In 2010, Jon Hamm told Parade, “I don’t have the marriage chip.” He was dating Jennifer Westfeldt at the time, and they remained together throughout the entirety of Hamm’s “Mad Men” career. But months after the series finale, they called it quits. “It’s hard to be single after being together for a long time. It’s really hard. It sucks,” Hamm told InStyle in 2017. He started dating actor Anna Osceola three years later.
The couple first met in 2015. On “Mad Men,” Osceola played the pigtailed receptionist working at the hippie retreat where Don Draper comes up with the idea for the Coca-Cola “Hilltop” ad, which, incidentally, features a woman with similar pigtails. When Hamm and Osceola tied the knot in June 2023, they chose to return to the location where Draper either started a totally new chapter of his life or found temporary peace and used it to advance his career: Big Sur, California’s Anderson Canyon. Per Page Six, some of the celebs in attendance were Tina Fey, Paul Rudd, and John Slattery.
Ahead of starting a new chapter of his own life, Hamm shared his updated views on marriage. “It’s exciting because it’s all potential, it’s all possibility, and it’s all positive,” he said on the “Table for Two” podcast around this time, adding, “It gives you and your partner a sense of stability and comfort and an identifying capacity that is better, deeper, richer, than ‘it’s my girlfriend’ or ‘my boyfriend’ or what have you.”
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