Jon Hamm
Jon Hamm, who played Don Draper in the Mad Men series, had a difficult time finding a long-term spouse. Despite the fact that the great actor and producer never married, he had a lengthy line of lovers, none of them were thought worthy of him popping the big question.
The most notable relationship of our first bachelor was not a fling. Between 1997 and 2015, Jon dated Jennifer Westfeldt, a well-known actress and playwright. That’s a lot longer than most marriages nowadays! For over two decades, the couple seemed happy together, but their relationship ended when Westfield decided she no longer wanted to be a mother. According to sources, Hamm’s party-boy lifestyle often put Jennifer in the position of being the responsible adult who had to look after him and clean up his mess. Jon, that’s not good.