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Jon Hamm and his new fiancée Anna Osceola coordinated on the red carpet while attending the Vanity Fair Oscar Party in Los Angeles on Sunday.
The Mad Men star, 52, was dapper as ever in a classic black tuxedo and bowtie, while the Conspiracy actress, 34, dazzled in a classy black and white one-shoulder gown at the bash celebrating the 95th Annual Academy Awards.
The beauty wore her brunette tresses parted in the middle and cascading down, and accessorized with a green clutch.
It was the first red carpet outing for the couple since the announcement of their engagement last month.
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.
Dazzling pair: Jon Hamm and his new fiancée Anna Osceola coordinated on the red carpet while attending the Vanity Fair Oscar Party in Los Angeles on Sunday
Vanity Fair’s Oscar Party – which celebrates Hollywood’s biggest night and is considered one of the most exclusive post-Oscar parties – is hosted by Vanity Fair editor-in-chief Radhika Jones.
At the time of the couple’s meeting, Jon was in an 18-year long relationship with Jennifer Westfeldt, 53, during which both frequently said they never wanted to get married. They broke up in 2015.
Jon and Anna 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, after previously vowing it would never happen for him as he didn’t have the ‘marriage chip’ inside him.
‘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.’
Classy: The Mad Men star, 52, was dapper as ever in a classic black tuxedo and bowtie, while the Conspiracy actress, 34, dazzled in a classy black and white one-shoulder gown
Newly engaged: It was the first red carpet outing for the couple since the announcement of their engagement last month
Stunner: The beauty wore her brunette tresses parted in the middle and cascading down, and accessorized with a green clutch
Where they made their debut: The couple made their red carpet debut in 2022, when they attended the Vanity Fair Oscars after party together
The interview was in stark contrast to comments he made in 2012, where he revealed he categorically doesn’t believe in marriage and that he has no yearning to be a father.
He told the magazine: ‘I don’t have a driving force to have a baby.’
Before adding: ‘That said, I’m in a committed relationship, and if it ever came up, I’m not ruling it out.’
But he’s even more vehement on the subject of marriage.
‘I don’t have a particularly defined example of marriage in my life,’ he said.
Before adding: ‘My parents got divorced when I was two and never remarried. So it doesn’t mean anything to me.’
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.
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
The ex: 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; Pictured 2014
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