Jon Hamm Reportedly Engaged to Longtime GF Anna Osceola

The ‘Mad Men’ alum is said to have proposed to the 34-year-old ‘Bull’ actress, whom he started dating in 2017 following the end of his 18-year relationship with Jennifer Westfeldt.

AceShowbizJon Hamm is reportedly engaged to Anna Osceola. The “Baby Driver” actor, 51, is said to have proposed to the 34-year-old “Bull” actress after they first got to know each other while working on “Mad Men” together in 2015, when Anna landed a role as receptionist Clementine at the retreat Jon’s character Don Draper attended in the final episode of the drama.

The engagement was reported by People on Monday, February 27, but the outlet said Jon’s representative hadn’t yet commented. At the time Jon met Anna, he was in an 18-year long relationship with “Grey’s Anatomy” actress Jennifer Westfeldt, 53, before they broke up in 2015 after repeatedly saying they never wanted to wed.

Jon and Anna have been spotted together since 2017 and talk they were an item grew in 2020 when they were seeing doing errands for each other during the COVID-19 lockdown. The actor, who has said he is intent on keeping his private life off social media, admitted in September 2022 in an interview with Howard Stern show he could see himself one day settling down.

He said, “I’m in a relationship right now and it’s comfortable.” Jon added he had recently been able to start “really thinking about all that stuff,” saying, “That’s made the relationship that I’m in now even more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness.”

He went on, “It sounds hokey and whatever, but it’s real and for one of a better word, it’s what I’m working for. What else is there other than that?” Jon and Anna have been seen on screen together since “Mad Men”, appearing together in 2022’s “Confess, Fletch“, with Jon playing amateur sleuth Irwin M Fletcher, originally played by Chevy Chase.

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