One of the most eligible bachelors in Hollywood, Jon Hamm, has changed his mind about getting married and announced that he is engaged to his companion, Anna Osceola.
During a courtship that began in 2020, Hamm, 52, and Osceola, 34, announced their intention to get engaged in February 2023. Even though the pair initially crossed paths in 2015 while shooting the last episode of the critically acclaimed television series “Mad Men,” they had no prior romantic ties to one another at the time. Hamm had been in a relationship with the actress and writer Jennifer Westfeldt for the previous 18 years before to beginning his connection with Osceola.
In an interview with Parade in 2010, Hamm stated that he did not have “the marriage chip,” and as a result, he had never really considered getting married. In addition to this, he said that he and Westfeldt did not have many models of healthy marriages to look up to while they were growing up.
Although stating that Westfeldt was the “love of (his) life,” the former couple, who met at a party in 1997, dissolved their long-term relationship in 2015. According to Entertainment Tonight, sources close to Hamm and Westfeldt indicated that she became bored of his “party-heavy lifestyle.” The breakup occurred when Hamm disclosed that he had checked himself into a rehabilitation facility to get treatment for his alcoholism.
Following his relationship with Westfeldt, Hamm was rumored to be dating actress Jenny Slate in 2017, after the two of them collaborated on the film “Aardvark.” The couple was seen out on dates around town and at Hollywood gatherings together, but their relationship didn’t last long and they broke up before it was even announced that they were dating.
After being seen together on a dinner date in New York, Hamm and Dakota Johnson, who stars in “Fifty Shades of Grey,” were rumored to be dating. On the other hand, nothing fruitful came out of the connection, and Johnson eventually moved on from Hamm and began dating Chris Martin of Coldplay.
Since May 2020, rumors of Hamm and Osceola’s possible romantic involvement have only become stronger. Dinner dates, tennis matches, and vacations to the beach were frequent activities for the couple to enjoy together.
Osceola was born in Cambridge, Massachusetts, but she went to Los Angeles to pursue a career in acting. Her first role was in the 2007 production of “Not Another High School Show.” In “On the television show “Mad Men,” she had a small part as a receptionist who greeted Jon Hamm’s character, Don Draper, when he arrived to a religious retreat facility.
After finishing production on the movie “Confess, Fletch” in 2021, Hamm and Osceola took a trip to Italy to relax and unwind. The fact that the couple does not have any social media accounts helps them keep their personal life out of the public spotlight, despite the fact that their images are routinely published in tabloids. When Hamm and Osceola attended an Oscars afterparty together in March 2022, it marked the beginning of the “red carpet” phase of their relationship. After that, the duo appeared at several events together that had a red carpet.
In the next year, September 2022, Hamm had an in-depth interview on the radio program of Howard Stern, where he discussed his shift in perspective towards marriage. He acknowledged that he was in a “good and comfortable” relationship with Osceola and realized that since he was in such a good headspace, he was ready to settle down because he is very much in love with Osceola. good and comfortable” relationship with Osceola and realized that since he was in such a good headspace, he was
When asked to describe his present relationship, Hamm described it as “a sensation of taking care of someone else and being taken care of at the same time.”
The actor also revealed that focusing on his mental health made all the difference in the world since it allowed him to “define a new version of happiness, life, and wellbeing” and opened his eyes to the “possibility of things like getting married, having kids.” He admitted that Osceola was responsible for a significant portion of this transformation, and she was the one who assisted him in processing the traumatic experience of losing his mother when he was 10 years old.