Ashton Kutcher & January Jones
Before she made it big on Mad Men, Jones dated then-up-and-coming actor Kutcher from 1998-2001. According to Jones, Kutcher wasn’t exactly boyfriend of the year. “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!”
David Gallagher & Megan Fox
Back when her only film appearance in Mary Kate & Ashley’s Holiday in the Sun, Megan Fox dated 7th Heaven‘s David Gallagher.
Matthew Morrison & Kristen Bell
Bell told Us Weekly in 2010 that she dated the Glee star when they were both students at New York University. “We actually dated very briefly,” she said at the time. “So I’ll have to say maybe Matt Morrison is my favorite part of Glee for various reasons.”
Justin Timberlake & Fergie
The same year *NSYNC released its debut album, Timberlake dated the singer, who had yet to join the Black Eyed Peas. “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.”
Rashida Jones & Tobey Maguire
Years before he become known for starring in the Spiderman movies, Maguire dated Jones, who was just starting out in her career, from 1997-2000.
Ryan Reynolds & Melissa Joan Hart
A relatively unknown Reynolds had a thing for another blonde actress before he wed Scarlett Johansson and then current-wife Blake Lively. After working with Hart, who was rising to fame as the title role in Sabrina the Teenage Witch, he tried to woo the star with a Beluga watch. “He was 17 and I was, like, 19. I was like, “You’re too young for me,” Hart recalled to Chelsea Handler. “I wasn’t sure so I just grabbed him and started kissing him. You get a piece of jewelry like that, you gotta make out with the guy!’”
Lisa Kudrow & Conan O’Brien
Before she took over the small screen as Phoebe on Friends in 1994, Kudrow dated the late night host after they met at an improv class.”He was really smart, really funny, and he thought I was funny,” Kudrow said. After dating briefly, Kudrow noted the pair, “found we were better as friends.”