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Wedding Bells? ‘Top Gun: Maverick’ Star Jon Hamm Is Reportedly Engaged To Anna Osceola

According to reports, Jon Hamm and Anna Osceola recently got engaged after three years of dating.

The couple first met as co-stars while filming the final season of “Mad Men” in 2015 and managed to keep their budding romance out of the public eye until 2020, when they were photographed together several times.

In an interview with Howard Stern last September, Hamm professed his love, saying he was completely smitten by Osceola and could envision a future with her.

Read on to learn more.

Jon Hamm and Anna Osceola Set to Tie the Knot

Jon Hamm, Anna OsceolaMEGA

According to a report by People magazineJon Hamm and Anna Osceola are ready to take their relationship to the next level and recently got engaged after dating for three years.

In a classic case of on-set romance, Hamm, 51, and Osceola, 34, first met while filming the final season of “Mad Men,” which premiered in 2015.

They were photographed together once in 2017, but it wasn’t until early 2020 that they were spotted several times, sparking rumors of a budding romance.

Red Carpet Debut of Jon Hamm and Anna Osceola

Jon Hamm, Anna OsceolaMEGA

Despite their efforts to keep their relationship out of the public eye, the low-key lovebirds have been seen taking part in various activities together, including playing tennis in May and enjoying a relaxing day at the beach in Santa Barbara, California, in September.

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Although the “Confess, Fletch” co-stars kept a low profile about their relationship, the couple flaunted their love while enjoying their Italian vacation in September 2021. Their bond grew stronger over time, leading to their reported engagement.

In March 2022, the couple took an important step in their relationship by appearing publicly together on the red carpet. The “Top Gun: Maverick” actor and “Law & Order True Crime” actor made their red carpet debut at the Mercedes-Benz Academy Awards viewing party and later attended Vanity Fair’s exclusive annual event.

‘It’s Nice And Comfortable’

Jon Hamm, Anna OsceolaMEGA

During an interview with Howard Stern last September, Hamm didn’t hold back when discussing his feelings for his partner, Osceola. She revealed that she is “absolutely” in love with the actor and could easily see herself spending the rest of her life with him.

Hamm described their relationship as cozy and nurturing, stating, “It’s nice and cozy, and it feels like caring for someone else and being cared for.” According to him, Osceola has opened up new possibilities, such as the prospect of marriage, having children, and defining a new version of happiness and well-being in his life.

It’s clear that Hamm’s love for Osceola is deep and genuine, and he’s excited about the future they might share.

Jon Hamm Credits Anna Osceola For Her Growth Journey

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In a revealing conversation, Hamm also opened up about the transformative impact his relationship with Osceola had on his life. He stated that his feelings for her were sincere, and that he could not imagine anything more satisfying than spending his life with her.

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Hamm admits that others may consider his sentiments trite but insists that they are genuine and reflect his true desires.

follow Page Six, he went on to explain that his devotion to Osceola was his priority, and nothing meant more than cultivating a strong and loving relationship with her. He stated, “All that stuff sounds hokey and whatever, but it’s real. And, for want of a better word, that’s what I’m working on. What else is there?”

GQ Men's Best 2019 - ArrivalsMEGA

In addition to the joy that Osceola brought to his life, Hamm also credits him for being a part of his growth journey. He shared that she helped him cope with and process the lingering emotional pain of losing his mother when he was just ten years old.

Before rising to fame in the hit movie “Baby Driver,” the talented actor was previously in a committed romantic relationship with fellow actress and screenwriter Jennifer Westfeldt for nearly two decades, spanning from 1997 to 2015.

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