Jon Hamm & Anna Osceola Are Married 8 Years After Meeting On The Set Of Mad Men

They reportedly tied the knot in front of several famous faces.

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BEVERLY HILLS, CALIFORNIA - MARCH 12: Anna Osceola, Jon Hamm attend the 2023 Vanity Fair Oscar Party...
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Jon Hamm is off the market. After reportedly proposing to his Confess, Fletch co-star Anna Osceola in February, after two years of dating, the Mad Men actor is now married, People confirmed on June 25. Hamm and Osceola met in 2015 on the set of Mad Men while filming the AMC series’ final season. At the time, Hamm had called it quits in September 2015 with Jennifer Westfeldt after 18 years together.

Meanwhile, Massachusetts native Osceola appeared on NCIS and In Plain Sight, slowly adding television roles to her resume. Reports of them dating surfaced in 2017, but they escalated when the couple was photographed out and about in 2020. Both actors are off social media and notoriously private, but they’ve made several red-carpet appearances together throughout their relationship. Their first outing since Hamm popped the question was a star-studded one — the 2023 Oscars.

Here’s what we know about their relationship, from meeting to their engagement.

2015: Meeting On Mad Men

Jon Hamm in 2015.Dave Kotinsky/Getty Images Entertainment/Getty Images

Osceola had a minor role in “Person To Person,” one of the series’ final episodes as a receptionist named Clementine at a retreat Hamm’s Don Draper checks into. Hamm and Westfeldt also broke up the same year after dating since 1997. They announced their breakup in a joint statement, promising they would “continue to be supportive of each other in every way possible moving forward.”

2020: Rumors Of A Relationship

The actors were rumored to be dating in 2020 when they were photographed together at a beach in Santa Barbara, Calif. A source told PEOPLE at the time that “they looked very happy together. They definitely seem to be dating.” Though they had been spotted together before in 2017, this outing appeared to ignite further speculation of a relationship.

March 2022: Red Carpet Debut

Jon Hamm and Anna Osceola in 2022.Arturo Holmes/FilmMagic/Getty Images

Hamm and Osceola made things official with their red carpet debut at the 2022 Academy Awards, attending the Vanity Fair Oscar Party. They also stopped by the Mercedes-Benz’s Academy Awards afterparty that night, per Page Six.

September 2022: Hamm Opens Up About Marriage

Hamm and Osceola kept their relationship private, and only in September 2022 did Hamm open up about it. “This is all part of what I’m saying. 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 said during an appearance,” he told Howard Stern. He also said he was feeling more open to “the possibility of things like being married, having kids, defining a new version of happiness, life, wellness.”

“It sounds hokey and whatever, but it’s real and for one of a better word, it’s what I’m working for,” Hamm added. “What else is there other than that?”

September 2022: Confess, Fletch Premieres

Robin L Marshall/Getty Images Entertainment/Getty Images

Hamm and Osceola reunited on screen in 2022 when Confess, Fletch premiered. The movie, which was shot in 2021, served as a mini Mad Men reunion, as John Slattery (Roger Sterling) also appeared in the film.

February 2023: They’re Engaged

Jon Hamm and Anna Osceola in May 2022.Emma McIntyre/WireImage/Getty Images

PEOPLE reported on Feb. 27 that Hamm and Osceola are engaged. Hamm and Osceola have yet to comment publicly on the engagement.

March 2023: First Outing As An Engaged Couple

Jon Hamm and Anna Osceola in 2023.Lionel Hahn/Getty Images Entertainment/Getty Images

Hamm and Osceola marked their first outing as an engaged couple at the 2023 Academy Awards. The pair, donned in black-and-white ensembles and big smiles, attended the 2023 Vanity Fair Oscar Party. Osceola also showed off her engagement ring. PEOPLE reports that her ring features an emerald-cut solitaire diamond.

June 2023: Wedding Bells

Jon Hamm and Anna Osceola in 2023.Theo Wargo/Getty Images Entertainment/Getty Images

TMZ first reported that Hamm and Osceola were married on June 24 at Anderson Canyon in Big Sur — also the location of the Mad Men series finale. Though reps for the couple would not comment on the reported marriage, the website posted photos from the ceremony, and People confirmed the news soon afterward. According to TMZ, Slattery, Paul Rudd, Tina Fey, and Billy Crudup were among their famous friends who attended the wedding, which included the James Bond You Only Live Twice theme as a walkup song.

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