HomeEntertainmentJon Hamm and Anna Osceola are Reportedly Engaged After 2 Years of...

Jon Hamm and Anna Osceola are Reportedly Engaged After 2 Years of Dating

Jon Hamm and Anna Osceola are reportedly engaged! According to a report by People magazine, the Confess, Fletch co-stars are all set to walk down the aisle after almost 2 years of dating.

The two of them met each other for the first time on the set of the AMC series Mad Men in the year 2015. Read on to know more about the love story of Jon Hamm and his ladylove Anna Osceola.

Jon Hamm and Anna Osceola are reportedly engaged

It has been reported by the media outlet People magazine, that the Top Gun: Maverick star and the Law & Order: Special Victims Unit actress are engaged after nearly 2 years of dating. We are happy for the couple.

The lovebirds crossed paths on the set of the AMC series Mad Men in 2015. Anna had a small role in the final episode of the show. She played the role of a receptionist at Esalen, a spiritual California retreat that Hamm’s character, Don Draper, attended.

They were romantically linked to each other in the year 2020. At that time, they were spotted out and about in public on several occasions. They have even made a few red carpet appearances.

As of this moment, neither Jon Hamm nor Anna Osceola has made an official comment on the engagement reports swirling in the air. Hopefully, they will confirm the same in the times to come.

Jon Hamm opened up on his relationship with Anna Osceola in September 2022

While making a September 2022 appearance on Howard Stern’s SiriusXM show, Jon spilled the beans on his relationship with Anna Osceola. At that time, he disclosed he could see himself being married some day.

The Keeping Up With Joneses actor said, “This is all part of what I’m saying. This is another place in my life that I feel very settled and comfortable. I’m in a relationship right now and it’s comfortable.”

Hamm further added that he’s been able to sit down to start “really thinking about all that stuff, that’s made the relationship that I’m in now even more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness.”

Before confirming that he is “very much so” in love, Jon said, “It sounds hokey and whatever, but it’s real and for one of a better word, it’s what I’m working for. What else is there other than that?”

Anna Osceola is an actress

Just like Jon Hamm, his fiancée Anna Osceola is no stranger to the world of limelight. She is an actress by profession. She was born on April 8, 1988, in Cambridge, Massachusetts, which means she is 34 years old. Later on, she shifted to California to pursue a career in acting.

Anna made her acting debut in the year 2007 when she starred in the television movie Not Another High School Show as the character Charlie. Throughout the course of her career, she has made a few appearances on popular shows, including a three-episode arc on Greek, as well as roles on Rizzoli & Isles, NCIS, Law & Order: Special Victims Unit and Law & Order True Crime.

Is Anna Osceola active on social media?

The answer to the above question is a big no. Both Jon and Anna stay away from the world of social media. The couple has kept their personal lives including their relationships, private and away from the flashing cameras.

During a 2017 interview with InStyle, the Baby Driver actor talked about his decision to set boundaries in the industry and retain his own sense of self. Then, he said, “The point of life is not to put dog ears on yourself and post it online for everyone to see.”

Hamm went on to say, “It’s fun, it’s adorable, but it’s the visual equivalent of masturbating—there’s no point other than immediate gratification.”

Jon Hamm and Anna Osceola made their red carpet debut in March 2022

In March 2022, Jon and Anna took a big step in their relationship, when they decided to make their romance red carpet official at an Oscars afterparty. At that point in time, the couple marked their presence at the annual viewing party hosted by Mercedes-Benz, where Hamm is an ambassador.

This marked the first public outing of the pair together after nearly two years of dating. Soon after Hamm and Osceola also attended the Vanity Fair Oscars afterparty. Since then, the two of them have been clicked by paps many times like on the red carpet for the Sarah Silverman musical Bedwetter in New York City in May, at the 2022 ESPY Awards in July, and at a screening for Confess, Fletch in September.

Jon Hamm and Anna Osceola recently starred in the film ‘Confess, Fletch’ together

Yeah, you read that right. Jon and Anna joined hands for the third installment of the Fletch series. In the movie Confess Fletch, Hamm played the role of the semi-retired journalist Irwin M. Fletcher (originally played by Chevy Chase in 1985 and 1989).

On the other hand, when we talk about Anna’s character, she essayed the character of Larry in the movie. The film also stars Lorenza Izzo, Marcia Gay Harden, Kyle MacLachlan,  Roy Wood Jr., and John Slattery.

Jon Hamm was previously linked to Jennifer Westfeldt

Before sparking romance rumors with Anna Osceola, Jon Hamm was in a long-term relationship with actress Jennifer Westfeldt. The former couple pulled the plug on their romance in 2015 after a total of 18 years together.

At that time, the exes issued a joint statement to share the news of their split. The statement read, “With great sadness, we have decided to separate, after 18 years of love and shared history.”

It further read, “We will continue to be supportive of each other in every way possible moving forward.” Maybe Jon and Jennifer were meant to be just not meant to last.

Do you think Jon Hamm and Anna Osceola are a good match for each other? Kindly let us know your thoughts in the comments section below. Don’t forget to stay tuned with us for the latest updates from the world of showbiz.

Meenal Mehta
Hi, I am Meenal. I'm a travel enthusiast, a movie buff and a cricket fan all wrapped in one. I love to capture moments through my words. Writing is my happy space, it has been a great way of putting all my thoughts out and feel liberated.


Please enter your comment!
Please enter your name here

Most Popular