Jon Hamm engaged to Anna Osceola

Jon Hamm and Anna Osceola are engaged.

The 51-year-old star reportedly popped the question to actress Anna, 34, PEOPLE reports.

The pair first met when they starred in Mad Men in 2015, after Anna landed a small role as a receptionist named Clementine at Esalen, a Californian spiritual retreat at which Jon’s character ( Don Draper) assisted in the final episode of the AMC series.

At the time, Jon was in an 18-year relationship with Jennifer Westfeldt during which the two frequently said they never wanted to get married.

They broke up in 2015.

Jon and Anna – who were spotted in the Hamptons walking their dog – were spotted together as early as 2017, but romance rumors really took off in 2020 when the pair were spotted doing shopping together during the coronavirus lockdown.

During an appearance on Howard Stern in September 2022, the Baby Driver star said he could see himself getting married one day.

They are ENGAGED! Jon Hamm, 51, popped the question to girlfriend Anna Osceola, 34, after two years of dating

“It’s all part of what I say,” Jon said at the time. “It’s another place in my life where I feel very settled and comfortable. I’m in a relationship right now and it’s comfortable.

He added that he was able to sit down and start “really thinking about all of this, it made the relationship that I’m in even more meaningful and opened up the possibility of things like being married, having children, defining a new version of happiness, of life, of well-being.’

“It sounds hokey and whatever, but it’s real and for a better word, it’s what I work for,” he continued. ‘What else is it?’

During this interview, the Bridesmaids actor also said he was “very much in love.”

The Emmy Award winner was open when he revealed he had been seeking therapy for the past few years and discovered that much of his trauma stemmed from the loss of his mother to breast cancer. colon when he was only 10 years old.

“It’s also been a process of working on myself, my mental health, all the stuff with my therapist,” he said.

“And unpacking all that trauma and realizing that when you lose someone who is so important to you, like a mother, so soon, it creates a wound that blocks a lot of that emotional accessibility.

“It blocks a lot of that availability and that vulnerability.”

Two years: the couple met in 2015 but did not confirm their romance until 2020
Change of view: Baby Driver star credits therapy with getting him to a mental place where he’s ready to get married

The couple made their red carpet debut in 2022 when they attended Vanity Fair’s Oscars after-party together.

They also attended the 2022 ESPYs together, where they got riled up on the PDAs on the red carpet.

And Jon and Anna also reunited on screen for the first time since the 2022 Mad Men finale in the third installment of the Fletch franchise, Confess, Fletch.

The Black Mirror actor took on the role of Irwin M. Fletcher, originally played by Chevy Chase in the 1985 and 1989 films.

Anna played the role of Larry in the film.

Osceola is best known for her roles in Law & Order True Crime and Law & Order: Special Victims Unit, Greek, Rizzoli & Isles and NCIS.

The Top Gun: Maverick and his sweetheart keep their personal lives private and are not present on social media.

“The point of life is not to put on dog ears and post it online for everyone to see,” he told InStyle in 2017.

Where it all started: The pair met in the Med Men series finale when Anna played Clementine, the receptionist at the wellness retreat Don Draper attended
Red carpet official: The two made their first red carpet appearance as a couple at the 2022 Vanity Fair Oscar Party

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