According to Us Weekly, the longtime couple broke up because they had different views on starting a family. Though they reportedly “definitely tried” to make things work, Hamm, 44, and Westfeldt, 45, ultimately parted ways because they couldn’t agree on children.
“There’s always been a rift,” a source said. “Because he wanted kids and she didn’t.”
In 2012, Westfeldt spoke about her decision to not have children, telling the New York Times, “I never thought I’d be this age and not have kids. But my life has also gone in a million ways I never anticipated.”
She explained, “I kept feeling like I’d wake up with absolute clarity, and I haven’t. And we have a pretty great life together. The chance that we’ll regret it doesn’t seem like a compelling enough reason to do it. I may wake up tomorrow with that lighting bolt, and I’ll have to scramble to make it happen. You were wondering how we make it work. One way is we’re really mobile. No one’s had to give up an opportunity they really wanted.”
The two, who started dating in 1997 and starred alongside one another in 2011’s Friends With Kids, also chose not to marry because they were both children of divorce.
“Neither of us have the greatest examples of marriages in our families,” Hamm told Parade in 2010. “But Jen is the love of my life, and we’ve already been together four times longer than my parents were married.”
“I like kids but I also like the option to close the door,” he also said in the same interview. “Becoming a parent is a whole other life, and it doesn’t stop.”
According to Entertainment Tonight though, Hamm and Westfeldt ended their relationship of almost two decades because the latter was sick of the former’s partying ways.
“They were together for many years, but in the end, it was too much work. It’s no secret that Jon likes to go out and leads a very party-heavy lifestyle. And Jennifer was just tired of that,” a source said. “She was tired of being his mother.”