Jon Hamm is no longer available. According to a PEOPLE article on Feb. 27, the Mad Men actor is engaged to his Confess, Fletch co-star Anna Zimmer after two years of dating. Hamm and Osceola met on the set of Mad Men in 2015, during the last season of the AMC series. After 18 years together, Hamm and Jennifer Westfeldt announced their separation in September 2015.
Continue reading below
Meanwhile, Osceola, a native of Massachusetts, appeared on NCIS and In Plain Sight, gradually building her television profile. Rumors of their relationship first appeared in 2017, but they became more public when the pair was pictured out and about in 2020. Both stars are notoriously secretive and avoid social media, although they’ve made countless red-carpet appearances together throughout their relationship.
From their first encounter to their engagement, here’s all we know about their relationship.
Osceola appeared as a receptionist called Clementine at a retreat checked into by Hamm’s Don Draper in “Person To Person,” one of the series’ last episodes. After dating since 1997, Hamm and Westfeldt also split up that year. In a joint statement, they announced their split, pledging to “continue to be supportive of each other in every manner possible moving ahead.”
Continue reading below
When the stars were pictured together on a beach in Santa Barbara, California, in 2020, they were thought to be dating. “They appeared really happy together,” a source told PEOPLE at the time. They do appear to be dating.” Though they had previously been seen together in 2017, this outing appeared to fuel fresh suspicions of a romance.
Hamm and Osceola made their red carpet debut at the Vanity Fair Oscar Party at the 2022 Academy Awards. According to Page Six, they also attended the Mercedes-Benz Academy Awards afterparty that night.
Hamm and Osceola kept their relationship quiet until September 2022, when Hamm revealed it. “All of this is part of what I’m saying. There is just another location in my life where I feel completely at ease. ” I’m in a relationship right now, and it’s pleasant,” he told Howard Stern during an appearance. He also stated that he was more open to “the potential of things like marriage, having children, and establishing a new definition of happiness, life, and wellbeing.”
Continue reading below
“That sounds cheesy and whatever, but it’s true, and, for want of a better phrase, it’s what I’m striving towards,” Hamm continued. “Is there anything more except that?”
When the film Confess, Fletch aired in 2022, Hamm and Osceola were reunited onscreen. The film, which was shot in 2021, functioned as a sort of Mad Men reunion, with John Slattery (Roger Sterling) also appearing.
On February 27, PEOPLE claimed that Hamm and Osceola were engaged. Hamm and Osceola have yet to officially comment on their engagement.
