Jon Hamm And Anna Osceola Are Reportedly Engaged After 3 Years Of Dating

After three years of dating, Jon Hamm and Anna Osceola are allegedly engaged. People confirmed the news Monday, though the actor’s rep did not immediately respond to Page Six’s request for comment.

The “Confess, Fletch” During the production of the series finale of “Mad Men,” which premiered in 2015   Even though Hamm, 51, and Osceola, 34, were seen together just once in 2017, they didn’t start dating until the beginning of 2020, when they were frequently spotted out together.

The discreetly in love couple, who both avoid social media, were seen playing tennis together in May before spending a day at the beach in Santa Barbara, California, in September.

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Although they have kept their romance fairly quiet, the couple was seen engaging in intense PDA while on vacation in Italy in September 2021.

The “Top Gun: Maverick” actor and the “Law & Order True Crime”  actress and actor walked the red carpet for Mercedes-Academy Benz’s Awards viewing party in March 2022, which was followed by Vanity Fair’s annual afterparty.

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

Jon Hamm And Anna Osceola Are Reportedly Engaged
Jon Hamm And Anna Osceola Are Reportedly Engaged

“It’s good and comfortable, and it’s a 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.”

He 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?”


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Hamm also credited Osceola for being integral in the “process of working on [himself],” which included “unpacking” the trauma of losing his mom when he was 10 years old.

The “Baby Driver” Before, from 1997 until 2015, star was engaged to actress and screenwriter Jennifer WestfeldtThe exes announced their breakup in a joint statement, vowing to “continue to be supportive of each other in every way possible moving forward.”

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