Jon Hamm was always the right man to play Don Draper on “Mad Men” — even if it took producers a while to realize that. They wanted someone more famous, and Hamm wasn’t exactly that. Hamm’s not even sure how many times he had to audition to convince Matthew Weiner and company that he had a fair amount of Don Draper in his veins, he told The Times in 2009.
Hamm practically grew up with one. “My father was a businessman in the 1960s,” Hamm said, explaining that they hail from small, conservative St. Louis, Missouri. “And my father was originally a big fish in this little pond.” His old man worked in the trucking company, so he dabbled in some interesting characters. “He worked with the mafia and the team stars [union]. It wasn’t a timid affair,” he added. Although his childhood provided a wealth of materials for building the perfect character for Mad Men, Hamm is not his father. He’s not the shy don either.
Hamm is as monogamous as they come. Hamm devoted most of his life to a single partner. He met Jennifer Westfeldt at a party in 1997, around the time she was writing “Kissing Jessica Stein,” which he starred in, according to the New York Post. Hamm and Westfeldt forged a strong relationship that lasted almost two decades until they went their separate ways in 2015, Entertainment Tonight reported. But in the 18 years they were together, Hamm and Westfeldt never tied the knot. Hamm had his reasons.
Jon Hamm believes marriage is for specific purposes
Jon Hamm didn’t need a document to confirm his relationship with Jennifer Westfeldt. “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 friend,” Hamm told the New York Post in 2008. “What we have is much deeper and we both know it.” According to Hamm, marriage serves socially valid purposes that have nothing to do with love or partnership, but with practical things in life. “For me, folks [should] marry when they are ready to have children, which I don’t rule out,” he added. But that never happened and Hamm has remained childless — and unmarried.
Aside from his views on the bureaucracy of marriage, Hamm also didn’t want to risk what he had with Westfeldt. “Jen is a wonderful observer of the human condition and we’ve watched a lot of our friends going through what the people in the film are going through,” he told The Sydney Morning Herald in 2012. If it’s not broken, is it? Hollywood wasn’t the only place he’d seen marriages fall apart almost as quickly as the whirlwind romances that usually preceded them.
Even his small-town upbringing had enough of it. For starters, his own mother and father divorced when he was just 2, The Guardian noted. Hamm knew that signing some papers was no guarantee of a lasting relationship. “We’ve been together four times longer than my parents were married,” he told Parade.
Jon Hamm is now in another committed relationship
The bachelor life wasn’t Jon Hamm’s. “It’s hard to be single after being together for a long time. It’s really hard. It sucks,” Hamm told InStyle in 2017. But that wouldn’t be long now. That year, Hamm was spotted leaving a coffee shop with Anna Osceola, though similar sightings didn’t become more common until 2020, according to Extra. By this point, the two actors were already a topic, Us Weekly reported. Hamm and Osceola met in 2015, the same year he split from Jennifer Westfeldt, according to People. Osceola had a small role in the “Mad Men” finale, playing a receptionist at the spiritual retreat Don Draper found himself at.
It’s unclear if they formed a friendship at the time or later reconnected, but their relationship really gained momentum during the COVID-19 pandemic when they were constantly spotted together. In May 2020, Hamm and Osceola played tennis in Los Angeles, the Daily Mail noted, just months after People reported the couple enjoying breakfast on the town. By September 2021, their relationship was looking pretty solid when they headed to Italy for a vacation, according to Page Six.
While opting to keep their romance private, Hamm and Osceola made their public debut in March by attending an Oscars after-party together, according to People. They have since attended other events (the one pictured above is in July) which show Hamm’s single man days are indeed behind him.