After three years together, Jon Hamm and Anna Osceola are apparently engaged. Monday’s issue of People verified the story, however, a representative for the actor did not immediately return Page Six’s request for comment.
The cast of “Confess, Fletch” originally worked together in 2015 for the premiere of “Mad Men’s” series finale. Despite multiple sightings of Hamm, 51, and Osceola, 34, in early 2020, they were not romantically linked until later in the year.
These two private people were seen playing tennis in May and then relaxing on a California beach in September. Neither of them uses any form of social media. They had kept their romance low-key, but in September of 2021, they were caught engaging in some major PDA while on vacation in Italy.
In March 2022, the actor from “Top Gun: Maverick” and the actress from “Law & Order True Crime” made their red carpet debut as a pair at the Mercedes-Benz Academy Awards viewing party and the Vanity Fair annual afterparty.
As of last September, Hamm told Howard Stern that he “could for certainly” envision himself spending the rest of his life with Osceola and that he was “very much” in love with her.
He gushed at the time, explaining that the actress had “opened up the possibility of things like being married, having kids, you know, defining a new version of happiness, life, wellness,” which he described as “good and comfortable, and it’s feeling about taking care of someone else and being taken care of.”
In addition, he stated, “All that stuff sounds cheesy and whatever, but it’s genuine. And, for lack of a better expression, that is the goal toward which I am striving. I mean, other than that, what else is there?
Moreover, Hamm said that Osceola had a crucial role in the “process of working on [himself],” which included “unpacking” the trauma of losing his mother when he was 10 years old.
When Did They Get Engaged?
An engagement between Jon Hamm and Osceola was announced on February 27, 2023, as reported by PEOPLE. They’ve supposedly been together since the year 2020.
But, at the 2022 Vanity Fair Oscar Party, the 51-year-old actor and his then-girlfriend made their relationship red carpet public. PEOPLE reports that the pair met in 2015 on the set of the AMC show Mad Men.
In the final episode, Osceola played the receptionist at the meditation retreat where Jon Hamm’s Don Draper spent time.
Their romance was a closely guarded secret until the day of their red carpet-presentation. Many public appearances by the Hollywood couple have been documented, including dog walks and trips to the California coast.
Do you know which well-known personalities recently tied the knot? You can click on the following links to find out more about their marital status:
- Who is Rebel Wilson’s Girlfriend? Is She Engaged to Ramona Agruma?
- Billy Ray Cyrus Is Engaged And Opens Up On Relationship With Fiancée Firerose
Hollywood Life Confirmed on Twitter That Jon Hamm is Reportedly engaged to his girlfriend Anna Osceola
— HollywoodLife (@HollywoodLife) February 28, 2023
Who Has Jon Hamm Dated?
Jon Hamm, whose real name is Jonathan Daniel Hamm, became famous for playing Don Draper on the Emmy-winning series Mad Men. Osceola is Hamm’s third girlfriend; he previously dated Jennifer Westfeldt, an actress.
After dating on and off since 1997, Westfeldt and Hamm finally called it quits in 2015. They added in a joint statement, “We will continue to be supportive of each other in every manner imaginable moving forward.”
Do you know which famous people recently engaged? These are some links you can visit to learn more about their personal life: