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Jon Hamm Is ‘Very Much’ in Love With Girlfriend Anna Osceola, Could See Them Having Kids Together

Jon Hamm Is 'Very Much' in Love With Girlfriend Anna Osceola, Could See Them 'Having Kids' Together
Chelsea Lauren/Shutterstock

Ready to settle down? Jon Hamm gushed about his girlfriend, Anna Osceola, in a new interview — and hinted that the couple are discussing marriage.

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“It’s comfortable, and it’s a feeling of taking care of someone else and being taken care of,” the Mad Men alum, 51, said during a Monday, September 19, appearance on The Howard Stern Show, noting that he could “for sure” see himself marrying his Confess, Fletch costar, 34.

The Emmy winner went on to say that “unpacking” the trauma of his childhood has helped him become a better partner. He noted that the death of his mother when he was just 10 years old had created a “wound” that interfered with his emotional availability, but speaking to a therapist has helped him learn how to be more vulnerable.

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“[It’s] made the relationship that I’m in now even more meaningful and opened up the possibility of things like being married, having kids — you know, defining a new version of happiness, life, wellness,” Hamm told Howard Stern. “All that stuff that sounds hokey and whatever, but it’s real and, for want of a better word, it’s what I’m working for. What else is there other than that?”

When the radio host, 68, asked if he’s in love with Osceola, the Missouri native replied, “Very much so.”

The Baby Driver star and the Law & Order True Crime actress were first linked in 2020 after seemingly meeting several years earlier on the set of Mad Men. Osceola appeared as the character Clementine in the AMC drama’s series finale, which aired in May 2015.

The duo have kept their romance relatively private, but in March, they made their red carpet debut at an Oscars viewing party hosted by Mercedes-Benz.

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More recently, the pair starred together in Confess, Fletch, which premiered on Friday, September 16. Hamm plays the title character while Osceola appears in a small role as Larry.

The Black Mirror alum was previously in a long-term relationship with Jennifer Westfeldt, whom he dated for nearly two decades. The pair announced their split in September 2015.

“With great sadness, we have decided to separate, after 18 years of love and shared history,” the duo said in a joint statement at the time. “We will continue to be supportive of each other in every way possible moving forward.”

Shortly after their breakup, an insider told Us Weekly that the twosome didn’t see eye to eye about starting a family. “There’s always been a rift,” the source claimed at the time. “Because he wanted kids and she didn’t.”

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