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Jon Hamm and Wife Anna Osceola Are ‘Thinking of Having Kids Soon’ After Wedding (Exclusive)

Jon Hamm and Anna Osceola tied the knot just a few days ago, but an insider says the duo are already considering their next relationship milestone.

Jon Hamm and Anna Osceola's Relationship Timeline

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“He and Anna are thinking of having kids soon,” the source exclusively reveals in the new issue of Us Weekly. “Jon feels like this is the beginning. He’s happy and healthy, and his friends love seeing him like this.”

The Mad Men alum, 52, and Osceola, 35, wed on Saturday, June 24, at an outdoor ceremony held at Anderson Canyon in Big Sur, California. The location played a big role in the series finale of Mad Men, which followed Don Draper (Hamm) as he stayed at the retreat. Osceola played the receptionist at the venue, where Don came up with the idea for the iconic “I’d Like to Buy the World a Coke” ad.

Jon Hamm and Wife Anna Osceola Are Thinking of Having Kids Soon After Wedding-214
Adela Loconte/Shutterstock

“The reception was a blast and the dance floor was energetic at all times,” a second insider tells Us of the couple’s nuptials, which had a star-studded guest list. Hamm’s Mad Men costar John Slattery was on hand for the event along with Tina Fey, Paul Rudd, Larry David, Billy Crudup and Brooke Shields.

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While Hamm and Osceola were briefly linked in 2017, Us confirmed their romance in 2020. The twosome made their red carpet debut at an Oscars party in March 2022. Later that year, they reunited onscreen in the movie Confess, Fletch.

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Jon Hamm and Anna Osceola. Matt Baron/BEI/Shutterstock

In September 2022, Hamm hinted that the romance was getting serious during an interview with Howard Stern. “It’s comfortable, and it’s a feeling of taking care of someone else and being taken care of,” Hamm said at the time, adding that he could “for sure” see himself marrying Osceola.

When Stern, 69, asked whether Hamm is in love with Osceola, the actor replied, “Very much so.”

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In February, an insider confirmed to Us that the duo got engaged a “while back,” adding, “They have so much fun together and already feel married.”

Prior to his relationship with Osceola, Hamm dated Jennifer Westfeldt for 18 years. The former couple called it quits in September 2015. A source told Us at the time that the pair “definitely tried” to stay together, but there was “always a rift” between them. “He wanted kids and she didn’t,” the insider shared.

For more on Hamm and Osceola’s newlywed bliss, watch the video above and pick up the new issue of Us Weekly, on stands now.

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