LOS ANGELES, CALIFORNIA: On Saturday, June 24, Jon Hamm tied the knot with fiance Anna Osceola at Anderson Canyon in Big Sur, northern California, nearly eight years after they first met while filming the final season of ‘Mad Men’ at the same location. While Hamm garnered immense global recognition for playing the iconic role of Don Draper in the hit AMC show, Osceola only appeared on a single episode in the last season, playing the role of Clementine, a receptionist who worked at the retreat where Hamm’s character stayed.
When Hamm and Osceola first crossed paths in 2015, the former was already in a longtime relationship with actress Jennifer Westfeldt. While it is not known whether the meeting had an impact on Hamm and Westfeldt’s relationship, the couple called it quits the same year after an 18-year-long relationship. The split left people shocked as Hamm and Westfeldt were one of Hollywood's longest-running couples. Hamm was eventually spotted with Osceola in 2017 and their romance was confirmed in 2020. 2022 was a big year for the couple as they made their red carpet debut and worked together in a film titled 'Confess, Fletch'. While the exact date the couple got engaged is not known, they confirmed their engagement in February 2023.
Jon Hamm and Jennifer Westfeldt's first meet
Hamm and Jennifer Westfeldt’s first met in 1997 when they were both struggling actors, long before the former earned worldwide fame for his work in ‘Mad Men’. “Jen and I met in LA at a party — a mutual friend's birthday party... completely random meeting... she was out here auditioning for a pilot or something... and I was, too... and she got an audition for Jake Kasdan's film ‘Zero Effect [1998]’ and wanted to read with somebody who was a guy, and she didn't really know any guys out here, so she called... and that was, kind of, how we first officially met, running scenes from 'Zero Effect',” Hamm told Hollywood Reporter.
“Apparently I wasn’t very good, 'cause she didn’t get the part,” the actor added. He also recalled that Westfeldt was dating someone else at the time and that the pair did not start dating until later. “She was involved with somebody, and I may have been involved, as well. Yeah, we were friends for a long time before we officially started dating — and we've never gotten out of the ‘dating’ thing. We're still in it,” Hamm shared in a 2011 interview, years before he met Anna.
Meanwhile, Westfeldt told The Guardian that she initially thought Hamm was “arrogant” after a friend recommended her to read lines with him. “You mean that arrogant guy from the party? No thank you,” the actress recalled thinking. However, Westfeldt’s opinion of Hamm changed after she drove to his apartment in Silver Lake, where he was living with four roommates. “When I got there, Jon was so sweet and he worked on these lines with me. I was like, ‘God, this guy is so talented...and so handsome!’” she admitted.
Jon Hamm and Jennifer Westfeldt stayed together as they rose to fame
While Hamm and Westfeldt initially met during the early days of their career, they stayed together while catapulting to fame. Westfeldt co-wrote her first film, ‘Kissing Jessica Stein’ in 2001, where Hamm had a small role and the former couple went on to establish a production company, Points West Pictures, together in 2009. Westfeldt also remained by Hamm’s side as he continued to skyrocket to success during the seven seasons of ‘Mad Men’.
Westfeldt made her directorial debut in the 2011 film ‘Friends with Kids’, in which she also starred alongside Hamm. “The hardest bit for people is that it [Don Draper from 'Mad Men'] is such an iconic character fans of the show have a really hard time imagining he is not like that. That he is really this goofball. And that he is in this long relationship. That is, I guess, why people come up and say all sorts of wildly inappropriate things to him, and me, which don’t bear repeating.” Westfeldt told The Guardian in 2012.
“People sometimes recognize me but can’t place me – it is always ‘Hi, we sat together at that wedding, table 11!’. With Jon, it’s just become this constant ‘OMIGODI’mgoingtodie!’ It’s like being with a Beatle or something,” she added. Speaking about his then-partner during the 2014 People Magazine Awards, Hamm said, “There’s another person who’s actually sitting in the audience who basically told me when I wasn’t working that I was still talented. And she’s stuck with me for the last 16 years, even if the talent question remains up for grabs.”
Hamm and Westfeldt also appeared together at several social and public events and graced numerous red carpets as a couple during their relationship. Reports suggest there were hardly any Hollywood events that the duo spent apart. “Our lives are entwined. It’s a long time [together]. I’m definitely the guy that repeats his stories! Mostly it’s just paying attention and keeping engaged and not succumbing to inertia or going through the motions,” Hamm told People in 2014.
Jon Hamm and Jennifer Westfeldt did not marry or raise children together
Despite having an 18-year-long relationship, Hamm and Westfeldt did not tie the knot and never raised children together. “I don’t have the marriage chip, and neither of us have the greatest examples of marriage in our families. But Jen is the love of my life, and we’ve already been together four times longer than my parents were married,” Hamm said in a 2010 interview with Parade.
“We may not have a piece of paper that says we’re husband and wife, but after 10 years, Jennifer is more than just a girlfriend. What we have is much deeper and we both know that. To me, people [should] get married when they’re ready to have kids, which I’m not ruling out,” the actor had previously explained in a 2008 interview with New York Post.
Speaking about having children together, Westfeldt told The Guardian in 2012, “But in reality our lives – Jon’s and mine – are so unconventional in every way, it’s very difficult. I think kids should have something grounded. Jon and I are both children of divorce. I’m not sure we can do it without a proper home base… We will see what happens. There at least are a lot of ways to procure a child these days.”
Jon Hamm and Jennifer Westfeldt parted ways in 2015
Hamm and Westfeldt left Hollywood in shock when they announced their split in 2015, after 18 years together. Just eight months before parting ways, the couple was seen beaming at HBO’s ‘Girls’ Season 4 premiere party at The American Museum of Natural History, in New York. In March 2015, Hamm completed his time in rehab to deal with alcoholism and received immense support from Westfeldt.
Meanwhile, the latter opened up about the impact of ‘Mad Men’ in Hamm’s real-life. “It’s a confusing juxtaposition. I think the darkness of Don has weight heavily on Jon, despite it being the role of a lifetime and the opportunity that gave him the career of his dreams,” Westfeldt told GQ in 2015. The pair was reportedly last seen together in New York in July that same year.
The now-former couple announced their split in an official statement provided to People. “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,” they wrote at the time.
