Gregg DeGuire/WireImage/Getty Images
Jessica Biel & Chris Evans
Long before meeting her now-husband Justin Timberlake, Biel was in a serious, five-year relationship with Captain America. In fact, it was so serious that the two considered marriage. “We always talk about it,” the 7th Heaven actor told Cosmo in 2005. “We both want to be married, and we both want to have children. But we’re not engaged, so the rumors are false … so far.”
Lourdes Leon & Timothée Chalamet
Madonna’s daughter shook the Chalamet hive when she revealed that she used to date the Call Me By You Name actor. “I respect him a lot,” Leon told Vanity Fair in an April 2021 interview. “We were a little item. My first boyfriend.”
Janet Jackson & Matthew McConaughey
During a game of Plead the Fifth on Watch What Happens Live in 2019, McConaughey revealed that he and Jackson went out on a dinner date once and “that was sort of it.” Prior to that, however, he denied all rumors that the two were ever an item.
Dave M. Benett/Getty Images Entertainment/Getty Images
Justin Timberlake & Fergie
When the former *NSYNC was still, well, an active member of *NSYNC, he dated the Black Eyed Peas vocalist very casually. “It wasn’t all that serious,” Fergie told Andy Cohen on a 2017 episode of Watch What Happens Live when she was asked to dish about their past relationship. “Am I allowed to pass on this? Pass. Plead the fifth.”
(Noam Galai/FilmMagic/Getty Images)/(Kevin Mazur/Getty Images Entertainment/Getty Images)
Amy Poehler & John Stamos
“He did a little bit in a movie that I did and a bunch of us hung out. And then later on he’s like, ‘Let’s go get dinner,’” Poehler told Howard Stern of her history with the Full House star. The Parks and Recreation actor also added that the two did not have sex and she was wearing a Leslie Knope shirt on their date — which are obviously two very important details that we can’t leave out.
Sandra Bullock & Ryan Gosling
Bullock and Gosling dated from 2001 to 2003 after meeting on the set of psychological thriller Murder By Numbers. And after some red carpet appearances together where they appeared to be a couple, the Proposal actor told Cosmo in 2003. “Let me see if I can answer that politically and correctly. We’re friends,” she said. However, she also added that if she said they were “just” friends, it would “probably be a bit of a lie.”
Joey Foley/WireImage/Getty Images
Kim Kardashian & Nick Lachey
Long before her marriage to Kanye West (and her marriage to Kris Humphries before that), the SKIMS founder dated Nick Lachey. The two reportedly went on one date, but the Keeping Up With the Kardashians star totally turned him off when she allegedly called the paparazzi in hopes that they would capture their date on camera.
Kevin Winter/Getty Images Entertainment/Getty Images
Lea Michele & Matthew Morrison
When people think about Glee co-stars who’ve dated IRL, Lea Michele and the late Cory Monteith automatically come to mind. But prior to dating Cory and starring on the show, Michele dated another member of the cast: Matthew Morrison. “Matt had been a friend of mine for years, and in fact, we’d actually dated back in the day for a Broadway beat,” the actor wrote in her 2014 book, Brunette Ambition.
Ryan Reynolds & Kristen Johnston
Before Reynolds found his troll-mate in Blake Lively, he had a series of unexpected relationships. Prior to his marriages with Lively and Scarlett Johansson and his engagement to Alanis Morissette, the Deadpool star dated Johnston in the late ’90s. Before that, he also struck up a romance with Melissa Joan Hart on the set of the 1996 TV Movie, Sabrina the Teenage Witch.
(Samir Hussein/WireImage/Getty Images)/(Kevin Mazur/Getty Images Entertainment/Getty Images)
Rihanna & Shia LaBeouf
In 2007, rumors surfaced that LaBeouf and the pop star were an item. However, two years later, the Pieces of a Woman actor squashed all speculation by confirming that they did, in fact, go out on one date. “It never got beyond one date,” LaBeouf told Playboy, according to MTV News. “The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.”