Jon Hamm and Anna Osceola have been dating for two years, and they are prepared to marry.
After first dating in 2020, the Confess, Fletch co-stars are now engaged, according to People. The two actors actually first crossed paths in 2015 on the set of Mad Men, where Osceola portrayed Clementine, the receptionist at the spiritual retreat Don Draper checks into, and Hamm played Don Draper, the show’s main character.
But, since Hamm was still seeing his longterm girlfriend Jennifer Westfeldt when the two first met, things didn’t get passionate between them until five years later. Just a few months after, he and Westfeldt split up. after 18 years of collaboration, the end of the show.
After being seen together multiple times throughout the pandemic, rumours of a relationship between Hamm and Osceola surfaced in 2020. And when the couple went on vacation to Italy in September 2021, it was almost certain that they were dating.
They declared their relationship public on the red carpet at an Oscars afterparty in March 2022, and they then made a second step-and-repeat appearance together in May at the Bedwetter movie premiere.
ALSO READ: IN A THREE-TEAM DEAL INVOLVING THE COYOTES, THE RANGERS ACQUIRE F KANE FROM THE BLACKHAWKS.
Although Hamm and Osceola have kept their relationship very discreet, the The Town actor did admit that Osceola has prompted him to consider marriage and having children for the first time.
“All of this is included in what I’m saying. There is another site in my life that I feel quite settled and content. I’m in a relationship right now and it’s comfortable,” he remarked during a September 2022 appearance on Howard Stern’s SiriusXM show. “It’s a sensation of taking care of someone else and being taken care of.”
He went on to explain that the success of their relationship is the result of “a process of working on myself, my mental health, all the stuff with my therapist and unpacking all of that trauma and realising that when you lose someone that’s so important to you, like a mother, so early, that that creates a wound that blocks a lot of that emotional accessibility.
That blocks a lot of that openness and vulnerability.” Hamm lost his mother when he was 10 years old to colon cancer, and his father died ten years after that. He continued, “It’s only been in the last couple of years, me kind of sitting down and 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.” Hamm said, “That sounds cheesy and whatever, but it’s real and it’s—for want of a better word—what it’s I’m striving towards. What more is there other than that?” He also acknowledged that he is “very much” in love.
ALSO READ: Stand-up comedian and TV investigator Richard Belzer passes away at age 78.