At times it can feel like the Hollywood dating pool is rather tiny, and everyone has dated everyone. And maybe, perhaps, they have? In addition to the A-list couples we're all familiar with—Kimye, Brangelina, ChoJo (Priyanka Chopra and Nick Jonas, naturally)—we discovered a smattering of celebrity relationships from before the parties achieved mega-fame. Here, 40 stars you never knew dated each other when they were just regular people.
The duo paired up when they were students at New York University, long before Bell became Veronica Mars and Morrison made a name for himself on Broadway and in shows like Glee. Bell revealed in an interview with Us Weekly in 2010: "We actually dated very briefly. So I'll have to say maybe Matt Morrison is my favorite part of Glee for various reasons."
Morrison later dated his future co-star Michele during their time on the Broadway scene, long before FOX's hit musical show Glee was even a thing. Rumors swirled about their relationship once the series aired, but the actors denied it and attributed their onscreen chemistry to their long-time friendship.
However, Michele came clean about the romance in her 2014 autobiography, Brunette Ambition. "When we shot the pilot, I met Cory Monteith, Kevin McHale, Amber Riley, and Chris Colfer for the first time,” Michele wrote in the book. “I had worked on Broadway with Jenna Ushkowitz and Matthew Morrison before. Matt had been a friend of mine for years, and in fact we’d actually dated back in the day for a Broadway beat.”
These two dated on-and-off for 15 years before they got married on September 6, 1997. They met in the early 1980s at New York City's Atlantic Theater Company, and for Huffman, it was love at first sight. They bonded over a love of acting, and then Huffman "went on a campaign. He was certainly worth it," she told The Daily Mail.
One of the late actor's first gigs was in the 1994 science comedy Tammy and the T-Rex. The movie may not have been a hit (and that's putting it nicely), but Walker did hit it off spectacularly with Richards, his co-star in the film. The ridiculously good-looking couple dated shortly after the film was released before going their separate ways.
The early-to-mid 80s brought Michael Keaton to Hollywood, and he began dating a then-unknown aspiring actress named Courteney Cox. She'd done a recurring role on Family Ties, but her iconic time as Monica on Friends was still a few years away when she and Keaton started dating in 1989. They were together for six years before they split in 1995, a year after Friends blew up.
Talk about hair goals! Lawrence and Russell were a hot item in the 90s, hitting the town together prior to Russell's days as the hate-to-love main character of Felicity. The relationship wasn't without its fair share of drama, though; Russell was still involved with her on-again, off-again boyfriend Tony Lucca of The Mickey Mouse Club at the time.
At the time, he was the teen hearthrob from 7th Heaven and she had two film roles to her name, including the 2001 Mary-Kate and Ashley Olsen film Holiday in the Sun. But they were inseparable for the year they dated in 2003.
It seems like the '80s were a time when future A-listers were all hanging out and dating each other, like George Clooney and Kelly Preston before finding lasting love with their respective spouses (Amal Clooney and John Travolta, of course). Their young romance lasted from 1987 to 1989, and they even lived together with Clooney’s beloved pet pig, Max.
These two started dating when they were both 19, before she had her breakout role in Almost Famous and right after he won our hearts in Rushmore. Deschanel has said Schwartzman was her first "real" boyfriend. The pair broke up in 2005.
Does going on one date qualify as "dating?" If so, Savage and Hewitt definitely dated, but Hewitt's unique choice of pet didn't exactly make a great first impression.
"Fred Savage was my first date," she told a group of former child actresses (including Full House's Jodie Sweeten and Beverley Mitchell from 7th Heaven) on Facebook Live. "Because he was Fred Savage, he was able to get us in very young to the Laugh Factory, we went to a comedy show and dropped me off. And I had a pig as a pet at the time, so I never saw him again, because I had a pig as a pet and he was really creeped out. He was very sweet. I had a huge crush on him."
Now, she's the star of the big screen, and he steals the show on the small, but in 1993, these two were just kids trying to make it big in Tinsel Town. Right after his breakout appearances in School Ties and Scent of a Woman, O'Donnell dated Witherspoon. She was 16 and just moved to Los Angeles.
Bassett and Vance met in the masters' program at the Yale School of Drama in the '80s, and were friends for years before they got together romantically. They married in 1997, and welcomed twins in 2006. “He had a beautiful, beautiful girlfriend at the time, who was also in drama school with us,” Bassett remembers. “So maybe about 14 years later, our paths crossed here in Los Angeles. And I was single, he was single. And I had such an appreciation for him over those years—of his consistency, how he treated other people, of what a supporter he is, what a connector of people and ideas he is, how passionate he is.” Bassett shared with People. That's what a love story looks like!
This one's a shocker! The Taken actor and the Oscar-winner dated for five years in the 1980s—after meeting on the set of Excalibur in 1981—when she was still working to breakthrough in film and he was mostly unknown. According to Neeson, he was smitten by his co-star at first sight, and they started dating soon after filming.
"We didn't date—we lived together," Mirren confirmed during an episode of The Graham Norton Show in 2018. "We were a serious item for awhile."
Before she was on Freaks & Geeks and he was on Roswell, Phillips and Hanks both attended Loyola Marymount University. They dated for a long time, long enough to be with each other when they landed their first roles, and are still friends to this day. “He was my college boyfriend!” she said on Live with Kelly. "We met when I was 18 and Colin was 19…. We are very very close friends now—his wife and I are tight, he and my husband hang out. We go on vacation together."
He was a star on Scrubs, but at the time, she was still an up-and-coming-actress, years away from her starring role on Friday Night Lights. The couple wasn't shy about being seen in public together.
In 1997, before NSYNC had even released their first album, Timberlake and Fergie-Ferg dated (she was a member of girl group Wild Orchid). "He was 16 and I was 23," she told Australia's Courier Mail of her "Where is the Love" collaborator. "It was before he got real heavy with Britney." They've both since had high-profile romances, with Timberlake marrying Jessica Biel (another feature on this list!) and Fergie settling down with Josh Duhamel.
Dewan first met Timberlake when she worked as a background dancer for him after he went solo. When she appeared on Bravo's Watch What Happens Live, Dewan spilled the tea on their short-lived romance. "We dated, not that long," Dewan shyly confessed. "We were like friends ...that dated."
In Lifetime's unauthorized Britney Spears biopic Britney Ever After, Dewan and Spears had a dance-off at a club over Timberlake—totally fictional, Dewan swears. "I really wish I could say that happened, because that would be the coolest story in the world, but it never happened."
All the way back in the days of 2003, Knightley was a working actress, known for part in Bend It Like Beckham, but far from the household name we know today. That year, she started dating Dornan, who at the time was a model for Calvin Klein and more than a decade away from starring in Fifty Shades of Grey. They dated for two years and split in 2005, a year before Dornan's first film credit.
Many of Sheen's romantic relationships have been very public, but one love connection slipped under the radar: his teenage love affair with Wright. The actors were romantically involved from 1981 to 1982.
Before she hit it big with Mad Men, Jones dated then up-and-coming actor Kutcher from 1998 to 2001. According to Jones, he wasn't the shining example of a model boyfriend, though: "He was not supportive of my acting," Jones told GQ in 2009. "He was like, 'I don't think you're going to be good at this.' So, f--k you!"
These two dated on-and-off from 2001 to 2005. She was already fairly well-known for 7th Heaven, but he'd only had bit parts on a few mini-series or TV movies when they hooked up. Needless to say, these two have come very far since they dated.
Before starring as Peter Parker in the early 2000s Spider-Man trilogy, Macguire was in a three year relationship with Jones. After their breakup, Jones went on to discuss her changing perspective on relationships with The Guardian. "I'm happy, but the fact that I'm not married and don't have kids—it's taken me a long time to get to a place where I actually am okay with that, where I actually don't feel like I'm some sort of loser."
The actress later found love with Vampire Weekend frontman Eza Koenig, and the couple has one child together.
Yes, there actually was a time that Brad Pitt wasn't Hollywood royalty. In 1989, before he broke out in Thelma and Louise, the then 26-year-old Pitt began dating his 17-year-old Too Young to Die? costar Juliette Lewis. Despite the age difference, the pair dated for four years before splitting up in 1993. "It amazes me that people are still fascinated that we went out for four years. I was a teenager at the time. It’s a lifetime away. I was in my high-school years and it was a wonderful, loving relationship with a fun, smart guy. Then it was over and he went on to become incredibly famous," Lewis told The Daily Mail in 2010.
If it weren't for Conan, Lisa Kudrow might never have graced our screens, and for that, we thank him. The pair met in an improv comedy class and Kudrow was instantly attracted to him. The duo shared a brief romance before deciding they were better as friends. Her first improv class left her embarrassed and shy, but O'Brien encouraged Kudrow to keep going in her pursuits. And look where they both are now!
In a truly adorable story, Mulligan and the Mumford and Sons lead singer were childhood pen pals who reconnected as adults at a party in Nashville in 2011. They married in 2012, and welcomed a daughter in 2015 and a son in 2017.
Though Simpson's most famous relationship played out before all of our eyes courtesy of her reality series Newlyweds: Nick and Jessica (who could forget that iconic "chicken of the sea" moment?), before that, Simpson dated the star of The CW horror fantasy series Supernatural. In an episode of Newlyweds, Simpson told her then-husband Lachey about the heartbreak that her first love caused her, and fans speculated that she was talking about Ackles.
These two linked up in 1997, a full four years before Westfeldt co-wrote and starred in Kissing Jessica Stein, and a full decade before Mad Men would grace the small screen, launching Hamm into stardom. The pair split in 2015 after 18 years together.
Right around the time that Reynolds really hit his stride in Hollywood as Van Wilder in the 2002 comedy National Lampoon's Van Wilder, he started dating Morissette. The Canadian couple got engaged in 2004, but they decided to go their separate ways in 2008.
The breakup was very hard for Morissette, who later admitted that her seventh studio album, Flavors of Entanglement, was inspired by her heartbreak. “Yeah, it’s really about my grief,” the singer said of the album. “I think the most painful, sort of suffering-oriented moments in my life [are] when I’m resisting something… If I just say, ‘It’s true. I’m unbelievably insecure, really broken, devastated,’ then I can move through it, toward the next place. But if I keep resisting it, I’ll stay there forever.”
These two were the very definition of puppy love when they hooked up in the early 90s (she was 15 and he was 14). They remained together when both of their careers exploded, especially in 2013 after "Blurred Lines" came out. Sadly, they announced their split after 21 years together in 2014.
Gosling had only been in a few films before he was cast in the 2002 psychological thriller Murder by Numbers. Bullock, though, was a household name after starring in films like Speed, While You Were Sleeping, and Miss Congeniality. Still, the co-stars connected on-set and went public with their relationship at the film's premiere.
Even after they split, Gosling had nothing but nice things to say about his ex. "I had two of the greatest girlfriend of all time," he said of Bullock and his other ex, Rachel McAdams. "I haven't met anybody who could top them."
Well...maybe he did; Gosling eventually met Eva Mendes, and they now have two daughters together.