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.”