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After Two Years Of Dating, Jon Hamm Is Engaged To Co-Star Anna Osceola

Jon Hamm

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According to a recent story, Jon Hamm is set to tie the knot with his lovely girlfriend, Anna Osceola! Supposedly, 51-year-old Jon Hamm and 34-year-old Anna Osceola are ready to take the leap! People confirmed the story in a piece published on Monday, February 27.

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HollywoodLife has reached out to Jon’s agents for comment, but no response has yet been received. Jon and his leading woman have been dating for some years, but they did not make their red carpet debut until March 2022 at the Academy Awards.

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Prior to that, though, they displayed signs of a serious relationship, as they were spotted kissing on a romantic trip to Italy in September 2021.

Anna first met Jon in 2015, when she participated in the finale of Jon’s career-defining television series Mad Men. And in a 2022 interview, the Top Gun: Maverick actor claimed to be seriously interested in her.

In September, he stated on an edition of The Howard Stern Show, “I’m in a relationship and it’s comfortable, it’s a feeling of taking care of someone and being taken care of.”

Although admitting prior traumas, such as his mother’s death, he stated that he was “moving” toward family life. “I’ve been working on myself, my mental health, and everything else with my therapist,” he told Howard Stern.

“And unraveling all of that pain and realizing that when you lose someone so dear to you, such as a mother, so young, it creates a wound that limits a great deal of emotional accessibility. This substantially reduces that accessibility and vulnerability.”

Yet, he says he is overcoming it. “It’s only been in the last couple of years that I’ve really sat down and thought about all that stuff, which has made the relationship I’m in now even more significant and opened up the possibility of things like getting married, having children, defining a new version of happiness, life, and wellness… “That sounds corny, but it’s real, and — for want of a better term — it’s what I’m working for,” he said.

When the shock jock commented that Jon sounded “in love,” Jon responded, “I most certainly am.”

From 1997 through 2015, Jon was in a nearly two-decade relationship with Jennifer Westfeldt. Anna, a native of Massachusetts, has additionally appeared on Greece, Law & Order: True Crime, and NCIS.

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