Jon Hamm is engaged to Anna Osceola after two years of dating

They’re ENGAGED! Mad Men star Jon Hamm, 51, pops the question to Anna Osceola, 34, after two years of dating

Jon Hamm and Anna Osceola are engaged. 

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

The pair first met when they co-starred on Mad Men in 2015, after Anna bagged a small role as the receptionist named Clementine at Esalen, a spiritual California retreat that Jon’s character (Don Draper) attended in the final episode of the AMC series. 

At the time, Jon was in an 18-year long relationship with Jennifer Westfeldt during which both 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 – have been spotted together dating as far back as 2017 but rumors of their romance really took off in 2020 when the pair were repeatedly spotted running errands together during the coronavirus lockdown.

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

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

‘This is all part of what I’m saying,’ Jon said at the time. ‘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 added that that he’s been able to sit down to start ‘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,’ he continued. ‘What else is there other than that?’

During that interview, the Bridesmaids actor also said that he was ‘very much in love.’ 

The Emmy Award winner was open as he revealed that he has been seeking therapy over the past few years and has found that a lot of his trauma comes from losing his mother to colon cancer when he was just 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 of that trauma and realizing 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 availability and vulnerability.’

Two years: The couple met in 2015 but didn’t confirm their romance until 2020

Changed view: The Baby Driver star credits therapy with getting him to a mental place where he is ready to get married

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

They also attended the 2022 ESPYs together, where they packed on the PDAs on the red carpet.

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

The Black Mirror actor took on the role of Irwin M. Fletcher – which was 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 on Law & Order True Crime and Law & Order: Special Victims Unit, Greek, Rizzoli & Isles, and NCIS. 

The Top Gun: Maverick and his lady love keep their private lives private and don’t have a social media presence. 

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

Where it all began: The couple met on the series finale of Med Men 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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