At times, it can feel like the Hollywood dating pool is tiny and that everyone has dated everyone. And maybe, perhaps, they have? Long before these celebrities made us laugh and cry with their acting or music, there was a time we didn't know, like, everything about them. We discovered a smattering of celebrity relationships from before the parties achieved mega-fame, from Melissa Joan Hart, who cozied it up with Ryan Reynolds back when they were teenagers, to Keira Knightley and Mr. Grey (um sorry, Jamie Dornan), when he was just known as a Calvin Klein model back in 2003. Also, we couldn't forget to mention Ryan Gosling and his cute baby face as he supported then-boo Sandra Bullock on the red carpet. It almost makes you wonder: Could this have been me? It's like the classic game of "What If?" and Hollywood couples are the category of choice. Here, 48 stars you never knew dated each other when they were just regular people. It's sweet...but mainly shocking.
After starring in an episode of CBS Schoolbreak Special together, 14-year-old Barrymore and 18-year-old Feldman briefly dated. This wasn't the first time this couple got together, though. In Feldman's memoir Coreyography, he wrote the two went on a first date in 1985 when Barrymore was ten, and he was 14. They were set up by his manager at the time—who also happened to be Barrymore's mom.
In the end, he said the two broke up in 1989, due to his heavy drug use while she was trying to get sober.
Before she went on to have the lead in Alias, Garner played Foley's girlfriend on Felicity for two-episodes in 1998 and ended up falling in love with her co-star.
The couple got married in 2000 but split up in 2003. As for why they broke up? Garner believes her and Foley "were the victims of Hollywood."
"Everything is speeded up here — it is a fast-lane life, and if something is not working, it is considered best to end it without much thought," she said, according to InStyle. "If we lived where I was brought up [West Virginia], we would probably still be together."
Before Stan made his way into the Marvel Universe with Captain America: The First Avenger, the couple dated for two years. It's another on-set romance we totally missed, or perhaps don't remember. Either way, the two started dating in 2008 when Meester, who was killing it as Blair on Gossip Girl, met Stan, who played her on-screen fling, Carter.
Meester hinted about the breakup to Seventeen, saying, "I've only had one experience where it was really hard, and I was really sad when it ended, but that's what taught me a lot about myself and love and life – and that's good."
Before Robert Downey Jr. suited up as Iron Man and Sarah Jessica Parker walked the streets of Manhattan as Carrie Bradshaw, these lovebirds dated for eight years. The pair met on the set of the 1984 drama Firstborn when they were 18-years-old. They shortly moved in together in a house in Los Angeles just two months after dating.
They broke things off due to Downey Jr's battles with addiction. "She provided me a home and understanding. She tried to help me. She was so miffed when I didn't get my act together; he told Parade. "I was in love with Sarah Jessica . . . and love clearly was not enough."
After being introduced by a friend and playing BFFs on the set of the 1997 film, Trojan War, the two 18-year-olds hit it off. Hewitt would go on to guest-star as a love interest for Friedle's character Eric in Boy Meets World before Love Hewitt became known for her role in I Know What You Did Last Summer.
Before Jennifer Grey would become a household name for her role in Dirty Dancing, she fell in love with co-star Matthew Broderick on the set of Ferris Bueller's Day Off. Until the summer of 1987, the couple's relationship was a well-kept secret until they got in a head-on crash off the coast of Ireland that ended up killing two people.
The pair broke up afterwards. Grey admitted to People she was never the same after the incident: "The impact was emotional and physical," she said. "My body was never the same. My head was never the same. My ambition was never the same."
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."
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.
Morrison 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 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.
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."
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.
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.
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.
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.
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."
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!"
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!