Jon Hamm Met Wife Anna Osceola on the Set of "Mad Men"

Published on 9/6/2023 at 4:40 PM

Jon Hamm and Jennifer Westfeldt had been together for 18 years when they announced their separation in September 2015. After their split, the "Mad Men" star remained single for a few years before he began dating again. In June 2017, Hamm told InStyle that being alone was "really hard," however, he needed the space in order to focus on his mental health. "Medical attention is medical attention whether it's for your elbow or for your teeth or for your brain," Hamm said at the time.

The actor's years in therapy proved to be a life-changing experience. During an interview on "The Howard Stern Show" in September 2022, Hamm revealed therapy led him to become more emotionally available after being able to "unpack" the trauma of losing his mother at a young age. "It's been a process of working on myself," he said. So when Hamm began dating actor Anna Osceola in 2020, he said, he began opening himself up to the possibility of marriage and kids. "It's only been in the last couple of years, me kind of sitting down and really thinking about all that stuff that's made the relationship that I'm in now even more meaningful," Hamm told Stern.

Hamm and Osceola tied the knot on June 24, 2023. Since the couple keep things low-key, you might be wondering how they first met. As it turns out, "Mad Men" brought them together.

Check out Hamm's dating history ahead.

Jennifer Westfeldt

Hamm was in a long-term relationship with Westfeldt from 1997 to 2015. Their 18-year relationship began during the 1990s when they were both just beginning their acting careers. In an October 2011 interview with The Hollywood Reporter, Hamm opened up about how they first connected. "Jen and I met in LA at a party — a mutual friend's birthday party," he recalled.

The pair later reunited when Westfeldt asked Hamm for a favor. "She got an audition for Jake Kasdan's film 'Zero Effect' and wanted to read with somebody who was a guy, and she didn't really know any guys out here, so she called," Hamm said. "That was, kind of, how we first officially met, running scenes from 'Zero Effect.' Apparently, I wasn't very good, 'cause she didn't get the part."

While talking to The Guardian in June 2012, Westfeldt admitted that she initially wasn't interested in Hamm because she got the impression he was "an arrogant guy." However, when he didn't hesitate to help Westfeldt with her audition, she began to see him in a new light. "Jon was so sweet and he worked on these lines with me. I was like, 'God, this guy is so talented . . . and so handsome!'" Despite her attraction to Hamm, Westfeldt didn't date the actor right away since they were both in other relationships at the time. "She was involved with somebody, and I may have been involved, as well," Hamm told The Hollywood Reporter in 2011. "Yeah, we were friends for a long time before we officially started dating — and we've never gotten out of the 'dating' thing. We're still in it."

Over the years, Hamm and Westfeldt became known as a power couple in Hollywood. In April 2009, they launched a production company called Points West Pictures. As part of their new collaboration, the pair worked together on the film "Friends With Kids," in which Hamm starred and Westfeldt wrote, produced, and directed.

After being together for nearly two decades, Hamm and Westfeldt announced their breakup in September 2015. "With great sadness, we have decided to separate, after 18 years of love and shared history. We will continue to be supportive of each other in every way possible moving forward," the stars said at the time, according to Entertainment Tonight. A source reportedly told the publication the actors "fought hard" for their relationship, but it ultimately proved to be "too much work."

Lindsay Shookus

Hamm was also romantically linked to TV producer Lindsay Shookus, who's known for her work on "Saturday Night Live." In September 2019, the stars were seen attending the Broadway premiere of "Derren Brown: Secret." A source told People that the pair looked like "they were on a date."

"They sat together on the aisle and looked like they were having a great time," the source said. "Both raved about the show at intermission, too." Hamm and Shookus appeared to enjoy each other's company as "they locked eyes and were smiling the whole time" while talking. Apparently, they decided to go on a date after knowing each other for years.

Hamm and Shookus seemingly went on another date that November after Hamm appeared on "Saturday Night Live." According to Us Weekly, the pair attended an "SNL" afterparty and had dinner together. "They sat next to each other and would touch each other affectionally throughout the night. However, there was no PDA," a source said.

Their relationship didn't appear to be serious, as the stars weren't seen together again.

Anna Osceola

"Mad Men" introduced Hamm to his now-wife. Osceola appeared in the final episode of the hit series as Clementine, a receptionist Hamm's character comes across during a retreat. Although it's unclear when Hamm and Osceola began dating, they were first spotted out in public in 2017. That January, the stars were seen leaving a coffee shop together in Los Feliz, CA, per photos published by Just Jared.

In March 2019, the pair were also photographed having dinner in Hollywood, as seen in photos obtained by Daily Mail. And a year later, Hamm and Osceola reunited again for a tennis date in May 2020, and Us Weekly confirmed that June that the former costars were an item.

Hamm and Osceola went public with their relationship by making their red carpet debut together at an Oscars viewing party in March 2022. That September, Hamm teased his relationship with Osceola was getting serious. While appearing on "The Howard Stern Show," the star said he feels very "settled" and "comfortable" with his girlfriend and was even thinking about the couple's long-term plans. "It opened up the possibility of being married, having kids, defining a new version of happiness, life, wellness. All that stuff, it sounds hokey and whatever, but it's real," he said. "It's what I'm working for." When Stern noted that Hamm looked like he was in love, the actor responded by saying, "I'm very much so. I am."

Stern said he saw wedding bells in their future, and he was right. On Feb. 27, 2023, People confirmed Hamm and Osceola were headed down the aisle. On June 24, 2023, the couple got married in Big Sur, CA.