A match made in Mad Men: FEMAIL reveals how Jon Hamm DUMPED his girlfriend of 18 YEARS after meeting fiancee Anna Osceola on the set of his TV hit – and how she convinced him to U-turn on his anti-marriage stance

• Jon, 51, met Anna, 34, eight years ago – while he was dating Jennifer Westfeldt
• Soon after they met, he and Jennifer split after 18 years together
• He and Anna started dating in 2020, and they’re now gearing up to get married 

The show Mad Men changed Jon Hamm’s life in many ways. Not only did it propel him into the spotlight and help launch a major career for the actor, but it also brought his future-wife into his life.

Jon, 51, met Anna Osceolo, 34, eight years ago when she appeared in one episode of the popular AMC show as a receptionist.

When their paths first crossed, Jon was in a loving relationship with actress Jennifer Westfeldt – but just months after he met Anna, news hit the web that he and Jennifer had split after a whopping 18 years together.

While nobody thought that his Mad Men costar had anything to do with his and Jennifer’s breakup at the time, when he and Anna became romantically involved years later, the suspicious timing left some people wondering: did Anna have anything to do with the dissolvement of Jon and Jennifer’s romance?

Not only did the show Mad Men help launch a major career for the actor, but it also brought his future-wife, Anna Osceolo, into his life. They are seen in the show

When their paths first crossed, Jon was in a relationship with Jennifer Westfeldt – but just months after he met Anna, he and Jennifer split after a whopping 18 years together

Whether Anna had an impact on the split or not, it was clear that there was a strong connection between her and Jon because they eventually went on to fall madly in love – however, it wouldn’t be until many years later.

Reports of Jon and Anna’s romance first emerged in May 2020, and soon after news hit the web that they were dating, the two quickly started flaunting their love for the whole world to see.

Jon and Anna started dating five years later. They are now engaged, and as the couple prepares to become husband and wife, FEMAIL went ahead and recapped their entire relationship from start to finish

They were seen packing on the PDA, jetting off on lavish getaways together, and attending red carpet events side-by-side – and Anna even managed to change the actor’s negative stance on marriage.

Jon previously admitted that he had no interest in ever walking down the aisle, but in a 2022 interview with Sirius XM, he revealed that everything had changed once Anna came into his life.

He credited her with inspiring him to get therapy for the trauma he endured as a child following the death of his mother – which ultimately gave him a newfound drive to become a family man.

Now, Jon and Anna are officially gearing up to become husband and wife – with Us Weekly confirming their engagement earlier this week.

As the couple prepares to exchange vows, 13 years after Jon swore he’d never settle down, FEMAIL went ahead and recapped their entire relationship from start to finish.

To their first meeting on set of Mad Men all those years ago and the truth about his split from Jennifer to how Anna convinced Jon to make a complete 360 on his plans to never marry – here’s a look back at everything the pair has been through together. 

Jon and his girlfriend-of-18-years split soon after he and Anna met on set of Mad Men in 2015 – but they didn’t officially start dating until five years later

Jon and Anna – who is originally from Cambridge, Massachusetts – met on set of the show Mad Men in 2015, five years before they started dating

Jon and Anna – who is originally from Cambridge, Massachusetts – met on set of the show Mad Men in 2015, five years before they started dating.

Jon played protagonist Don Draper in the AMC series, while Anna appeared as Clementine (seen), a receptionist who worked at a retreat that Don visited in one episode of the last season

Jon played protagonist Don Draper in the AMC series, while Anna appeared as Clementine, a receptionist who worked at a retreat that Don visited in one episode of the final season. 

When they first met, the actor was in a long-term relationship with Jennifer – however, they split soon after he crossed paths with Anna, after 18 long years together.

‘With great sadness, we have decided to separate, after 18 years of love and shared history,’ the couple said in a joint statement.

‘We will continue to be supportive of each other in every way possible moving forward.’

At the time, there was rumors that Jon’s ‘party-heavy lifestyle’ was to blame – he had recently completed a 30-day stint in rehab for alcoholism – but now that he and Anna are together, the question remains: did she have anything to do with the breakup? 

Jon and Jennifer (seen in 2015) split in September 2020 and now that he and Anna are together, the question remains: did she have anything to do with the breakup?

Whether Anna had an impact on the breakup or not, it was clear that there was a strong connection between her and Jon because they eventually went on to fall madly in love

‘Jon and Jennifer really fought hard to make their relationship work, Jennifer more so than Jon,’ a source told ET at the time.

‘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. 

‘Jennifer was just tired of that. She wanted him to grow up … and he never wanted to. She was tired of being his mother.’

Whether Anna had an impact on the breakup or not, it was clear that there was a strong connection between her and Jon because they eventually went on to fall madly in love – however, it wouldn’t be until many years later.

Though there were brief rumors that they were dating in 2017, after photos emerged of them exiting a coffee shop together, that seemed to quickly fizzle out.

Jon was then linked to a slew of other famous faces like actress and comedian Jenny Slate and Saturday Night Live producer Lindsay Shookus.

After confirming their romance in 2020, Jon and Anna were often seen packing on the PDA and jetting off on lavish getaways – but they stayed tight-lipped about the details surrounding their relationship

In May 2020, after Jon and Anna were spotted playing tennis together, rumors started to swirl that they were an item. Us Weekly confirmed that they were indeed dating one month later

After news of their romance hit the web, Jon and Anna quickly started flaunting their love for the whole world to see. They are pictured in March 2022

In May 2020, after Jon and Anna were spotted playing tennis together, rumors quickly started to swirl that they were an item again.

Us Weekly confirmed that they were indeed dating one month later, and the pair quickly became inseparable.

They hit the beach in Santa Barbara, California, together in September 2020, jetted off on a romantic getaway in Italy in September 2021 (seen), started attending red carpet events side-by-side in March 2022, and acted together in the movie Confess, Fletch, in September 2022

After news of their romance hit the web, Jon and Anna quickly started flaunting their love for the whole world to see.

They hit the beach in Santa Barbara, California, together in September 2020, jetted off on a romantic getaway in Italy in September 2021, started attending red carpet events side-by-side in March 2022, and acted together in the movie Confess, Fletch, in September 2022. 

While the couple were not shying away from cameras, they still stayed pretty tight-lipped about the details surrounding their romance.

They hardly ever spoke about one another in interviews, and neither of them use social media, leaving much of their relationship shrouded by mystery. 

‘The point of life is not to put dog ears on yourself and post it online for everyone to see,’ Jon once said to InStyle about social media.

‘It’s fun, it’s adorable, but it’s the visual equivalent of masturbating – there’s no point other than immediate gratification.’

Anna ultimately changed Jon’s negative view on marriage – and the two got engaged 13 years after he said he didn’t think he’d ever be interested in walking down the aisle

While the couple were not shying away from cameras, they still stayed pretty tight-lipped about the details surrounding their romance

In September 2022, however, the actor discussed his and Anna’s love for the first time a rare chat with Sirius XM – and he revealed that he was reconsidering his stance on marriage, after spending years thinking that he would never be interested in walking down the aisle.

In September 2022, however, the actor discussed his and Anna’s love for the first time a rare chat with Sirius XM – and he revealed that he was reconsidering his stance on marriage, after spending years thinking that he would never be interested in walking down the aisle

‘[I’m in] another place in my life where I feel very settled and comfortable. I’m in a relationship right now and it’s comfortable,’ he said.

The star added that he recently became focused on improving his mental health and substance abuse issues through therapy – after spending years struggling with the trauma he faced as a child, after losing his mother to colon cancer at age 10.

He said getting professional help ‘opened up the possibility of things like being married and having kids.’

‘I’ve been 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,’ he continued.

‘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?’

In 2010, while Jon was still dating Jennifer, he first revealed that neither he, nor his girlfriend, had any interest in tying the knot.

He credited Anna with inspiring him to get therapy for the trauma he endured as a child following the death of his mother – which gave him a newfound drive to become a family man

‘I don’t have the marriage chip, and neither of us have the greatest examples of marriages in our families,’ he told Parade. 

When it came to becoming a father, he seemed just as uninterested. He added: ‘I like kids but I also like the option to close the door.’ 

But now, it seems as though he is officially ready to become a married man. Us Weekly confirmed that he and Anna were engaged earlier this week, with a source telling the outlet that the proposal actually ‘happened a while back.’

‘They are still on cloud nine,’ the insider added. ‘They have so much fun together and already feel married.’

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