Jon Hamm Engaged To Girlfriend & Co-Star Anna Osceola After 2 Years Of Dating: Report

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Jon Hamm, 51, is reportedly ready to take the plunge with his girlfriend Anna Osceola, 34! People confirmed the news in a Monday, February 27 report. HollywoodLife has reached out to Jon’s representatives for comment but has not yet received a response. Jon and his leading lady have been dating for a couple of years, but they didn’t make their red-carpet debut until the Oscars in March of 2022. They gave out hints of a serious relationship before that, however — they were seen making out during a romantic getaway to Italy in September of 2021.

The duo first met back in 2015, when Anna appeared on the series finale of Jon’s career defining series Mad Men. And in an interview back in 2022, the Top Gun: Maverick actor admitted to being serious about her. “I’m in a relationship right now and … it’s comfortable, it’s a feeling of taking care of someone else and being taken care of,” he said in September on an episode of The Howard Stern Show.

While acknowledging past traumas, like the death of his mother, he also said he was “working” for a family life. “It’s also been a process of working on myself, my mental health, all the stuff with my therapist,” he told Howard Stern. “And unpacking all of that trauma and realizing that when you lose someone that’s so important to you, like a mother, so early, that that creates a wound that blocks a lot of that emotional accessibility. That blocks a lot of that availability and vulnerability.”

Still, he said, he’s working past it. “It’s only been in the last couple of years, me kind of sitting down and really thinking about all that stuff, 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 … It sounds hokey and whatever, but it’s real and it’s — for want of a better word — it’s what I’m working for,” he said. When the shock jock said it sounded like Jon was “in love,” he replied, “I very much so am.”

Jon was previously in a nearly two-decade relationship with Jennifer Westfeldt from 1997 to 2015. Massachusetts native Anna has also appeared on Greek, Law & Order True Crime and NCIS.