Most people became fans of Hollywood hunk Jon Hamm after watching his Emmy-winning portrayal of marketing genius Don Draper on AMC's "Mad Men." The critically-acclaimed series shot Hamm, 52, to fame — and led to the actor meeting his wife, fellow actress Anna Osceola.
Since "Mad Men" wrapped its seven-season run in 2015, Hamm followed up his success on the series with roles in films like "Baby Driver," "Richard Jewell," "Confess, Fletch" and "Top Gun: Maverick."
Even with his newfound movie star status, Hamm hasn't completely abandoned the small screen. He joined the cast of "The Morning Show" in 2023 and leads FX's "Fargo" Season 5. Hamm plays a bible-thumping North Dakota sheriff in the critically-acclaimed latest season, and he's been nominated for a Golden Globe for his hilarious—and frightening—portrayal.
While Don Draper's womanizing persona surrounds Hamm, the actor is actually a serial monogamist. He dated actress Jennifer Westfeldt for nearly two decades until calling it quits in 2015. That same year, he found love with actress Anna Osceola, 35. The couple tied the knot in 2023, which Hamm called a "signpost and a signifier of the next chapter" of his life.
Here's everything we know about Jon Hamm and Anna Osceola's love story, from their storybook beginnings on the set of "Mad Men" to their new life as husband and wife.
They Met on the Set of 'Mad Men'
For Hamm, one door was closing just as another was opening. He met Osceola while filming the series finale of "Mad Men" in 2015. She played Clementine, a receptionist at a retreat that Hamm's Don Draper visits in the last episode of the series.
At the time, Hamm was dating Jennifer Westfeldt, whom he'd been with since 1997. And he's been open about the difficulties he faced in his personal life towards the end of "Mad Men." In 2015, Hamm spent a month in treatment for alcohol addiction at a rehab facility. A few months later, he and Westfeldt parted ways.
Hamm seemed to mourn that relationship for a while, telling InStyle two years later: "It's hard to be single after being together for a long time."
In 2017, Hamm was spotted by Extra leaving a coffee shop with Osceola. The next year, the pair were seen by the Daily Mail playing tennis together. Finally, in 2020, the pair confirmed to Us Weekly that they were a couple.
Neither of the actors have social media accounts. But they were spotted vacationing together on a beach in Santa Barbara in 2020 and in the sparkling blue waters along the Italian coast in 2021.
They Took Their Romance Public in 2022
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Nearly two years after making their romance official, Hamm and Osceola made their red carpet debut together at the 2022 Vanity Fair Oscar Party.
Later that year, the couple shared the screen once again in the comedy "Confess, Fletch." Hamm also opened up about his relationship with Osceola in a rare interview on "The Howard Stern Show" in September 2022:
"I'm in a relationship right now and it's comfortable," Hamm said. "It's a feeling of taking care of someone else and being taken care of. And it's also been a process of working on myself, my mental health and all this stuff with my therapist."
The actor said he had been working to unpack the trauma around losing his mother at a young age in order to become emotionally accessible and vulnerable in his relationship.
"It's only been in the last couple of years of me kind of sitting down and really thinking about all that stuff that's made the relationship that I'm in now even more meaningful," Hamm said. "[It has] opened up the possibility of being married, having kids, defining a new version of happiness, life, wellness, all that stuff. It sounds hokey and whatever, but it's real."
Something Wonderful
People confirmed their engagement in February 2023, though a source told the magazine the engagement happened "a while back."
"They are still on cloud nine," the source said. "They have so much fun together and already feel married."
The public finally got a glimpse of Osceola's massive engagement ring at the 2023 Vanity Fair Oscar Party — a simple (but huge!) emerald-cut solitaire diamond.
After confirming he was a soon-to-be married man, Hamm told "Club Random with Bill Maher," "It has changed my life. I'm very happy, it's a wonderful thing."
Even though the actor told Maher he wasn't scared to tie the knot, that wasn't always the case.
More than a decade ago, Hamm told Parade he never intended to get married. And two years later, "The Morning Show" star told Playboy that he didn't believe in marriage.
"My parents got divorced when I was two and never remarried," Hamm explained. "So, it doesn't mean anything to me."
Little did he know that it would just take the right person to sweep him off his feet.
Their Star-Studded 2023 Wedding
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The couple exchanged vows in June 2023 during an outdoor ceremony at the very place they first met. The pair returned to Anderson Canyon in Big Sur, California, where they filmed the final scenes of "Mad Men" together. TMZ reported they even enjoyed "Mad Men"-themed cocktails during the reception.
Hamm and Osceola's nuptials were a star-studded affair, with friends like Paul Rudd, Tina Fey, Larry David and Brooke Shields in attendance.
A few weeks after they tied the knot, Hamm told "Table for Two" podcast host Bruce Bozzi that getting married to Osceola was "the exciting part of life." The Hollywood hunk referred to their nuptials as a "signpost and a signifier of the next chapter and phase that comes with a sense of stability and comfort."
He also acknowledged that taking the leap to marriage could be scary, but that he was looking at the next chapter as "something wonderful."
"It's the reason why I really wanted to do it and really leaned into it and [marriage] is the thing that leads to the next thing in life and that's what I hope — and it's the journey and it's exciting," Hamm said.
