Jon Hamm, Age 48 – Single

For a big part of his life, Jon Hamm had been in a relationship with Jennifer Westfeldt. In fact, they had started dating from even before Jon began working in Hollywood. Their story started in 1997 and ended in 2015, however, they never actually got married, despite being together for over a decade.

They might not have had a paper to establish them as official partners, but their bond was beyond that. Jon thought that people get married to have kids, which they never did, but nor had they ruled out. They broke up once his alcohol addiction became a serious issue. Jon is now set to play in 2020’s Top Gun: Maverick.