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!”