Jon Hamm 'engaged to Mad Men co-star' after two years of dating

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Jon Hamm has reportedly proposed to Anna Osceola (Image: 2022 WireImage)
Jon Hamm has reportedly proposed to Anna Osceola (Image: 2022 WireImage)

Jon Hamm is engaged to his girlfriend Anna Osceola after two years of dating, according to reports.

The loved-up couple first met when they co-starred in Mad Men in 2015, when Anna appeared as a receptionist at the spiritual retreat Jon's character attended in the final episode of the series.

51-year-old Jon and Anna, 34, started dating in 2020 and Jon recently gushed about how much he is in love with Anna.

The actor said he is "very much" in love with Anna and that their relationship is "meaningful". He also revealed he is open to the possibility of getting married and having kids.

"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," Jon said.

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Jon Hamm 'engaged to Mad Men co-star' after two years of datingJon is thought to have popped the question (2022 WireImage)

He added 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.

"What else is there other than that," he said during an appearance on SiriusXM back in September.

Jon Hamm 'engaged to Mad Men co-star' after two years of datingThe pair have been dating for two years (2022 Michael Kovac)

According to People, Jon's dreams are one step closer as he and Anna are now set to tie the knot.

Before Anna, Jon was in a long-term relationship with actress and screenwriter Jennifer Westfeldt from 1997 until their split in 2015.

Jon and Anna, who both keep off social media, were first photographed together in 2017.

Since their relationship heated up and went public, they've been spotted stepping out for meals, playing tennis and enjoying a day at the beach.

They also took a holiday to Italy together in September 2021.

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

They also reunited on-screen in the third instalment of the Fletch franchise, Confess, Fletch last year. In the film, Jon took on the role of Irwin M. Fletcher and Anna played Larry.

Jennifer Aniston strips naked in steamy scene with Jon Hamm on The Morning ShowJennifer Aniston strips naked in steamy scene with Jon Hamm on The Morning Show

Scarlett O'Toole

Mad Men, Jon Hamm

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