Jon Hamm – 50 years old
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We know that Hamm has the look of a total playboy. But he and actress, writer, and director Jennifer Westfeldt were in a committed relationship for nearly 20 years. They just decided never to get married during that time before breaking up in 2015.
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Somehow, Hamm hasn’t found single life to be all it’s cracked up to be despite dating around a little bit. “It’s hard to be single after being together for a long time,” Hamm said in 2017, two years after he and Westfeldt called it quits. “It’s really hard. It sucks.”
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