Photo: Kathy Hutchins, DFree, Featureflash Photo Agency/Shutterstock.com
He's now engaged to a new partner.
By John Sundholm — Written on Feb 28, 2023
Ask anyone who's had an intense experience with it—therapy changes everything.
And for actor Jon Hamm, 51, it was enough to fundamentally change his feelings about one of life's most funadmental issues—marriage.
After years of bachelorhood and a very long relationship during which he swore off the institution, the "Top Gun: Maverick" star seems to have made a 180 on it all recently.
And he credits his post-sobriety work in therapy with changing everything when it comes to matrimony.
Jon Hamm is engaged to fellow 'Mad Men' actor Anna Osceola.
Hamm and Osceola met while working together during the final season of "Mad Men," when Osceola played a receptionist at the Esalen-like retreat center Hamm's character Don Draper attends in the show's finale.
They were spotted out together several times in 2020 and were confirmed to be dating following an outing playing tennis in Los Angeles in May of that year.
Hamm and Osceola made their partnership official at the 2022 Oscars.
Hamm and Osceola were first spotted at an Oscars after-party in March 2022, where they made their red carpet debut as a couple.
The two went on to star together later in 2022 in "Confess, Fletch," the third installment of the "Fletch" series that starred Chevy Chase in the 1980s.
Hamm was previously linked to Jennifer Aniston after his guest appearance on "The Morning Show," but that definitely seems to have been false.
Hamm and Osceola's engagement was announced earlier this week but Hamm popped the question some time ago, according to anonymous sources.
"The engagement happened a while back, but they are still on cloud nine," someone claiming to be close to the couple told US Weekly. "They have so much fun together and already feel married."
Hamm was previously in a relationship with actor and writer Jennifer Westfeldt for 18 years, and said he never wanted to get married or have kids.
Hamm and Westfeldt began dating in 1997, before either were public figures, and he famously had a pre-fame cameo in Westfeldt's first film, "Kissing Jessica Stein," in 2001.
Westfeldt went on to work regularly as an actress, writer and filmmaker while Hamm worked toward his big break in "Mad Men," which began in 2007.
The two were one of those rare couples whose relationship held strong even after Hamm rocketed to A-list stardom. But despite that sturdy foundation, Hamm repeatedly said marriage and kids were off the table.
In a 2010 interview with Parade magazine, Hamm said neither he nor Westfeldt were much interested in marriage.
"I don't have the marriage chip, and neither of us have the greatest examples of marriages in our families," he told the magazine.
Hamm took a similarly dim view of fatherhood. "I like kids but I also like the option to close the door," he said.
Hamm reiterated his lack of interest in having kids in an interview with US Weekly in 2012, while he and Westfeldt were working on her film "Friends With Kids."
"I'd be a terrible father!" he told US Weekly. "I see my friends who have children and I'm like, 'Dude, how are you even upright, much less here at work at 6 a.m.?'"
Hamm and Westfeldt split in September 2015, allegedly due to Hamm's problems with alcoholism.
Hamm entered rehab for alcohol addiction in 2015, just before filming began for "Mad Men's" final season, with Westfeldt full support.
But by September, the couple split, and Hamm's "party-heavy lifestyle" was allegedly to blame, as seen in the video below.
A source claimed Westfeldt was also "tired of being his mother" and "wanted him to grow up, but he didn't want to."
Hamm has credited addressing childhood trauma in therapy for changing his perspective on marriage and making his relationship with Osceola work.
The most famous takeaway from Hamm's 2022 interview with Howard Stern focused on the infamous, uh, bulge in his pants that often seems to show up in his paparazzi photos.
But as seen in the video below, after some playful ribbing about that whole thing, Stern and Hamm got into some rather personal things.
Hamm told Stern that "working on my mental health" and addressing the trauma of losing his mother at the age of 10 made him able to consider marriage for the first time. —
"When you lose someone that’s so important to you, like a mother, so early," he told Stern, "that creates a wound that blocks a lot of that emotional accessibility."
And doing so changed not only his relationship with Osceola, but the rest of Hamm's life too.
"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."
Hamm went on to perfectly sum up the life-changing impact of therapy and mental wellness.
"All that stuff sounds hokey and whatever," he continued, "but it’s real and it’s — for want of a better word — it’s what I’m working for. What else is there other than that?”
John Sundholm is a news and entertainment writer who covers pop culture, social justice and human interest topics.