View gallery
Image Credit: Stephen Lovekin/Shutterstock
Jon Hamm’s dating history is the opposite of his lengthy acting career — it’s short and sweet! The former star of Mad Men is currently married to his wife, Anna Osceola, and was previously linked to his ex and longtime partner, Jennifer Westfeldt. Before meeting Anna, Jon was known for leaning away from the idea of marriage.
In 2012, the Top Gun: Maverick actor told Playboy that he didn’t have plans to exchange vows with anyone. “I don’t have a particularly defined example of marriage in my life,” he told the publication. “My parents got divorced when I was 1 and never remarried. So, it doesn’t mean anything to me. … I don’t have a driving force to have a baby. That said, I’m in a committed relationship, and if it ever came up, I’m not ruling it out.”
Learn more about Jon’s wife, Anna, and his former partner, Jennifer, below!
Jennifer Westfeldt
Mediapunch/Shutterstock
Jon and Jennifer first met at a mutual friend’s birthday party while they were both actively auditioning, he told The Hollywood Reporter in 2011.
“[It was a] completely random meeting,” the Mean Girls musical movie star explained. “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 and wanted to read with somebody who was a guy, and she didn’t really know any guys out here, so she called [me]. Apparently I wasn’t very good, ’cause she didn’t get the part.”
Throughout their 18-year relationship, the former pair publicly spoke about how they maintained a long-term romance. As working actors, they both had to juggle hectic schedules and agreed to support one another in whatever job they could land.
During a 2012 interview with The New York Times, Jon explained that he and Jennifer would always try to figure out how to move forward if they had to spend time apart for a new gig.
“When Jen gets a big part on Broadway, and I’ve known her long enough to know that’s something she’s wanted to do since first grade, I’m not going to be like, ‘Well, I’m on a TV show, so who’s going to take care of the dog? Who’s going to hang out?’” Jon noted at the time. “It’s like, ‘You’re going to go to Broadway, and we’ll figure it out.’ And the opposite is true.”
Although they enjoyed a durable years-long love, Jon and Jennifer split in 2015. The duo released a joint statement at the time, breaking their silence about their breakup.
“With great sadness, we have decided to separate after 18 years of love and shared history,” their statement read, per Entertainment Tonight. “We will continue to be supportive of each other in every way possible moving forward.
Jon later spoke with InStyle 2017 about the aftermath of their breakup, noting that it “sucks” being single after being with someone he loved for a long time.
“It’s hard,” he noted. “It’s hard to be single after being together for a long time. It’s really hard. It sucks.”
Anna Osceola
Virisa Yong/BFA.com/Shutterstock
After meeting on the set of Mad Men in 2015, Jon and Anna officially started dating in 2020. Three years later, they were engaged and tied the knot in a cliffside ceremony in Big Sur, California, in June 2023.
Jon opened up about getting married during his appearance on Jimmy Kimmel Live! In November 2023, calling their wedding “very exciting.”
“We did it this summer in beautiful Big Sur,” the Fargo star explained It was a perfect day. It was very sparsely attended, by our decision; it was small. And man, it was great.”
