MAD LOVE: How Jon Hamm's 'Mad Men' co-star Anna Osceola made him change his views on marriage
LOS ANGELES, CALIFORNIA: The television show 'Mad Men' significantly changed Jon Hamm's life. Not only did it make him a global star, it also helped him meet his fiancee and maybe, future wife. Anna Osceola, 34, first appeared on the AMC show as a receptionist eight years ago. Soon after, Ham, 51, ended his 18-year relationship with Jennifer Westfeldt and went down on one knee for Osceola.
It never crossed anyone's mind that Osceola may have had anything to do with Hamm and Westfeldt's separation. However, when he and Osceola started dating several years later, a question lingered: Did she have something to do with Hamm and Westfeldt's breakup?
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The 'Mad Men' couple
Hamm and Osceola, who is from Cambridge, Massachusetts, first met on 'Mad Men' in 2015. Hamm portrayed Don Draper, while Osceola played Clementine, a receptionist at a resort that his character visited in one of the last season's episodes, per Daily Mail.
Sparks flew almost instantaneously because Hamm and Osceola were crazy for each other. Initially, Hamm maintained that he would never marry, which has changed now that he reportedly said he may marry her. The two are often seen cozying up together. Other than that, not much is known about their relationship.
After they were spotted playing tennis together in May 2020, it became quite clear they were together. They were seen more than once being all lovey-dovey. In September 2020, they went to the Santa Barbara, California, beach together. In September 2021, they took a romantic vacation to Italy. In March 2022, they started appearing together at red-carpet events together. In September 2022, they co-starred in the movie 'Confess, Fletch'.
Not exactly camera shy, the couple did not reveal much about each other. They hardly ever said anything about one another in interviews, and neither is active on social media. In an interview with InStyle, Hamm had said of social media, "The point of life is not to put dog ears on yourself and post it online for everyone to see."
How did Anna Osceola change Jon Hamm?
During an interview with Sirius XM in September 2022, Hamm admitted that he was rethinking his stance on marriage after believing for years that he would never be enthusiastic about getting married. "[I'm in] another place in my life where I feel very settled and comfortable. I'm in a relationship right now and it's comfortable," he remarked.
The actor stated that after years of battling with the trauma he experienced as a child when he lost his mother to colon cancer at the age of 10, he recently started focussing on addressing his mental health struglles and substance abuse difficulties through therapy. He said that seeking professional help "opened up the possibility of things like being married and having kids."
When Hamm and Westfeldt were still dating, he declared that neither of them was interested in getting married. He appeared to be equally uninterested in having children. "I like kids but I also like the option to close the door," he reportedy said. It has all changed now as Us Weekly reported that he and Osceola were engaged. However, sources said he popped the question "a while back."
What happened between Jon Hamm and Jennifer Westfeldt?
Soon after their separation, the former couple issued a joint statemtn which read, "With great sadness, we have decided to separate, after 18 years of love and shared history. We will continue to be supportive of each other in every way possible moving forward."
While Hamm had just completed a 30-day stint in rehab for alcoholism, there were rumors that his "party-heavy lifestyle" was to blame for the breakup. Sourced told ET, "Jon and Jennifer really fought hard to make their relationship work, Jennifer more so than Jon."