Jon Hamm, who played the renowned yet mysterious Don Draper in Mad Men, appears in Top Gun: Maverick as Beau “Cyclone” Simpson, the current head of the Top Gun flight school and a skeptic of Tom Cruise’s Pete “Maverick” Mitchell. While his romantic heroes and leading men onscreen have their own confident swagger, his personal life is far more low-key.
It’s difficult in Hollywood to keep romances secret, but Hamm and his girlfriend Anna Osceola have done just that by avoiding social media and maintaining their relationship confidential. “The objective of life isn’t to put dog ears on oneself and upload it to the internet for everyone to see,” he explains. “It’s pleasant, it’s beautiful, but it’s the visual equivalent of masturbation—no there’s a reason other than quick fulfillment,” he said of being in a social media-free zone to InStyle.Having said that, Hamm is head over heels in love with his new lady. He informed Howard Stern in a September 2022 interview that he is “very much” in love with Osceola.
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“I’m in a relationship right now, and… it’s pleasant, it’s a feeling of caring for someone else and being cared for,” he explained. Hamm noted that being open to the prospect of getting married takes effort, particularly coming to grips with the loss of his mother when he was 10 years old.”Working on myself, my mental health, and everything else with my therapist has also been a process. And unraveling all of that pain and realizing that losing someone so significant to you, like a mother, so young creates a wound that prevents a lot of that emotional accessibility, “Hamm stated. “A lot of that accessibility and susceptibility is blocked by that.”
“I only kind of sat down and actually thought about all that material in the last couple of years,” he continued, “which has made the relationship I’m in now even more significant and brought up the potential of things like being married, having kids, and creating a new version of pleasure, life, and wellbeing. “It sounds cheesy and whatever, but it’s real and it’s what I’m working towards, for lack of a better word.”Here is what is known about the relationship between Jon Hamm and his girlfriend Anna Osceola, despite the fact that they are very secretive.
Girlfriend of Jon Hamm
“Jon Hamm and Anna Osceola have been dating since 2020. She is a 34-year-old Cambridge, Massachusetts-based actor. On April 8, 1988, she was born. The couple has a 17-year age difference. Osceola has a long number of acting credits, including a role in the 2007 television film Not Another High School Show. She’s also appeared on Greek, Rizzoli & Isles, and Law & Order: True Crime. She was also in The Menendez Murders.
How did Jon Hamm and Anna Osceola meet?
On the set of Mad Men in 2015, where Osceola was portraying the receptionist at the retreat that Hamm’s character Don Draper went to in the season finale, the pair truly got together. They did not, however, fall in love until years later. Since then, their relationship has remained primarily secret, with only a few public appearances. From Super Bowl Sunday festivities to an Italian vacation in September 2021, the couple has been seen spending quality time together.
The two met during the annual Mercedes-Benz party, to which Hamm serves as an ambassador. This was the couple’s first public appearance together, and it provides assurance that they are indeed in a relationship. They were most recently seen posing on the red carpet at the Top Gun: Maverick premiere.
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Rumors about Hamm’s relationship with Osceola have circulated for years. In 2018, the two were photographed playing tennis together, but in 2017, they were observed leaving a coffee shop.
Jon Hamm Dating History
Hamm had an 18-year marriage to the actress Jennifer Westfeldt before he started dating Osceola. They were together from 1997 until their divorce in 2015. “We will continue to be supportive of each other in any manner possible moving ahead,” they declared at the time in a joint statement.
Prior to their breakup, Hamm had finished alcohol recovery, and he acknowledged Westfeldt for her support during the process. The ex-couple co-starred in the 2011 film Friends with Kids. They also collaborated on the Netflix original limited series A Young Doctor’s Notebook.
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Prior to meeting Osceola, Hamm was associated with a number of lovely ladies. After the couple was seen leaving a movie theatre holding hands in 2017, it was speculated that he was dating his Aardvark co-star Jenny Slate. That same year, he was said to be dating actress Dakota Johnson. Rumors circulated in 2017 and 2019 that Hamm dated Saturday Night Live producer Lindsay Shookus.
