Anna Osceola is Jon Hamm's first wife, but what about Jennifer Westfeldt?
Anna Osceola became Jon Hamm's first wife after they exchanged vows in June 2023. But before that, the Mad Men alum had been in an 18-year relationship with Jennifer Westfeldt. In a joint statement to People in September 2015, the ex-couple announced their split, revealing:
It is with great sadness that we have decided to separate after all these years of shared love and history. Nonetheless, we will continue to support each other in every possible way moving forward.
Source: Getty Images
TABLE OF CONTENTS
Key takeaways
- Jon Hamm and Jennifer Westfeldt were in a romantic relationship from 1997 to 2015.
- Westfeldt supported Hamm during his 30-day stint in rehab for alcoholism in early 2015.
- In 2023, Jon Hamm became engaged to Anna Osceola after dating for two years.
- Jennifer Westfeldt is reportedly single.
Jennifer Westfeldt was not Jon Hamm's first wife
Hamm and Westfeldt met in 1997 at a birthday party hosted by a mutual friend. In a 2011 chat with The Hollywood Reporter, the former hilariously narrated how they later reconnected after she requested him to help her read lines for a potential film. He said:
We officially met so that I could assist her in preparing for an audition she had landed for the film Zero Effect. Apparently, I was not that good; she did not get the part.
Jennifer and Jon started dating but never married. Nonetheless, they both often expressed their deep commitment to each other. Hamm told Parade in 2010:
I do not have a marriage chip, but after 10 years, Jen is more than just my girlfriend; she is the love of my life.
Speaking with Playboy in 2012, per Daily Mail, Hamm revealed that he does not believe in marriage, stating:
My parents divorced when I was two and never remarried. I do not have that paragon of married life to look at and think, "That is what I want!"
Source: Getty Images
Jon and Jennifer frequently collaborated professionally
Jennifer and Jon co-starred in the films Ira & Abby, Friends with Kids and Kissing Jessica Stein, which the former wrote.
In April 2009, they launched their own production company, Points West Pictures. Hamm praised Westfeldt's work ethic during a 2012 interview with Beauty and the Dirt, saying:
Jen has worn the hats of writer, director, producer and actor in various projects. In all, she always leads by example.
The pair split after being together for nearly two decades
After Jon and Jennifer announced their separation in 2015, a source close to him told People that his party-heavy lifestyle contributed to it.
Jen was more of a mother figure than a girlfriend to Jon. They broke up after he got sober and did not need to lean on her to take care of him.
Another source told Entertainment Tonight of the reason behind the pair's split:
They were together for years, but in the end, it was too much work. Jennifer was tired and wanted him to grow up.
Nonetheless, the exact reason why Hamm and Westfeldt split remains speculative, as neither has publicly addressed it.
Source: Getty Images
Jon Hamm found love again in Anna Osceola
According to People, Jon and Anna met in 2015 on the set of Mad Men. However, they reportedly did not connect romantically until 2020. The duo made their red-carpet debut during the 2022 Oscars afterparty.
Hamm and Osceola got engaged in February 2023. In June 2024, he shared with The Hollywood Reporter how he was "terrified" to pop the big question after growing up with divorced parents, revealing:
It was scary, but I knew that meant it was worthwhile.
Their relationship changed his perception of marriage and parenthood
Days before his wedding with Anna, Jon told host Bruce Bozzi on the Table for Two podcast that marriage was the next exciting chapter of his life.
Marriage gives you and your partner a sense of stability and comfort that is deeper and richer than that of a casual relationship.
Osceola and Hamm exchanged nuptials on 24 June 2023 at Anderson Canyon in Big Sur, California. Attendees included Tina Fey and Billy Crudup.
In his interview with The Hollywood Reporter, Jon, who once did not have a "driving force to have a baby", revealed he is open to fatherhood, saying:
It is not lost on me; I could be the old dad. It could be a good thing.
Source: Getty Images
Osceola and Hamm co-starred in Confess, Fletch
In 2022, the pair appeared on screen together for the third instalment of the Fletch series. They both stay off social media, choosing to keep details about their relationship private. Speaking with InStyle in 2017, Jon, in part, disclosed the reason behind their decision, stating:
Posting photos online for everyone to see is a fun experience. However, there is no point beyond immediate gratification.
FAQs
Jon is best known for his Emmy Award-winning role as Don Draper in Mad Men. Here are some frequently asked questions about him:
How old is Jon Hamm?
Hamm (54 as of 2025) was born on 10 March 1971 in St. Louis, Missouri, USA. His parents are the late Deborah and Daniel Hamm. Jon is of English, French, German and Irish descent.
What is the age gap between Jon Hamm and his wife?
Anna Osceola (37 as of 2025) was born on 8 April 1988. She is 17 years younger than her husband, Jon Hamm.
Source: Getty Images
What is Jon Hamm's net worth?
According to Celebrity Net Worth, Jon has an estimated net worth of $45 million. His wealth primarily stems from his successful acting career that spans over two decades.
Wrapping up
Anna Osceola became Jon Hamm's first wife after his split from his girlfriend of 18 years, Jennifer Westfeldt. The ex-pair started dating in 1997, around the time they were both starting their Hollywood careers, but split in 2005.
READ MORE: Who is Harlene Rosen?
Briefly.co.za highlighted facts about Woody Allen's first wife, Harlene Rosen. The controversial comedian married her in the late 1950s when he was starting his career as a comedy writer.
Harlene and Woody divorced after six years, and she famously sued him for defamation when he said mean things about her in his stand-up acts.
Proofreading by Kelly Lippke, copy editor at Briefly.co.za.
Source: Briefly News
