sit down for this one – Batman and Monica Geller dated once upon a time! When Michael Keaton and Courteney Cox started dating in 1989, they were at fascinatingly different points in their careers. Keaton had just donned the cape and cowl in Tim Burton‘s Batman, while Cox was still working her way up through various TV roles, years before she’d become part of the Friends phenomenon.

What really makes their story interesting is how they managed to keep their relationship going for over five years, right through some major career milestones for both of them. Think about it – during their time together, Keaton became one of Hollywood’s biggest stars, and Cox landed what would become her signature role as Monica on Friends. Talk about a power couple in the making!

3 Janet Jackson and Matthew McConaughey

Here’s a Hollywood romance that really captures the magic of unexpected connections. When Janet Jackson and Matthew McConaughey‘s paths crossed at the 2002 Grammy Awards, it sparked one of those fascinating moments where two very different entertainment worlds collided.

Jackson was exploring new creative directions in her music, pushing boundaries with her album All For You, which had just won her a Grammy. McConaughey, on the other hand, was starting to show signs of the serious actor he would become, though he was still a few years away from what critics would later dub the “McConaissance.”

They only went on one date but, looking back, their brief romance represents a unique moment in both their careers – Jackson continuing to push artistic boundaries and McConaughey beginning the long journey that would eventually lead to his Oscar-winning performances. It’s a perfect example of how Hollywood relationships often occur at fascinating intersections of different career trajectories and artistic journeys.

4 Sarah Jessica Parker and Robert Downey Jr.

Now here’s a relationship that might blow your mind – before she was Carrie Bradshaw and he was Iron Man, Sarah Jessica Parker and Robert Downey Jr. were actually one of Hollywood’s most endearing young couples. Their seven-year relationship kicked off in 1984 when they met on the set of Firstborn, both barely out of their teens and trying to figure out their place in Hollywood.

Think about this – while Parker was transitioning from her Broadway success in Annie to screen roles, Downey was part of that iconic Brat Pack scene that defined 1980s cinema. Their relationship was tumultuous to say the least. In a recent 2023 interview with The New Yorker, SJP says that the relationship made her

feel like a parent at the age off 22.

Their relationship weathered some pretty intense storms, including Downey’s increasing struggles with substance abuse, while Parker was building her reputation as one of Hollywood’s most disciplined young actresses.

5 Jennifer Aniston and Paul Rudd

Here’s a Hollywood relationship that probably slipped right under your radar – Jennifer Aniston and Paul Rudd were actually an item back in 1998. The timing couldn’t have been more interesting: Aniston was at the peak of Friends mania, while Rudd was carving out his niche in Hollywood after charming everyone in Clueless.

What makes their story particularly fascinating is how their brief romance blossomed into one of Hollywood’s most enduring friendships. They’d go on to work together multiple times, including Rudd’s memorable role as Phoebe’s husband Mike on Friends and their later collaboration in Wanderlust. It’s one of those rare cases where a Hollywood romance actually evolved into something even better – a lasting professional partnership and genuine friendship.

6 Cher and Tom Cruise

Ready for this one? Back in the mid-1980s, Cher and Tom Cruise were actually a thing, and the story is absolutely fascinating. Cruise was just a 23-year-old up-and-coming actor fresh off Risky Business, while Cher was already an entertainment icon. They met at Sean Penn and Madonna‘s wedding for the first time and then later on at casual White House event.

What really makes this relationship intriguing is how different they were at the time. Cruise was still that shy, ambitious young actor trying to figure out Hollywood, while Cher was the definition of confidence and stardom. Years later, Cher would spill some pretty interesting tea about their relationship, famously ranking Cruise in her top five lovers!

7 Julia Roberts and Liam Neeson

Let’s talk about a romance that happened way before Julia Roberts was America’s sweetheart or Liam Neeson was fighting bad guys in Taken. Back in 1987, when Roberts was just 19 and Neeson was 35, they fell for each other on the set of Satisfaction.

According to the Kitty Kelley Files: Julia Roberts (via Irish Star), the couple had even moved in together in Venice, California just weeks after meeting each other. Despite a huge age gap, the couple dated for two years before calling it quits and neither of them have revealed why exactly their relationship ended. Talk about an unexpected but significant chapter in both their lives!

8 Ashton Kutcher and January Jones

Here’s a relationship that feels like it’s from an alternate universe – before January Jones was Betty Draper and Ashton Kutcher was, well, Ashton Kutcher, these two were actually a serious item. Their relationship spanned from 1998 to 2001, right when Kutcher was becoming everyone’s favorite goofball on That ’70s Show and Jones was still trying to break into acting.

The really interesting part? Years later, Jones would reveal that Kutcher wasn’t exactly supportive of her acting ambitions, allegedly telling her she wasn’t cut out for it. Oh, the irony! This was all before Jones would go on to earn multiple award nominations for her role in Mad Men. It’s one of those classic Hollywood stories about proving the doubters wrong, and it adds such a fascinating layer to both their career trajectories.

9 Johnny Depp and Ellen Barkin

Back in 1994, Johnny Depp and Ellen Barkin had a whirlwind romance that totally makes sense when you think about it. This was peak ’90s Depp – right after his heartbreak with Winona Ryder and just before his legendary romance with Kate Moss. Barkin, meanwhile, was Hollywood’s go-to actress for fierce, independent women after her standout roles in films like Sea of Love.

Their relationship was evidently a tumultuous one as Barkin later testified against Depp in the infamous Depp v. Heard trial. might have been brief, but it happened at such an interesting crossroads in both their careers. Depp was transitioning from teen heartthrob to serious actor, while Barkin was cementing her status as one of Hollywood’s most respected actresses.

10 Winona Ryder and Matt Damon

Here’s a slice of late ’90s Hollywood that might surprise you: Winona Ryder and Matt Damon were one of the industry’s most intellectual power couples from 1997 to 2000. Get this – they were actually set up by Gwyneth Paltrow, who was dating Damon’s bestie Ben Affleck at the time. Talk about a very ’90s love connection!

Their relationship coincided with some major moments in both their careers – Damon was riding high on the success of Good Will Hunting (hello, Oscar!), while Ryder was transitioning from her iconic ’90s roles to more mature performances. They were often spotted at events together, including the 2000 Golden Globes.

11 Edward Norton and Salma Hayek

Talk about a power couple you might have forgotten about! Edward Norton and Salma Hayek‘s four-year relationship from 1999 to 2003 was actually one of Hollywood’s most intellectually charged partnerships. This wasn’t your typical Hollywood romance – both were known for being fiercely dedicated to their craft and passionate about social causes.

What really makes their story fascinating is how they collaborated on Frida, with Norton secretly helping to rewrite the script without taking any credit. Picture this: Norton, fresh off his mind-bending performance in Fight Club, working behind the scenes to help Hayek bring her dream project to life. The film would eventually earn Hayek an Oscar nomination, proving that sometimes mixing business with pleasure can actually work out beautifully in Hollywood.

12 Ryan Reynolds and Alanis Morissette

Before Blake Lively and Scarlett Johansson, there was Alanis Morissette in Ryan Reynolds‘ love story. Their romance kicked off in 2002 at Drew Barrymore‘s birthday party (how’s that for a meet-cute?). At the time, Reynolds was still mainly known as that funny guy from Two Guys and a Girl, and Morissette was navigating her evolution from an angsty rock star to a mature artist.

Their five-year relationship, including a two-year engagement, was like watching Canadian entertainment royalty in the making. The really intriguing part? Their breakup would later inspire several tracks on Morissette’s album Flavors of Entanglement. Talk about turning heartbreak into art!

13 Cameron Diaz and Jared Leto

Here’s a relationship that might make you do a double-take: Cameron Diaz and Jared Leto, dated between 1999 to 2003, and were living together. This happened right when Diaz became Hollywood’s highest-paid actress after There’s Something About Mary, while Leto was juggling his acting career with fronting his band 30 Seconds to Mars.

Rumors were floating around that Leto became jealous of Diaz’s growing success and ended the relationship to focus on his band, 30 Seconds to Mars. It was also suggested that the couple lived separate social lives and Leto wasn’t very nice to Diaz. All of this is alleged since neither Leto nor Diaz have ever confirmed the reasons.

14 Christina Applegate and Brad Pitt

Remember that time Christina Applegate took Brad Pitt to the 1989 MTV Movie Awards and then… left him there for someone else? It’s true, and it’s one of Hollywood’s most legendary “what if” stories! This happened when Applegate was already a household name from Married… with Children, while Pitt was still that gorgeous unknown guy waiting for his big break.

The mysterious person was never revealed but Applegate did say that after that incident, there were no more dates with Pitt. The best part is how this story has become such a beloved piece of Hollywood folklore that Applegate still gets asked about it decades later. It’s one of those moments that reminds us that even future megastars can get dumped at award shows!

15 Matthew Morrison and Lea Michele

Before they played teacher and student on Glee, Matthew Morrison and Lea Michele had a brief romance during their Broadway days – talk about life imitating art in reverse! This happened when both were performing in different shows on Broadway, years before they’d come together to create musical theatre magic on television.

It is admirable to see how they managed to keep it professional when they later worked together on Glee. Imagine having to play a teacher-student relationship with someone you used to date! The fact that most fans didn’t even know about their past until years later speaks volumes about their professionalism. It’s one of those Hollywood full-circle moments that proves what a small world the entertainment industry really is.

16 Mila Kunis and Macaulay Culkin

Now here’s a relationship that really shows how Hollywood works in mysterious ways. Mila Kunis and Macaulay Culkin managed to keep their romance going for eight years, from 2002 to 2010, while navigating some pretty intense career transitions. When they started dating, Kunis was just finding her footing on That ’70s Show, while Culkin was trying to figure out life after being the biggest child star in the world.

Additionally, it was also the time when Kunis was becoming a household name, Culkin was deliberately stepping away from the spotlight. They rarely appeared in public together and kept their relationship so low-key that most people didn’t even realize they were a couple until after they broke up.

17 Helen Mirren and Liam Neeson

If you thought Liam Neeson’s action hero persona came out of nowhere, wait until you hear this story. Back in 1980, Neeson and Helen Mirren fell in love on the set of Excalibur, where they were playing Sir Gawain and Morgana Le Fay. Picture this: a relatively unknown Irish actor catching the eye of one of Britain’s most respected theatrical actresses in the midst of filming a medieval fantasy epic.

During an interview at The Graham Norton Show where both of them appeared together, Mirren revealed

We didn’t date, we lived together for four years. We were a serious item for a while. Lucky me!

The really incredible part? Mirren basically kickstarted Neeson’s international career by helping him get his first agent. Their four-year relationship wasn’t just about romance – it was about mentorship, professional development, and two incredibly talented actors supporting each other’s dreams. Talk about a relationship with lasting impact!

18 Jake Gyllenhaal and Kirsten Dunst

Here’s a relationship that perfectly captures early 2000s Hollywood romance. Jake Gyllenhaal and Kirsten Dunst were introduced by Jake’s sister Maggie Gyllenhaal, who had worked with Dunst in Mona Lisa Smile. At the time, both were on the verge of even bigger stardom – Dunst was fresh off the success of Spider-Man, while Gyllenhaal was transitioning from indie darling to mainstream star.

Their relationship coincided with both actors taking on more mature roles and establishing themselves as serious artists. Dunst was balancing blockbuster success with critically acclaimed indie films, while Gyllenhaal was about to enter a career-defining period with films like Brokeback Mountain on the horizon.

They were the definition of a power couple in the making, both professionally and personally. Though their relationship ended in 2004, both actors have spoken respectfully about their time together in subsequent interviews.

19 David Gallagher and Megan Fox

Remember when Megan Fox wasn’t yet MEGAN FOX? Well, back in 2003, she was dating 7th Heaven star David Gallagher. This was just before her transformation into a global sensation with Transformers. At the time, Gallagher was the bigger star, known to millions as Simon Camden on one of TV’s most popular family shows.

What makes their relationship particularly interesting is how it captures that moment right before everything changed. Fox was still doing guest spots on various TV shows, while Gallagher was trying to transition from child actor to adult roles. Within just a few years after their breakup, Fox would become one of the most famous women in the world. Talk about timing!

20 Owen Wilson and Sheryl Crow

Picture this: It’s 1999, Owen Wilson is filming The Minus Man, trying to prove he’s more than just the guy who co-wrote Rushmore, and in walks Sheryl Crow, riding high on her musical success. Their romance blossomed during the filming of this dark indie film, which was quite a departure from Wilson’s usual comedic roles.

They dated for two years, making the rounds at high-profile events like the 2000 Vanity Fair Oscar party. Though the relationship didn’t last, it left a lasting impression on Crow’s music. She later dedicated “Safe and Sound” from her 2002 album C’mon, C’mon to Wilson, turning their shared history into a poignant musical memoir.

21 Gary Oldman and Uma Thurman

Let’s wind back to 1990 when Hollywood witnessed one of its most intriguing unions. Gary Oldman, the intense British actor known for completely disappearing into his roles, married Uma Thurman, who was just 20 years old and on the verge of becoming Hollywood’s next big thing. Think about the timing – Oldman was already earning acclaim for his transformative performances, while Thurman was turning heads with Dangerous Liaisons.

Their two-year marriage coincided with some major career moments for both actors. Thurman was pushing boundaries with Henry & June, the first NC-17 rated film, while Oldman was cementing his reputation as one of Britain’s finest exports to Hollywood. The marriage might have been brief, but it happened during a crucial period when both were defining their artistic identities.

22 Carson Daly and Jennifer Love Hewitt

If you want to understand late ’90s pop culture, this relationship pretty much sums it up. Carson Daly, MTV’s resident cool guy and host of TRL, dating Jennifer Love Hewitt, America’s teen queen from Party of Five and I Know What You Did Last Summer. Their romance became a perfect snapshot of late-’90s celebrity culture.

During their year-long romance in 1997, Daly and Hewitt were regulars on the red carpet circuit, with Daly even getting her name tattooed on his leg – talk about commitment! But the relationship ended as dramatically as any ’90s teen movie, with Daly reportedly learning about their breakup through The Howard Stern Show.

Daly told People magazine in 2000 (via E! News)

I woke up to Howard Stern telling me my relationship with [Jennifer] was over. Then I heard Steve Kmetko on E! say, ‘Just off the Associated Press: Jennifer Love Hewitt and Carson Daly have officially broken up.’ If we were going to break up officially like this, maybe we could have just talked about it. I don’t see why you had to tell your publicist. And now I have been publicly humiliated.

Though things ended messily, they eventually buried the hatchet when Hewitt appeared as a guest on Last Call With Carson Daly in 2005.

23 Lance Armstrong and Ashley Olsen

Talk about an unexpected pairing! When Lance Armstrong and Ashley Olsen started dating in 2007, people couldn’t quite wrap their heads around it. Armstrong was fresh off his split from Sheryl Crow and still a cycling hero (before the controversy), while Olsen was working hard to shed her child star image and establish herself in the fashion world.

The relationship ultimately ended, and Armstrong moved on to Kate Hudson, but it was a fascinating part of their respective careers.

24 Justin Timberlake and Fergie

Here’s a piece of pop music history that might surprise you: back in 1996, a 16-year-old Justin Timberlake briefly dated Fergie, who was 23 at the time. This was when NSYNC was just starting out and Fergie was still performing with Wild Orchid, years before The Black Eyed Peas would make her a global superstar.

The age gap later became a topic of discussion, but at the time, both were just young artists trying to make it in the music industry. It’s fascinating to think about this relationship now, considering how both would go on to become massive stars in their own right, though in very different ways. Talk about a “before they were famous” moment!

25 Zach Braff and Mandy Moore

Here’s a throwback that might surprise you: Before her current happy family life with Taylor Goldsmith, Mandy Moore once dated Scrubs star Zach Braff! The pair got together in 2004 after Moore’s split from tennis star Andy Roddick. While they started quietly, their relationship eventually led to some professional overlap – Moore even guest-starred on Scrubs and later channeled their relationship into songs on her album Wild Hope.

In a 2006 Cosmopolitan interview, Moore gushed about how supportive Braff was of her career, but the romance wasn’t meant to last. After their split, Moore candidly told People (via Hollywood Life),

We weren’t like a big ‘going out’ couple. But when the relationship ended, it was ‘a bummer.’

She added that breakup was the icing on the really bad cake. The burned cake.

Braff later admitted on The Howard Stern Show in 2014 that dating someone famous wasn’t his thing. Moore went on to marry and divorce musician Ryan Adams before finding her happy ending with Goldsmith, with whom she’s now raising two children.

26 Josh Hutcherson and Vanessa Hudgens

Speaking of unexpected couples, did you know Josh Hutcherson and Vanessa Hudgens once had a brief romance? The two had only met in passing before being cast together in Journey 2: The Mysterious Island. Despite their four-year age gap (he was 18, she was 22), they grew close during filming and were spotted getting cozy at various outings – from Coachella to Lakers games, and even a PDA-filled bowling date.

But here’s the kicker: they tried to keep their relationship as much of a secret as possible, that was until they broke up. During a 2012 press appearance on Australia’s Today show, when asked about dating, Hutcherson playfully quipped,

We were at one point, but she broke my heart. No, kidding. That was a while ago. We’re just really good friends now.

Hudgens confirmed their just-friends status with an endearing pat on his cheek – talk about handling an awkward moment gracefully!

27 Nick Cannon and Kim Kardashian

Here’s a pre-KUWTK romance that might shock you: Nick Cannon and Kim Kardashian were once an item! The two first crossed paths when Kim was working as a stylist on Moesha – yes, this was way before reality TV stardom and billion-dollar businesses. After her split from Ray J in 2006, Cannon and Kim dated from late 2006 to early 2007. And it wasn’t just a casual fling either.

Years later, on a 2021 episode of Drink Champs, Cannon opened up about the relationship, admitting

I was really into her, I was vibing… She broke my heart.

But there’s clearly no bad blood between these two media moguls – in 2014, Cannon had nothing but praise for Kim and her family, calling them

some of the most incredible people I’ve ever met.

Talk about a throwback romance that nobody saw coming!

28 Kiefer Sutherland and Julia Roberts

This relationship isn’t just about who dated whom – it’s about one of Hollywood’s most dramatic “almost-weddings” ever. Picture this: It’s 1991, Julia Roberts is already America’s sweetheart after Pretty Woman, and Kiefer Sutherland is one of Hollywood’s most promising young actors. They’re planning this lavish wedding at 20th Century Fox’s Soundstage 14, transformed into a garden paradise.

But here’s where it gets really interesting – just three days before the wedding, Roberts calls it off.

As per the rumor mill, Roberts discovered Sutherland’s involvement with a go-go dancer, though the full truth might never be known. Instead of heading to the altar, Roberts reportedly spent her would-be wedding day hanging out with Sutherland’s friend Jason Patric. Now that’s what you call Hollywood drama!

29 Tyra Banks and Seal

Here’s a ’90s romance that might surprise you: before Seal‘s famous marriage to Heidi Klum, he actually dated another supermodel – Tyra Banks! The pair made a rare public appearance together at the Essence Awards shortly after Banks’ split from John Singleton.

While they kept their relationship largely under wraps (so much so that we don’t even know how long they dated!), their connection made for an interesting twist years later when Banks and Klum would go on to work together, posing for campaigns and walking the Victoria’s Secret runway side by side.

When asked on Watch What Happens Live if his album Human Being was inspired by Banks, Seal kept it cool, saying

It wasn’t inspired by her but we bump into each other every now and then, there’s no drama.

Talk about a small world in the modeling and music industry!

30 Robert De Niro and Naomi Campbell

Let’s wrap up with a relationship that perfectly captures how Hollywood can create the most unexpected connections: Oscar-winning actor Robert De Niro and supermodel Naomi Campbell! While many celebrity relationships play out in the spotlight, these two managed to keep their relationship in the ’90s impressively private. Even thought the details of their romance remained under wraps, the relationship clearly left a lasting impression – especially on Campbell.

Naomi Campbell and Robert De Niro were an item back in the '90s, and while their romance didn't work out, they've maintained a friendship ever since. https://t.co/PwYy84wssg

— The List (@TheListDaily) December 28, 2024

In a revealing interview with WSJ. Magazine (via People), she shared a profound life lesson she learned from De Niro.

Being alone doesn’t mean you are lonely. I was taught that by Robert De Niro.

What’s even more refreshing about this surprising pair is how they’ve maintained their connection over the years. Unlike many Hollywood breakups, these two stayed on genuinely good terms. Campbell confirmed this to The Times, noting that she remains friends with all her exes (except the last one), and even mentioned catching up with De Niro just before the 2020 lockdown.

These unexpected pairings remind us that Hollywood romance is often about being in the right place at the right time, regardless of age, background, or career trajectory. Each relationship tells its own unique story about ambition, timing, and the ever-changing landscape of entertainment industry dynamics.