Jon Hamm’s new fiancee Anna Osceola cut a casual figure as she went on a dog walk in Los Angeles on Tuesday – one day after the pair’s engagement was revealed.
The 34-year-old redheaded beauty was dressed comfortably in an oversized red crew neck sweatshirt as she enjoyed a day of leisure, marking her first public outing since Jon, 51, popped the question.
The Massachusetts-born actress — who stepped out with her beau days ago — covered her eyes in a pair of dark aviator style sunglasses.
She wore dark sweatpants and slipped her feet into a pair of black and white striped slides.
Missing from the scene was her new fiancé, who recently popped the question, according to People.
Newly engaged! Jon Hamm’s new fiancee Anna Osceola cut a casual figure as she went on a dog walk in Los Angeles on Tuesday – one day after the pair’s engagement was revealed
They’re ENGAGED! Jon, 51, popped the question to Anna after two years of dating (pictured 2022)
Jon and Anna met when they co-starred on Mad Men in 2015, after Anna secured a small role as a receptionist named Clementine at Esalen, a spiritual California retreat that Jon’s character (Don Draper) attended in the final episode of the AMC series.
Things turned romantic during the 2020 quarantine, five years after he split from longtime partner Jennifer Westfeldt.
Osceola is best known for roles on Law & Order True Crime and Law & Order: Special Victims Unit, Greek, Rizzoli & Isles and NCIS.
In an appearance on Howard Stern in September 2022, the Baby Driver star said he could see himself getting married someday, after previously vowing it would never happen for him as he didn’t have the ‘marriage chip’ inside him.
‘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 said last year.
He added that he’s been able 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 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.’
Casual: The 34-year-old redheaded beauty was dressed comfortably in an oversized red crew neck sweatshirt
Shaded: The Massachusetts-born actress — who stepped out with her beau days ago — covered her eyes in a pair of dark aviator style sunglasses
The statements stand in stark contrast to comments he made in 2012, in which he revealed he didn’t believe in marriage and that he had no yearning to be a father.
He told the magazine, ‘I don’t have a driving force to have a baby. That said, I’m in a committed relationship, and if it ever came up, I’m not ruling it out.’
And about tying the knot he said, I don’t have a particularly defined example of marriage in my life.
‘My parents got divorced when I was two and never remarried. So it doesn’t mean anything to me.’
Jon continued, ‘I don’t mean to say that it shouldn’t mean things to other people. I’m not judging it one way or another.
How it started: The couple met on the series finale of Mad Men when Anna played Clementine, the receptionist at the wellness retreat Don Draper attended
‘It’s just my experience. I don’t have that paragon of married life to look at and think, “Oh yeah, that’s it! That’s what I want!”‘
The Emmy Award winner got candid when he said he has been seeking therapy in recent years and has found that a lot of his trauma comes from losing his mother to colon cancer when he was just ten-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.’
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