Before achieving Hollywood stardom, Anne Hathaway reportedly dated "That '70s Show" star Topher Grace. Their connection allegedly began in 1999 after meeting at a theater production, and they were rumored to be in a relationship until 2001. The romance was never officially confirmed, but given the timeline, it's likely the duo broke things off as Hathaway's career took off (she got her breakthrough role in "The Princess Diaries," which came out in 2001).

Nearly a decade later, Hathaway and Topher Grace reunited on the set of "Valentine's Day," a 2010 film featuring multiple couples navigating February 14. In the movie, the supposed former couple portrayed a young pair, Liz and Jason, whose new relationship faces challenges when Jason finds out about Liz's secret job as a phone sex operator.

During this time, Hathaway was already romantically involved with her now-husband, Adam Shulman, while Topher Grace was dating Australian actor Teresa Palmer. Despite their respective relationships at the time, Hathaway and Grace showcased convincing on-screen chemistry as a couple, perhaps drawing from past experiences. In a promotional interview with ScreenSlam, they were asked about portraying their characters so realistically, to which Grace jokingly responded, "It was pretty easy." He also cryptically added, "We had a lot of comfort with each other," leaving all of our questions unanswered.