Actress Anna Osceola is no longer Jon Hamm’s girlfriend. She’s his wife now.
Osceola first met Hamm on the set of Mad Men in 2015 and reportedly started dating in 2020. The two have deliberately kept their romance under wraps and have appeared only a handful of times on the red carpet.
Hamm also didn’t talk much about them in his interviews. However, he had been open about feeling settled and comfortable with his relationship.
Then, in February 2023, they reached their first relationship milestone: getting engaged. While most take their time during this chapter, Hamm and Osceola went straight ahead to tie the knot. In June 2023, the two said their vows in a ceremony at Anderson Canyon in Big Sur, California.
Many have grown curious about their relationship and who Anna Osceola is – especially because they have a 17-year age gap. So, we’re here to give you a very brief intro to the actress.
The Girlfriend: Who is Anna Osceola?
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Anna Osceola was born on April 8, 1988. She spent most of her early life in her birth in Cambridge, Massachusetts, until she relocated to California to pursue acting.
She caught her debut role as Charlie in the TV movie “Not Another High School Show” in 2007. Following that, she appeared in various police procedurals, including NCIS and two Law & Order spinoffs, Special Victims Unit and True Crime.
She also had a minor role in the final episode of the period drama series Mad Men. And yes, that’s where she first met Jon Hamm. Don Draper, played by the actor, attended Esalen, a spiritual California retreat, where Clementine, portrayed by Osceola, was a receptionist. The finale was filmed at the Anderson Canyon in Big Sur, California.
It wasn’t until 2020 that the two of them were spotted together and were romantically linked. They were photographed stepping out to ear, playing tennis, and even enjoying each other’s company by the beach. They also vacationed in Italy to spend some time relaxing.
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The couple remained off social media, wanting to be lowkey and just live their lives. Hamm had also spoken about his decision to firmly lay out his boundaries regarding his private personal life and the very public entertainment industry.
Sharing with InStyle back in 2017, he said that that point of life was not to put dog ears on oneself and post it online for everyone to see. While it was fun and adorable, to him, it was the visual equivalent of masturbation, and that there was no point to it other than immediate gratification.
Though, of course, as both actors, red carpets were inevitable. Hamm and Osceola made their red carpet debut in March 2022 at an Oscars afterparty. It was definitely a major step in their relationship, considering they never really liked basking in the limelight. Since then, the two have been occasionally seen on red carpets and in afterparties.
Later that year, fans saw them share the screen in “Confess, Fletch.” It was the film’s third installment, and Hamm took on the role of semi-retired journalist Irwin M. Fletcher, previously portrayed by Chevy Chase in 1985 and 1989. Osceola, on the other hand, played Larry.
Now, A Wife
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Hamm and Osceola’s engagement hit the headlines early in 2023 and was confirmed by PEOPLE in February. A month later, Osceola attended Vanity Fair’s Oscar afterparty wearing her emerald-cut solitaire diamond engagement ring. Then, in June, the two attended the Tribeca Film Festival in New York City for the world premiere of Hamm’s “Maggie Moore.”
The couple didn’t take the long engagement route. On June 24, 2023, they said their vows and “I Do’s” at the Anderson Canyon in Big Sur, California, where they filmed Mad Men’s finale and where they first met! The two kept it classic with their outfits: Osceola wore a simple strapless A-line gown while her groom wore a black tuxedo.
They were definitely excited to enter the new chapter of their lives. In iHeart Radio’s Table for Two podcast, recorded just before the wedding, the actor shared that marriage (ideally) should give both partners stability and comfort. He continued that an identifier of that is a relationship that goes beyond the boyfriend-girlfriend status.
After the wedding, the two flew to the Spanish island of Mallorca for their honeymoon. While the two didn’t share any photos, they were photographed enjoying and soaking under the sun. Osceola sported a yellow bikini, and Hamm wore a pair of mint-green swim shorts.
So, yes, that’s the whole story of how Anna Osceola turned from girlfriend to Jon Hamm’s wife!
