Why Jon Hamm Broke His Rule About Marriage For Anna Osceola
If eternally single George Clooney could get married, then it was only a matter of time before other famous perma-bachelors fell to the siren allure of matrimonial bliss, including Jon Hamm. Tall, handsome as all get-out with a chiseled jaw, and both funny and dramatic in his chosen screen jaunts, it once appeared as if the actor would never tie the knot.
When he rose to the upper tiers of being a well-known face thanks to his career-making role of Don Draper on television's "Mad Men," Hamm was already in the throes of a long-term relationship with fellow actor Jennifer Westfeldt. The two were together for a total of 18 years, but not once did they exchange vows or rings, never getting married. Of their wedding avoidance, Hamm explained to Parade, "I don't have the marriage chip."
That changed with Anna Osceola. The actor met the redhead on the set of "Mad Men;" you can see her as the receptionist at the California retreat Don Draper stumbled into during the last season of the series. When the two came together years later in 2020, it was a quiet start with a big finish — they were married in the summer of 2023 in Big Sur, the same place they originally met. "It's exciting because it's all potential, it's all possibility, and it's all positive," he told "Table for Two" about his decision to become a husband. It seems Hamm had finally located the missing chip.
The actor was ready for the next thing in life
"I always say, 'If it ain't broke, don't fix it."' That was once Jon Hamm's thought process about turning a relationship into a marriage, as he told Amy Raphael. After breaking up with his long-term partner Jennifer Westfeldt in 2015, the actor was still on a career high, moving from "Mad Men" to "Unbreakable Kimmy Schmidt," "Baby Driver," and "Tag," but still struggling with romance.
In 2020, though, cupid struck Hamm in the form of actor Anna Osceola. They were spotted here and there, and made their official red-carpet debut in March 2022. The duo also reunited on screen for the movie "Confess, Fletch." Hamm shared on "The Howard Stern Show" that their relationship was solid, and he was in a comfortable, happy place. "It's a feeling about taking care of someone else and also being taken care of," he described.
After popping the question and planning a wedding, Hamm freely tossed around the word "fiance," and explained to "Table for Two" his reasons for legally committing to his relationship with Osceola. "The reason I really wanted to do it and really leaned into is, this is the thing that leads to the next thing of life. It's the journey. It's exciting. ... And ideally, it gives you and your partner a sense of stability and comfort."
Hamm worked on himself to be ready for marriage
Jon Hamm and Anna Osceola were married in June 2023, and as Hamm recalled on Jimmy Kimmel Live, "It was a perfect day." But before the "Fargo" actor walked down the aisle, he went through a personal metamorphoses that allowed him to form a new opinion about marriage.
Hamm lost his single mother to cancer when he was 10 years old, and shared that it had a big impact on his life, affecting his "emotional accessibility," he told "The Howard Stern Show." He spent time in therapy, working on his mental health. "Its only been in the last couple of years, 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 and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness."
He sees marriage as the next stage in life, the next chapter on his journey, and one he is more than happy to start. The "Top Gun: Maverick" star even has jokes about this commitment, telling Jimmy Kimmel that after they got married overlooking a cliff, they both turned and chose to walk the right way, back through their guests.