How Jon Hamm Found Love in Anna Osceola after Ending his Long-Term Relationship with Jennifer Westfeldt!

Updated On March 18, 2024 | Published By: Natalie | In Couple , Dating , Engagement

Jon Hamm and Anna Osceola have been dating for years now. source: Page Six

Jon Hamm and Anna Osceola are engaged after three years of togetherness.
The actors initially met while filming the finale of Mad Men which premiered in 2015.
The lowkey couple loves to keep most of their love life out of the spotlight.

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Jon Hamm and Anna Osceola are reportedly engaged

Jon Hamm and Anna Osceola are allegedly engaged after dating for more than three years.

People confirmed the news on Monday. But the couple has still not officially announced the news themselves.

The actors who starred together in Confess, Fletch, initially met while filming the series finale of Mad Men which premiered in 2015.

Fans suspected that the couple started dating in 2017 as they were once photographed together. However, Jon, 51, and Osceola, 34, only seemingly confirmed their romance in 2020 when they were seen hanging out multiple times in early 2020.

Jon Hamm — The two met in 2017. source: Page Six

That year in May, the private couple who are both away from social media enjoyed playing tennis together. Four months later, they enjoyed a beach day in Santa Barbara, California.

Despite keeping their love life a secret, the Top Gun: Maverick star and the Law & Order True Crime actress showed some PDA during their intimate vacation in Italy in September 2021.

In 2022, the pair seemed comfortable showing their relationship in public. In March of that year, they made their red carpet debut as a couple at the Mercedes-Benz Academy Awards viewing party. Then came Vanity Fair’s annual afterparty.

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Jon was in a long-term relationship with actress Jennifer Westfeldt

Last September, Hamm opened up about his relationship with Osceola to Howard Stern. He said that he was very much in love with her. He added that he could see himself spending the rest of his life with her.

Jon said,

“It’s good and comfortable, and it’s a feeling about taking care of someone else and being taken care of,”

Jon also gushed about the actress opening up about the ‘‘possibility of things like being married, having kids, you know, defining a new version of happiness, life, wellness.”

The Baby Driver actor added,

“All that stuff sounds hokey and whatever, but it’s real. And, for want of a better word, it’s what I’m working for. What else is there other than that?”

Moreover, Hamm also credited his girlfriend for playing a massive role in the “process of working on [himself].” It included unpacking the pain of losing his mother when he was a young boy.

Before Anna, the actor was in a long-term relationship with actress and screenwriter Jennifer Westfeldt. The couple dated from 1997 to 2015.

The exes released a statement to announce their breakup and promised to “continue to be supportive of each other in every way possible moving forward.”

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