“Mad Men” Costars Jon Hamm and Anna Osceola Are Reportedly Engaged

Jon Hamm and Anna Osceola are reportedly taking their romance to the next level. On Feb. 27, People confirmed that the pair are engaged after two years of dating. No other details about the couple’s engagement are known at this time, and neither has commented on their latest relationship milestone. Reps for the “Mad Men” costars did not immediately respond to POPSUGAR’s request for comment.

It’s believed that Hamm and Osceola first met on the set of their AMC series back in 2015, according to People. However, the couple didn’t spark dating rumors until the summer of 2020 after they were spotted out together on numerous occasions. Us Weekly confirmed their romance that June and the two have been low-key about their relationship ever since.

With the exception of a number of outings at the start of their romance and joint appearances at Hollywood events in the last two years, the “Confess, Fletch” stars rarely discuss their relationship publicly and both stay off of social media. However, in September 2022, Hamm did tell Howard Stern on his SiriusXM show that he could see himself getting married someday.

“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,” he told the host, also noting then that he’s “really 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.”

“It sounds hokey and whatever, but it’s real and for one of a better word, it’s what I’m working for,” Hamm added. “What else is there other than that?”

Not much is known about Osceola’s dating history but before his relationship with the actor, Hamm was in a long-term relationship with Jennifer Westfeldt. They then separated in 2015 after 18 years together, per People.