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How Jon Hamm finally made it down the aisle after vowing to NEVER marry during 18-year relationship

Jon Hamm and his wife Anna Osceola, who he wed on Saturday during a star-studded ceremony, famously met on the series finale back in 2015, the same year he ultimately ended his 18-year relationship with Jennifer Westfeldt. 

During his past relationship, which spanned nearly two decades, the 52-year-old was adamant that he would never tie the knot as he stated that he didn’t ‘have a particularly defined example of marriage.’

‘My parents got divorced when I was two and never remarried. So it doesn’t mean anything to me,’ he said during a 2012 interview with Playboy. ‘I don’t mean to say that it shouldn’t mean things to other people. I’m not judging it one way or another.’

The star continued: ‘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!” 

Additionally, he stated that he did not have ‘a driving force to have a baby.’ 

Still, he wasn’t completely opposed to becoming a father as he said he wasn’t ‘ruling it out.’ 

Change of heart: Jon Hamm and his wife Anna Osceola, who he wed on Saturday during a star-studded ceremony, famously met on the series finale back in 2015, the same year he ultimately ended his 18-year relationship with Jennifer Westfeldt

Past love: During his past relationship, which spanned nearly two decades, the 52-year-old was adamant that he would never tie the knot as he stated that he didn't 'have a particularly defined example of marriage' (seen in 2014)

Past love: During his past relationship, which spanned nearly two decades, the 52-year-old was adamant that he would never tie the knot as he stated that he didn’t ‘have a particularly defined example of marriage’ (seen in 2014)

Just months after meeting Osceola on set of Mad Men, Hamm and Westfeldt announced they ended their longtime relationship. 

With great sadness, we have decided to separate, after 18 years of love and shared history,’ they told ET in a joint statement. We will continue to be supportive of each other in every way possible moving forward.’ 

At the time, a source told the outlet that Hamm’s ‘party-heavy lifestyle’ had become too much for Westfeldt. 

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‘Jon and Jennifer really fought hard to make their relationship work, Jennifer more so than Jon,’ the source revealed. ‘They were together for many years, but in the end, it was too much work. It’s no secret that Jon likes to go out and leads a very party-heavy lifestyle. And Jennifer was just tired of that.’ 

Additionally, it was claimed Westfeldt wanted him ‘to grow up’ but ‘he never wanted to.’

Ultimately, she became sick of ‘being his mother.’

Eight years after their split, however, he managed to finally walk down the aisle with Osceola, who is 17 years his junior.

The newlyweds reportedly began dating in 2020, five years after they were introduced on the set of his AMC show, which ran from 2007 to 2015.

Fateful meeting: Osceola portrayed Clementine, the receptionist at a spiritual retreat that Hamm's character, Don Draper, was attending

Fateful meeting: Osceola portrayed Clementine, the receptionist at a spiritual retreat that Hamm’s character, Don Draper, was attending

Forever and always: Osceola (seen above) is 17 years younger than her husband

Forever and always: Osceola (seen above) is 17 years younger than her husband

Osceola 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 hit series.

The couple 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.’

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‘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?’

Shocking end: Just months after meeting Osceola on set of Mad Men, Hamm and Westfeldt announced they ended their longtime relationship; seen in 2015

Shocking end: Just months after meeting Osceola on set of Mad Men, Hamm and Westfeldt announced they ended their longtime relationship; seen in 2015

His bride: Eight years after their split, however, he managed to finally walk down the aisle with Osceola, who is 17 years his junior; seen in March 2023

His bride: Eight years after their split, however, he managed to finally walk down the aisle with Osceola, who is 17 years his junior; seen in March 2023

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

In February, news broke that he proposed to Osceola. 

Westfeldt, 54, is reportedly single, but previously spoke about not having children during her relationship with Hamm in 2012.

‘We don’t [have children]. It’s always on the periphery of the discussion, but we do not have children,’ she said when asked about having kids. 

‘You know, it’s a tricky balance to strike. And I have a tremendous amount of respect for my friends who do balance this particular career with raising a kid, Because it’s a tricky environment to bring them into. So not for us just yet,’ she said. 

At the time, she told The New York Times that she ‘never’ thought she would ‘be this age and not have kids.’ 

‘But my life has also gone in a million ways I never anticipated,’ she noted. 

Westfeldt concluded: ‘I kept feeling like I’d wake up with absolute clarity, and I haven’t. And we have a pretty great life together. The chance that we’ll regret it doesn’t seem like a compelling enough reason to do it. I may wake up tomorrow with that lighting bolt, and I’ll have to scramble to make it happen.’

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