Imagine breaking things off with your ex, only to find them starring in the next smash-hit blockbuster the following year, or dominating the global music charts. That was the reality for some of today’s most famous faces, who dated each other before either of them had even reached world domination. Whether young love blossomed as tweens, in the case of Sabrina Carpenter and Bradley Steven Perry, or they simply dated right before they reached superstardom, like Lisa Kudrow and Conan O’Brien, you may be surprised to learn how many Hollywood stars had crossed paths and sparked a romance before their careers took off.
If you’re curious which Little Mix star was ghosted by Harry Styles while he was on The X Factor, or which the big-name superhero Jessica Biel dated before his Marvel heyday, we’ve got you covered. We’re unpacking our top picks for the surprising celebrity couples who dated before fame, how long they were together, and whether or not things ended badly…
Sabrina and Bradley dated while they were both Disney Channel stars
Sabrina Carpenter and Bradley Steven Perry
Before she was the biggest name in pop music, Sabrina Carpenter was a Disney Channel child actor who appeared on Girl Meets World – which is how she met her fellow movie star ex-beau, Bradley Steven Perry. The two had adjacent filming studios, where Bradley was working on Mighty Med, and he conjured up the sweetest way to ask her out.
Bradley ended up writing her a message and delivering it in a bottle – a move he’d like to take credit for, but admitted to the Unplanned podcast, “If I’m honest, I’m certain that, that is something that my mum was like, ‘She’ll find that adorable’…so she probably did it and I gave it to her.” The former Disney star went on to gush about Sabrina, calling her “unbelievably talented” – he’s since married his girlfriend Natasha Bure, Candace Cameron Bure’s daughter, while Sabrina is reportedly still single after her break-up with Barry Keoghan.
© PA Images via Getty Images,WireImageHarry ghosted Jade after making it big on The X Factor
Jade Thirlwall and Harry Styles
While you may have thought Perrie Edwards and Zayn Malik were the only One Direction–Little Mix couple, it turns out Jade Thirlwall and Harry Styles reportedly had a brief fling while he was on The X Factor. Both 16-years-old at the time, Jade recounted the hilarious story to Louis Theroux, saying, “The minute they went on live shows, he didn’t message me back and I thought, ‘That’s it now, he’s gone, he’s made it”.
After Little Mix won the show the following year, the Watermelon Sugar singer ended up apologising. “He said, ‘I’m really sorry that I ignored you,” Jade added, laughing when Louis remarked that he ghosted her. The Angel of My Dreams hitmaker is now in a long-term relationship with Rizzle Kicks’ Jordan Stephens, while Harry is dating Zoë Kravitz.
© WireImageFrom L-R: Kylie Jenner, Cody Simpson, Matthew Rettenmund, and Kendall Jenner in 2011
Kylie Jenner and Cody Simpson
Before she was “King Kylie”, or before she even started dating rapper Tyga, the Kardashian-Jenner sister had another famous boyfriend. She briefly dated Australian popstar Cody Simpson, when the pair were both 14-years-old.
The “Pretty Brown Eyes” singer confirmed that Kylie was “his very first girlfriend” during an appearance on Nova FM’s Fitzy and Wippa in 2022, and it doesn’t sound like there’s any hard feelings between the pair. Kylie is now dating actor Timothée Chalamet, while Cody is in a relationship with Olympic swimmer Emma McKeon.
© Getty Images,ImageDirectThe couple looked loved-up during Mercedes-Benz Fashion Week in 2002
Scarlett Johansson and Jack Antonoff
How many people can say Scarlett Johansson was their prom date? Music producer to the stars Jack Antonoff dated the Black Widow star when they both attended the same high school in New York City, and the pair went to prom together in 2002.
While neither have commented on their past relationship, it’s widely thought that Steel Train’s track “Better Love”, Jack’s first band, is about Scarlett, with lyrics like, “Scars are in her name / And she scars me with blame”. Scarlett has since recorded a cover of the band’s track “Bullet”, so it seems any heartbreak is now water under the bridge. Scarlett is married to SNL funnyman Colin Jost, while Jack tied the knot with Margaret Qualley in 2023.
© WireImageJessica and Chris were looking at getting serious
Jessica Biel and Chris Evans
While they’re both mega-stars now, Jessica Biel and Chris Evans dated for five years in 2001 during the early days of their Hollywood careers. Jessica had made a name for herself in TV’s 7th Heaven (1996–2006), while Chris would go on to have his breakout role as the Human Torch in Fantastic Four (2005).
“We both want to be married, and we both want to have children,” Jessica told Cosmopolitan in 2005. “But we’re not engaged, so the rumours are false…so far.” The couple called it quits the following year, but found their happily ever after. Jessica has been married to Justin Timberlake since 2012, while Chris recently welcomed his first child with his wife, Portuguese actress Alba Baptista.
© NBCUniversal via Getty ImagesThe pair were all smiles during Lisa’s appearance in 2009
Lisa Kudrow and Conan O’Brien
Shortly before Friends made her a household name – and before his world-renowned talk show – Lisa Kudrow and Conan O’Brien had a brief relationship that blossomed from years of friendship, with Lisa even attending Conan’s Late Night audition. The pair remained friends after the break-up, and the Romy and Michele actress has appeared multiple times on the late-night host’s show as well as his podcast, Conan O’Brien Needs A Friend.
In one memorable episode, the pair reminisced over how Conan attended Lisa’s wedding to Michel Stern in 1995, and was seated with the Friends cast – talk about a star-studded table! The late-night host has been married to copywriter Liza Powel O’Brien since 2002.
© Ron Galella Collection via Getty ImagesDespite their break-up, the pair have remained civil
Jennifer Garner and Scott Foley
Jennifer Garner and Scott Foley met on the set of Felicity (1998–2002) after she had a guest role as his character Noel Crane’s girlfriend. During their four-year marriage, the 13 Going on 30 star would go on to have her breakout role in the TV series Alias (2001–2006).
The pair don’t keep in touch, but have bumped into each other over the years, with Scott telling Sirius XM’s Andy Cohen Live, “Everybody says, ‘Hi,’ and you’re cordial and you move on”. Scott married Polish actress Marika Domińczyk in 2007, while Jen, who was previously married to Ben Affleck, is dating tech CEO John Miller.
© Disney General Entertainment Content via Getty ImagesJennifer and Will during their episode of Boy Meets World, which aired in 1998
Jennifer Love Hewitt and Will Friedle
After Jennifer Love Hewitt had a guest role as Eric Matthews’ (Will Friedle) love interest on Boy Meets World in 1998, the pair had a brief romance shortly after the actress’ film breakout role in I Know What You Did Last Summer (1997). The pair also had a bizarrely aggressive make-out session during Jennifer’s episode of the sitcom, which Will has since called “uncomfortable” on his rewatch podcast, Pod Meets World.
“It was super intense,” Will told co-hosts Rider Strong and Danielle Fishel. “And I’ve had people even say to me, like, ‘Oh, when I was a kid, I didn’t realise you guys were together. So, it was just like, what the hell is going on?’” He went on to praise his former love as a “great actress” – Will has been married to Susan Martens since 2016, while the Ghost Whisperer star married Brian Hallisay in 2013, after reconnecting on the set of The Client List.