Whenever I express sympathy for Jennifer Westfeldt, people yell at me and argue that I’m wrong to feel sorry for her for the way things shook out with Jon Hamm. Well, I’m about to do it again. Jennifer Westfeldt and Jon Hamm were together for 18 years and they famously never married. They got together in 1997, when he was a nobody who could not get a job and she was the breadwinner of their relationship. A decade later, he got Mad Men. She was with him when he became a household name and an in-demand, award-nominated actor. She was with him when he struggled with a drinking problem and she actually stayed with him when he sought treatment. They broke up several months after he left rehab, in 2015. He quickly jumped into a relationship with Anna Osceola, whom he met during Mad Men’s final season. Jon and Anna married in 2023, and now they’re expecting their first child.
Jon Hamm and Anna Osceola are going to be parents!
The Mad Men actor and Osceola are expecting their first baby together, a source confirms to PEOPLE.
Reps for both Hamm, 55, and Osceola, 38, could not be reached for comment. Daily Mail was first to report the news that the couple are expecting their first child.
Hamm and Osceola’s happy news comes a few years after the Your Friends & Neighbors costars tied the knot in June 2023.
Congrats to them. A first-time father at 55? Okay. But they have money and stability and I’m sure everything will work out well. Still, though… man, I hope Jennifer Westfeldt is doing alright. She’s still around, she still books the occasional TV job. I’ve always wondered if Jon gave her some kind of quiet financial settlement when they split, because damn, they were together for a long time and they were effectively in a common-law marriage.
Photos courtesy of Avalon Red.
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- MUSEUM ROW, MIRACLE MILE, LOS ANGELES, CALIFORNIA, USA – MARCH 15: Anna Osceola and Jon Hamm arrive at the 2026 Vanity Fair Oscar Party (98th Annual Academy Awards) Hosted By Mark Guiducci held at the David Geffen Galleries at the Los Angeles County Museum of Art (LACMA) at 5905 Wilshire Blvd on March 15, 2026 in Museum Row, Miracle Mile, Los Angeles, California, United States.,Image: 1083789742, License: Rights-managed, Restrictions: , Model Release: no , Pictured: Anna Osceola, Jon Hamm , Credit line: Xavier Collin/Image Press Agency/Avalon
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- 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
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- 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 / Avalon
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- Jon Hamm mit Ehefrau Anna Osceola bei der Vanity Fair Oscar Party 2024 anlässlich der 96. Oscar-Verleihung im Wallis Annenberg Center for the Performing Arts. Beverly Hills, 10.03.2024 *** Jon Hamm with wife Anna Osceola at the Vanity Fair Oscar Party 2024 on the occasion of the 96th Academy Awards at the Wallis Annenberg Center for the Performing Arts Beverly Hills, 10 03 2024 Foto:xJ.xBlocx/xFuturexImagex vanity_fair_1484,Image: 855966948, License: Rights-managed, Restrictions: imago is entitled to issue a simple usage license at the time of provision. Personality and trademark rights as well as copyright laws regarding art-works shown must be observed. Commercial use at your own risk., Model Release: no, Credit line: IMAGO/Jennifer Bloc/Avalon
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- MUSEUM ROW, MIRACLE MILE, LOS ANGELES, CALIFORNIA, USA – MARCH 15: Anna Osceola and Jon Hamm arrive at the 2026 Vanity Fair Oscar Party (98th Annual Academy Awards) Hosted By Mark Guiducci held at the David Geffen Galleries at the Los Angeles County Museum of Art (LACMA) at 5905 Wilshire Blvd on March 15, 2026 in Museum Row, Miracle Mile, Los Angeles, California, United States.,Image: 1083789672, License: Rights-managed, Restrictions: , Model Release: no , Pictured: Anna Osceola, Jon Hamm , Credit line: Xavier Collin/Image Press Agency/Avalon
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- Jon Hamm attends the 2026 FOX Upfront, held at 151 West 55th Street in New York City, Monday, May 11, 2026.,Image: 1098200480, License: Rights-managed, Restrictions: Jennifer Graylock-Graylock.com, Model Release: no , Credit line: Jennifer Graylock/Avalon
*YAWN* beyond predictable.
My guess is that Jennifer Westfeldt has some complicated feelings about this. I hope she’s living her absolute best life.
I’m really glad so many women have resigned from raising a man and marrying for his potential. For too many generations, men have been trained to siphon life force off of others and it is a very good thing that that is changing.
Best of luck to Ms Osceola.
She has a baby face and looks more like his daughter than wife. She would have been mid 20s when they got together and would have looked very young which gives me the ick.
I’m sure they reached some sort of agreement financially. They were together 18 years.
Also, when he started making it big, he probably paid for all of the big expenses, like the mortgage, et cetera. So she probably was able to bank a lot of her earnings.
She’s almost 40 so a bit of an exaggeration. Still this whole thing sucks for Jennifer so I hope she is somewhere thriving.
Oof.
Obviously we don’t know anything about the breakup but I hope Jennifer is happy.
They broke up the same year he met Osceola on set for Mad Men. Hamm and Osceola supposedly weren’t dating until 5 years after that, their relationship first being made public in 2020. Yeah, I feel bad for Jennifer Westfeldt, too. She carried him emotionally and financially for at least a decade, stayed by him, and now he’s having a baby with someone else. Maybe JW didn’t/doesn’t care about having children. But if she did, then oof, this has to hurt.
Men are such obvious walking clichés.
Right??
38 is certainly better than 28, but *yawn*. We’ve seen this exact man in this exact scenario a million times in Hollywood and beyond.
Am I missing something? Why are we assuming Jennifer didn’t want the breakup? I can only imagine being exhausted carrying a man-child for so long — just because he seems to be doing well doesn’t mean she regrets the end of the relationship.
She could have wanted the break-up and felt relieved when the relationship ended. She could be very happy now, completely over her relationship with Jon and have zero regrets with how her life is now.
And she could STILL feel stung by the fact that he’s moved on to someone younger and more fertile.
None of these feelings are mutually exclusive because women’s feelings about procreation are often very layered and complex. And sometimes they’re not complicated at all, which is also OK.
I am very happily child-free but if my husband and I divorced and he went on to have kids with a younger woman I would have feelings about it that have nothing to do with my happiness in my own choices.
Why are these middle-aged guys (Hamm, Clooney) having babies in their 50s? (Or second families. Michael Douglas.) I am Hamm’s age. I cannot imagine staring a family at this age. (I don’t have kids; I’ve accepted that ship has sailed.)
Maybe their perspective on children changed when they met their current partners? Maybe they were in relationships previously where they had fertility problems? There are lots of reasons.
Men, in particular can have children later on. Maybe it looks different if you have unlimited resources and access to help.
Yeah, he’s a prick. Jennifer Westfelldt made a very sharp comedy I loved back in the day which critics shit on as a “rip-off” of Woody Allen films. Because no director is ever influenced by another and you always need to crush female directors who dare to take a thing from the “Masters,” pedophile or not.
I’ve never wanted to give birth and be a mother, and I suppose there are other women just like me, who don’t. I doubt Westfield is even thinking about Hamm.