At 52, Jon Hamm Is Ready To Settle Down With Fiancée Anna Osceola After Changing His Stance On Marriage

Mar 10, 2023 by apost team

Jon Hamm, one of Hollywood's most eligible bachelors, changed his mind about getting married and got engaged to partner Anna Osceola.

After dating since 2020, Hamm, 52, and Osceola, 34, confirmed their engagement in February 2023. Though the couple first met while filming the final episode of the award-winning TV series "Mad Men" in 2015, they were not romantically linked at that time. Before dating Osceola, Hamm was in an 18-year relationship with actress and writer Jennifer Westfeldt. 

In 2010, Hamm admitted in an interview with Parade that he was missing "the marriage chip" thus he never thought of getting married. He also said that he and Westfeldt didn't have a lot of good marriages to look up to growing up.  

Despite declaring that Westfeldt was the "love of (his) life," the former couple, who met at a party in 1997, ended their long-term relationship in 2015. Sources close to Hamm and Westfeldt said that she grew tired of his "party-heavy lifestyle," according to Entertainment Tonight. The split came after Hamm revealed that he went into rehab to deal with his alcohol addiction.

After Westfeldt, Hamm was linked to actress Jenny Slate in 2017 after they worked together in the movie "Aardvark." The pair was seen about town on dates and attended Hollywood functions together but their romance was short-lived and ended even before it was confirmed.

Hamm was also linked to "Fifty Shades" star Dakota Johnson after the two were spotted on a dinner date in New York. However, nothing blossomed out of that relationship and Johnson moved on from Hamm to Coldplay's Chris Martin.

Since May 2020, whispers about Hamm and Osceola together have only gotten louder. The pair often stepped out for dinner dates, tennis games and trips to the beach. 

Born in Cambridge, Massachusetts, Osceola moved to Los Angeles to pursue acting and made her debut in "Not Another High School Show" in 2007. On "Mad Men,” she had a small role as a receptionist who welcomed Hamm's Don Draper to a spiritual retreat center. 

In 2021, Hamm and Osceola enjoyed an Italian vacation after filming the movie "Confess, Fletch." Despite their photographs appearing frequently in tabloids, the couple has managed to keep their lives out of the public eye as the pair are not on social media. In March 2022, Hamm and Osceola made their relationship red-carpet official when they attended an Oscars afterparty. The pair subsequently attended more red-carpet events together.

Hamm then opened up about his changed stance on marriage in an in-depth interview on Howard Stern's radio show in September 2022. He admitted to being in a "good and comfortable” relationship with Osceola and realized that since he was in such a good headspace, he was ready to settle down because he is very much in love.

"It’s a feeling of taking care of someone else and being taken care of," Hamm said, describing his current relationship. 

The actor also admitted that working on his mental health made all the difference as it opened his eyes to the "possibility of things like being married, having kids, defining a new version of happiness, life, wellness." He acknowledged that a huge part of this change was Osceola, who also helped him unpack and understand the trauma of losing his mother at 10 years old.

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Is it too late for a man to change his mind about marriage? What do you think of how Jon Hamm sees his future with his fiancée? Let us know your thoughts and pass this story along for inspiration!