Who Is Jon Hamm's Girlfriend Anna Osceola, And How Did They Meet?
Once someone is a star, it becomes extremely difficult for them to go out in public without being surrounded by a mass of fans. As a result, it makes sense that a lot of famous people wind up dating other celebrities, especially when the star in question is incredibly good-looking.
Unlike a lot of his peers, Jon Hamm has managed to stay out of the tabloids for the most part throughout his time in the public eye. One of the main reasons for that is Hamm has never dated another massive star. With that in mind, it begs an obvious question, who is Jon Hamm’s rumored girlfriend, Anna Osceola?
Putting Together An Enviable Career
Even though Jon Hamm seems to have been born to be a star, he spent many years banging around Hollywood before he caught his big break. Fortunately for Hamm and his legions of fans, everything changed for the actor once he landed the starring role in TV’s Mad Men. Turned into a massive star pretty much overnight, Hamm portrayed Mad Men’s Don Draper from 2007 until 2015.
Unlike some TV stars whose careers hit the skids once their famous show ends, Jon Hamm didn’t seem to miss a beat. Instead, Hamm has worked so much since Mad Men came to an end that it can be hard to keep track of him at times. For example, Hamm headlined films like Minions, Baby Driver, Bad Times at the El Royale and he is set to appear in the upcoming films Top Gun: Maverick. On top of all those credits, Hamm appeared in shows like Unbreakable Kimmy Schmidt, Legion, Good Omens, and Bless the Harts among others.
Jon’s New Love
Unlike some stars who appear to document every moment of their lives to let the world in on every detail of their life, Jon Hamm is a pretty private guy. For example, there is no way to know for 100% sure that Hamm is dating Anna Osceola as he has never confirmed or denied their relationship status. However, multiple sources familiar with the pair have confirmed that they are a couple and they’ve been caught on camera multiple times so it seems safe to take those reports at face value.
Cast as a character who shared a scene with Jon Hamm’s Don Draper during the finale episode of Mad Men, Anna Osceola clearly caught the actor’s eye when they met on set. However, Hamm was with another woman at the time and based on all reports, it seems clear that Osceola and Hamm only became friendly at that time. Said to have remained casual friends in the years that followed, Osceola and Hamm reportedly became a couple several months after Jon and his past longtime girlfriend split.
Long before Anna Osceola and Jon Hamm met, she was born in Cambridge, Massachusetts, and became the face of Abercrombie & Fitch for a while. Able to find some success as an actor, Osceola has landed roles in several TV shows. For example, on top of Osceola’s Mad Men role, she portrayed recurring characters in the shows Greek and Law & Order True Crime and she popped up in other series like Rizzoli & Isles and NCIS.
Jon’s Past Relationship
Roughly a decade before Mad Men turned Jon Hamm into a worldwide star, he began dating Jennifer Westfeldt. An extremely talented person, Westfeldt co-wrote and co-produced the criminally underrated romantic comedy Kissing Jessica Stein. On top of that role, Westfeldt starred in other movies like How to Lose Your Lover, Keep Your Distance, and Friends with Kids in which she co-starred with Hamm. On the television front, Westfeldt landed roles in a lot of popular shows including Judging Amy, Numb3rs, Private Practice, Grey's Anatomy, 24, and Girls.
After dating from 1997 until 2015, Jon Hamm and Jennifer Westfeldt announced their relationship was ending in a statement. "With great sadness, we have decided to separate, after 18 years of love and shared history," the statement read. "We will continue to be supportive of each other in every way possible moving forward." Considering how long Westfeldt and Hamm were together, it shouldn’t come as a surprise to anyone that Jon has said that it was very painful to split up with Jennifer. In fact, during a 2017 InStyle interview, Hamm spoke about how hard it was for him to accept the fact that he was single at that time.
Asked about how fun it is to be single considering that he was “a perennial on those sexiest-man-alive lists”, Hamm is said to have looked down before saying “it’s fine”. After that surface-level answer, Hamm seemingly let the interviewer in on how he truly felt about the situation. “It’s hard. It’s hard to be single after being together for a long time. It’s really hard. It sucks.”
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