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Jon Hamm Is Engaged to Former ‘Mad Men’ Costar Anna Osceola After Nearly 3 Years of Dating

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Jon Hamm and Anna Osceola. Chelsea Lauren/Shutterstock

Madly in love! Jon Hamm is engaged to his former Mad Men costar Anna Osceola, Us Weekly can confirm.

Related: Congrats! See Which Stars Got Engaged in 2023

“The engagement happened a while back, but they are still on cloud nine,” a source tells Us. “They have so much fun together and already feel married.”

The Top Gun: Maverick star, 51, was initially linked to Osceola, 34, in spring 2020 after being spotted together on multiple occasions. Us confirmed their budding romance in June of that year after the twosome were photographed playing tennis together in Los Angeles in May 2020.

Related: Hottest Couples Who Fell in Love on Set

Two years later, the pair made their red carpet debut while attending an Oscars afterparty in March 2022. Four months later, the lovebirds stepped out for the 2022 ESPY Awards where they posed for photos together.

The duo, who previously shared the screen on the final season of Mad Men in 2015, teamed up once again for 2022’s Confess, Fletch. While promoting the movie, Hamm gave fans a rare glimpse at the couple’s relationship.

“It’s comfortable, and it’s a feeling of taking care of someone else and being taken care of,” the Good Omens actor said during a September 2022 appearance on The Howard Stern Show, noting that he could “for sure” see himself marrying the Law & Order True Crime alum.

Hamm confessed that “unpacking” the trauma of his childhood has helped strengthen his relationship with Osceola. The Emmy winner noted at the time that the death of his mother when he was only 10 years old created a “wound” that negatively affected his emotional availability in the past.

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Jon Hamm and Anna Osceola. NINA PROMMER/EPA-EFE/Shutterstock

“[It’s] made the relationship that I’m in now even more meaningful,” Hamm told Howard Stern of his choice to go to therapy and dive into the past trauma. “And opened up the possibility of things like being married, having kids — you know, defining a new version of happiness, life, wellness.”

The former Unbreakable Kimmy Schmidt star added: “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?”

Related: ‘Mad Men’ Cast: Where Are They Now?

Ahead of his romance with Osceola, Hamm was in a long-term relationship with actress Jennifer Westfeldt from 1997 to 2015.

“With great sadness, we have decided to separate, after 18 years of love and shared history,” the exes said in a joint statement in September 2015. “We will continue to be supportive of each other in every way possible moving forward.”

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