Jon Hamm Has Recently Announced His Engagement to his Former Co-Star

Congratulations are in order for Jon Hamm and Anna Osceola – the Mad Men star is reportedly engaged to his leading lady! The pair first crossed paths when Osceola starred alongside him in one of the final episodes of Mad Men, “Person to Person”, back in 2015. Most recently, she also had a part in Hamm’s hilarious movie Confess, Fletch.

After two blissful years of courtship, Hamm and Osceola finally got engaged in 2020! The lovebirds made their romantic debut as a couple at an Oscars afterparty in March 2022. It was shortly followed by more glamourous moments like the red carpet for Sarah Silverman’s musical Bedwetter, ESPY Awards, and Confess Fletch screening. At 51 years old and 34 respectively, this couple is proving that age is just but a number when it comes to true love!

Osceola famously had a minor role in the finale of Mad Men, as a receptionist at Don Draper’s spiritual retreat. Prior to this stint on the show, Hamm was involved in an 18-year union with Jennifer Westfeldt that sadly fell apart in 2015. Since then, he has been seen out and about with Osceola only once back 2017 – although unconfirmed by either party themselves through social media channels – yet paparazzi have managed to capture them together several times over the past two years!

Last year, Hamm took lead roles in the movie adaptation of Gregory McDonald’s 1976 novel Confess, Fletch – taking over from Chevy Chase as Irwin M. “Fletch” Fletcher. It was directed by Greg Mottola and received rave reviews despite its brief theatrical run time; with Osceola also making a small appearance. In addition to this film, Osceola has had guest appearances on TV shows such as Saving Grace, Greek, Rizzoli & Isles, Bull Law & Order: Special Victims Unit and more!

During his visit to Howard Stern‘s SiriusXM show in September 2022, Hamm revealed that he was now ready for marriage as it had become an attractive reality. “This is all part of what I’m saying. This is another place in my life that I feel very settled and comfortable. I’m in a relationship right now and it’s comfortable,” Hamm said at the time. He noted how he can begin “thinking about all that stuff, that’s made the relationship that I’m in now even more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness.” Hamm later told Stern he is “very much so” in love.

After eight years of being nominated, Jon Hamm finally won an Emmy for his role as Don Draper in the popular TV series Mad Men. Following this success, he was casted to play Admiral Beau “Cyclone” Simpson in Top Gun: Maverick and will soon be featured on Apple TV’s The Morning Show Season 3 as well as Fargo‘s 5th installment. These opportunities highlight Jon Hamm’s impressive acting talent and are a testament to his remarkable career achievements thus far!