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, 22 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 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."
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.
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 exploded on the scene.
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.
Now, she's the star of the big screen, and he steals the show on the small, but in 1993, these two were just two 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 just 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.
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.
All the way back in the days of 2003, Knightley was a working actress, known for roles in Star Wars: Episode 1 - The Phantom Menace and Bend It Like Beckham, but far from the household name we know her as 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.
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.
Yes, there actually was a time that Brad Pitt wasn't Hollywood royalty, and it was within recent memory! 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 paired 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 Mumford 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.
These two linked up in 1997, a full four years before Westfeldt co-write 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.
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.
He's now a hit music producer and she's an ultra-famous actress, but these two dated for two years while attending the Professional Children’s School in New York City. They were even each other's prom dates! But it didn't end smoothly: “When we were in high school, Jack was absolutely obsessed with her, and she broke his heart,” a school pal told Page Six. “They broke up shortly after graduation...She got swept up in the Hollywood scene.”
Hey, we all need some time to figure things out! In 1997, Harris (mostly known for Doogie Howser, M.D.) and Taylor (who'd just appeared in A Very Brady Movie) dated for a brief period of time. "She's the coolest, nicest chick ever. She's an absolute catch. And I thought, If I'm not going to feel the super sparks with her, it probably means I'm gay." Harris later told Howard Stern.