While we’ll never know what really happened between Jon Hamm and Jennifer Westfeldt, Hamm left enough bread crumbs along the way to indicate that he was the one who never wanted to get married. He used to say he didn’t believe in marriage, that it was all a sham. Hamm and Westfeldt spent 19 years together – she was with him when he was nobody, when he had no power and no job and she was the one supporting him. Then, just as Mad Men was coming to a close, they fell apart. He quickly moved on with Anna Osceola and they got married in Big Sur last weekend after dating for maybe five years? While everybody is allowed to change their minds and grow and become different people, I still f–king loathe when men do this – bitch about marriage for years and then suddenly get married and they act like they invented it. Well, Hamm had a lot to say about the beauty of marriage on a podcast recorded just before his wedding:
Jon Hamm, 52, appeared on Tuesday’s episode of iHeartRadio’s Table for Two podcast with host Bruce Bozzi, and the actor referred to his marriage to Osceola, 35, as “the exciting part of life and it’s a signpost and a signifier of the next chapter and phase [of life]. Ideally, it gives you and your partner a sense of stability and comfort and an identifying capacity that is better, deeper, richer, than ‘it’s my girlfriend’ or ‘my boyfriend’ or what have you.”
“It’s exciting, it’s exciting because it’s all potential, it’s all possibility, and it’s all positive,” Hamm said on the podcast episode, which was recorded in the days leading up to his wedding.
“I suppose there’s two ways to look at anything like that, which is like ‘oh, what if it’s terrible, but the other way is like ‘this is meant to be something wonderful.’ So you lean into that aspect of it, which I have been,” he continued during the interview. “It’s the reason why I really wanted to do it and really leaned into it and [marriage] is the thing that leads to the next thing of life and that’s what I hope – and it’s the journey and it’s exciting.”
While Hamm noted that “all of the minutiae of planning [a wedding] and dealing with it can be mind-numbing,” he said he felt “a sort of calm [that] settled over me” in the days leading up to the ceremony as he began to reflect on what the ceremony would signify for his life.
“At the end of the day, the important thing is… I’m gonna look out and I’m gonna see this whole group of people – and it’s not a very big group of people. It’s well, under 100 people – but a group of people that are all there because they’re supporting me and Anna,” he said during the podcast. “And that’s great. I think the last time that happened to me was high school graduation.”
Again, people are allowed to change their minds, but damn, I feel so sorry for Jennifer Westfeldt. She wasted so many years on this loser. Oh, and to make matters even more cliche, Us Weekly reports that Hamm and Osceola are “thinking of having kids soon, Jon feels like this is the beginning.” Beginning a marriage and a family at 52 years old… that’s something women are rarely able to do.
Photos courtesy of Avalon Red.
Jon Hamm and Anna Osceola attends the 2022 Vanity Fair Oscar Party Hosted By Radhika Jones celebrating the 94th annual Academy Awards at the Wallis Annenberg Center for the Performing Arts on March 27, 2022 in Beverly Hills, California,Image: 673516037, License: Rights-managed, Restrictions: , Model Release: no, Pictured: Jon Hamm and Anna Osceola, Credit line: – / JPI Studios / Avalon 
SAN DIEGO, CALIFORNIA, USA – MAY 04: Jon Hamm and Anna Osceola arrive at the World Premiere Of Paramount Pictures’ ‘Top Gun: Maverick’ held at the USS Midway Museum on May 4, 2022 in San Diego, California, United States.,Image: 688800390, License: Rights-managed, Restrictions: , Model Release: no, Pictured: Jon Hamm, Anna Osceola, Credit line: Xavier Collin / Image Press Agency / Avalon 
HOLLYWOOD, LOS ANGELES, CALIFORNIA, USA – JULY 20: American actor Jon Hamm and girlfriend/American actress Anna Osceola arrive at the 2022 ESPY Awards held at the Dolby Theatre on July 20, 2022 in Hollywood, Los Angeles, California, United States.,Image: 708815165, License: Rights-managed, Restrictions: , Model Release: no, Pictured: Jon Hamm, Anna Osceola, Credit line: Xavier Collin / Image Press Agency / Avalon
Jon Hamm, Anna Osceola attends the 2023 Vanity Fair Oscar Party Celebrating the 95th Annual Academy Awards Hosted By Radhika Jones at Wallis Annenberg Center for the Performing Arts on March 12, 2023 in Beverly Hills, California,Image: 762328867, License: Rights-managed, Restrictions: , Model Release: no, Pictured: Jon Hamm, Anna Osceola, Credit line: – / JPI Studios / Avalon 
BEVERLY HILLS, CALIFORNIA – MARCH 12: (L-R) Jon Hamm and Anna Osceola attend the 2023 Vanity Fair Oscar Party hosted by Radhika Jones at Wallis Annenberg Center for the Performing Arts on March 12, 2023 in Beverly Hills, California.,Image: 763053994, License: Rights-managed, Restrictions: , Model Release: no, Pictured: Jon Hamm, Anna Osceola, Credit line: Jeffrey Mayer / AvalonncG1vNJzZmivp6x7pLHLnpmirJOdxm%2BvzqZmcWpjbYRxe8mopZigkaK6oLrOsJabnZyesrex0pikmqqinq6osb6iqpiclZq9pr6%2Bq6CcoJWnrLW0wKeWo62jqaylrdOipaBn