Jon Hamm's Ex Jennifer Westfeldt Has Been Doing Better Than Ever Since Their Split

Jon Hamm made headlines for being a long-time bachelor before settling down with fellow actor Anna Osceola in 2023. Once the former "Mad Men" co-stars announced that they're expecting their first child in 2026, some people brought up Hamm never getting married to his ex-girlfriend Jennifer Westfeldt. He dated actor and director Westfeldt for 18 years before they parted ways in 2015. Shortly after the two announced their split, an inside source told People that Westfeldt was acting like Hamm's mother, not his partner. "He has always had demons and needed a mother figure in his life," they said. "It was generally assumed that they would break up once he got sober, because he didn't need to lean on her to take care of him so much."

Spending almost 20 years with someone and breaking up truly isn't easy, but Westfeldt seems to be thriving in the aftermath. She wrote some episodes of "The First Lady," starring Viola Davis, Michelle Pfeiffer, and Gillian Anderson. She also wrote the screenplay for "The Idea of You," starring Anne Hathaway, and executive produced the 2024 film. As seen in the photo above from the movie's premiere, she was absolutely glowing.

The same year "The Idea of You" released, Westfeldt was set to adapt a novel called "The Sweet Spot" and star in the Amazon MGM Studios production. As of writing, it's unclear if that project is still in development. However, Westfeldt is a stage actor too and has kept busy with that. In 2025, for instance, Westfeldt co-starred in the play "The Assembled Parties" on the West End. The multi-hyphenate Hollywood creative has also gone out to star-studded events, like the 2022 Tribeca Film Festival.

While the public wants to focus on why the "Landman" star Jon Hamm never married Jennifer Westfeldt, she's seemingly more concerned with building her own success. Westfeldt doesn't often give interviews and doesn't have social media to update her fans, but her work is great enough to land a headline. After writing, producing, starring in, and sometimes directing indie romcoms for over a decade, Westfeldt co-wrote "The Idea of You" with the film's director Michael Showalter (based on the novel by Robinne Lee). The 2024 age-gap romance movie, starring Anne Hathaway and Nicholas Galitzine (who may be familiar from his other romance movie roles), gained 50 million views in the first two weeks after its Prime Video debut (via Variety).

Chris Ottinger, head of worldwide distribution at Amazon MGM Studios, told The Hollywood Reporter in 2024 that the success of "The Idea of You" inspired the company to continue appealing to female audiences. That same year, former Head of Amazon MGM Studios Jennifer Salke also told Variety that the film might have a sequel. Although there are no updates on the fate of the possible sequel as of writing, it's pretty iconic that Westfeldt's work seemingly sparked a wave of Amazon projects with strong female leads, especially because championing women in the arts is something important to her. In a 2022 interview on "Little Known Facts with Ilana Levine," Westfeldt said, "For one thing, if there's any thread to my career ... I've tried very hard to focus on female-driven stories and female creators, and write and create roles for women of all ages."