Jon Hamm, 51, and his new fiancée Anna Osceola, 34, look smitten as they step out for dinner

Jon Hamm and his new fiancée Anna Osceola looked smitten as they went out for dinner in Los Angeles recently – days before their engagement was announced.

The Mad Men star, 51, and his actress love, 34, strolled arm in arm after a sushi dinner – before it was revealed he popped the question to her after two years of dating .

Hamm wrapped up in a cream sweater and suede jacket, paired with jeans and trainers as he strolled with his partner.

Anna wore a yellow swear word, paired with a sheepskin coat as she left the restaurant.

Her hair was styled in soft waves and she sported a radiant makeup palette.

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, after swearing it would never happen for him because he didn’t have the “chip of marriage” in him.

“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 interview was in stark contrast to comments he made in 2012, where he revealed he adamantly does not believe in marriage and has no desire to be a father.

He told the magazine, “I don’t have a driving force to have a baby.”

Before adding, “Having said that, I’m in a committed relationship, and if that ever happens, I’m not ruling it out.”

But he is even more strident about marriage.

“I don’t have a particularly defined example of marriage in my life,” he said.

Before adding: “My parents divorced when I was two years old and never remarried. So that means nothing to me.

He concluded, “I don’t mean it shouldn’t mean things to other people. I don’t judge him one way or another.

‘It’s just my experience. I don’t have this paragon of married life to look at and think, ‘Oh yeah, right! That’s what I want!”

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.”

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.