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Celebrity Couple Jon Hamm And Anna Osceola Announces Engagement After 3 Years of Dating

It‘s official: Actor Jon Hamm and actress Anna Osceola are engaged! After months of speculation, the couple has confirmed their commitment to each other with a joint statement released recently. The two have been together for a couple of years. Since then, they have enjoyed spending time together and getting to know one another.

Celebrity Couple Announces Engagement After 3 Years of Dating

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Ladies, Jon Hamm, is no longer available for marriage. Reportedly, the Mad Men actor is engaged to actress Anna Osceola. The couple has been together for the past three years. They were first introduced in Confess, Fletch, and Mad Men, where they co-starred—the final season of Mad Men premiered in 2015.

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Even though Hamm, 51, and Osceola, 34, were spotted together just once in 2017, they began dating at the beginning of 2020, when they were seen frequently. The couple, who both avoid social media, was spotted playing tennis together in May last year. In September, they were also spotted enjoying a day at the beach in Santa Barbara, California. In September 2021, despite keeping their relationship relatively private, the couple was observed engaging in intense PDA while on vacation in Italy.

Hamm told Howard Stern in September that he was “very much” in love with Osceola and that he “could definitely” see himself spending the rest of his life with her.

“It’s good and comfortable, and it’s feeling about taking care of someone else and being taken care of,” he gushed at the time, explaining that the actress had “opened up the possibility of things like being married, having kids, you know, defining a new version of happiness, life, wellness.”

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Jon Hamm &  Anna Osceola’s Romantic Journey

PEOPLE confirms that the Confess, Fletch co-stars are engaged after three years of dating. The pair reportedly met for the first time in 2015 on the sec series Mad Men set for the first time, before being spotted together on multiple occasions and being romantically linked in 2020. While Hamm and Osceola were photographed together in 2017, dating rumors did not surface until 2020, years later. Since then, they’ve been spotted a few times throughout their two-year relationship and have made a few red-carpet appearances, but they’ve kept most of their relationship’s details under wraps.

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In a rare interview with Howard Stern on his SiriusXM show on September 19, 2022, Hamm discussed his relationship with Osceola. Hamm responded, in response to Stern’s inquiry as to whether he would ever be able to get married, that he could see himself achieving this goal in the future.

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“This is all part of what I’m saying. I feel very settled and comfortable in this place in my life. I’m in a relationship right now, and it’s comfortable,” he said, explaining that he’s been working on himself and his mental health with a therapist.

In March 2022, Hamm and Osceola took a significant step in their relationship by making their red carpet debut at an Oscars afterparty. The couple attended the Mercedes-Benz annual viewing party and an appearance at the Vanity Fair Oscars afterparty. Since then, they have appeared together on the red carpet for the Sarah Silverman musical Bedwetter in New York City in May, at the 2022 ESPY Awards in July, and at a screening of Confess, Fletch in September.

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Know More About Fiancée of Jon Hamm?

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Since 2020, Jon Hamm has been dating Anna Osceola. She is a 35-year-old Cambridge, Massachusetts-born actress. Her birthday is April 8, 1988. The age difference between the couple is 17 years. Osceola has an acting resume, with her big break coming in 2007 with the television film Not Another High School Show. She has also appeared on Greek, Rizzoli & Isles, and Law & Order: True Crime, among other programs. She additionally appeared in The Menendez Murders.

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Who Did Jon Hamm Date Before Anna Osceola?

Before dating Osceola, Hamm dated actress Jennifer Westfeldt for eighteen years. From 1997 until 2015, they were an item. “We will continue to support each other in every way possible in the future,” they said in a joint statement.

Actors Jon Hamm ) and Jennifer Westfeldt attend the PEOPLE Magazine Awards at The Beverly Hilton Hotel | Image

Before their breakup, Hamm had completed alcohol rehabilitation and credited Westfeldt for her support during this time. The ex-couple co-starred in the 2011 film Friends with Children. As collaborators, they also produced A Young Doctor’s Notebook, an original Netflix limited series.

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Before dating Osceola, Hamm dated several stunning women. In 2017, he was rumored to be dating his Aardvark co-star Jenny Slate after the two were seen leaving a movie theatre hand-in-hand. He was also believed to have dated actress Dakota Johnson in the same year. In 2017 and again, rumors circulated that Hamm dated Saturday Night Live producer Lindsay Shookus

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