January Jones and Josh Groban

Josh Groban rose to prominence in the 2000s after releasing four multi-platinum albums. The singer’s first passion was acting, but his career path changed after he stood in for Andrea Bocelli alongside Celine Dion. He already earned his degree of fame in the music scene and earned double-platinum under his belt when he started dating January Jones. She was working on the cinematic diamond American Wedding at the time their love blossomed. They were both in their early twenties — he was 22, and she was 25.

The pair did appear on the red carpet regularly, even though their relationship didn’t make the daily tabloids. In June 2006, they declared they were taking a break and that they intended to remain friends. After that, the story vanished from the front pages. The two seem to be in somewhat different circles at the moment; he is still making his music while she continues to pursue her acting career.