From On-Screen Chemistry to Real-Life Romance: Unveiling the Unforgettable Love Story of Jon Hamm and Anna Osceola

Jon Hamm, known for his award-winning role as Don Draper on Mad Men, not only received critical acclaim but also found love on the set of the popular TV show. Hamm's on-screen chemistry eventually led him to his wife, Anna Osceola.

During the filming of the series finale of Mad Men in 2015, Hamm and Osceola crossed paths as their characters interacted. Osceola portrayed Clementine, a receptionist at the retreat attended by Hamm's character. Although there were rumors of a brief fling in 2017, it was not until June 2020 that we were able to confirm their romantic relationship. After nearly three years of dating, Hamm decided to take their commitment to the next level by proposing to Osceola.

According to a source who spoke to Us in February 2023, the engagement between the couple took place some time ago, but they are still extremely happy and excited. They have a great time together and already feel like a married couple.

Even though they are not active on social media, the couple has shared many enjoyable moments throughout the years. They have made appearances on the red carpet, enjoyed vacations in Europe, worked together on-screen again, and much more. It seems that staying away from the public eye has worked for them. In fact, during an interview on The Howard Stern Show in September 2022, the star of Top Gun: Maverick expressed that he can definitely see himself settling down with Osceola.

Describing their relationship as "comfortable," the former Unbreakable Kimmy Schmidt star expressed to Howard Stern, "It's a sense of nurturing and being nurtured, of mutual support. It has also involved a journey of self-improvement, prioritizing my mental well-being, and addressing the trauma from my past with the help of therapy. Through this process, I've come to realize that losing someone so significant, like my mother at a young age, creates a deep emotional scar that can hinder emotional connection and vulnerability."

Hamm shared with ABC News in October 2016 that he tragically lost his mother, Deborah Hamm, to colon cancer when he was just 10 years old.

He went on to say, "Only in recent years, as I've taken time to reflect on these experiences, has my current relationship gained even deeper significance. It has opened up new possibilities for marriage, parenthood, and a redefined sense of happiness, fulfillment, and overall well-being. I know it may sound cliché, but it is genuine and true."

Hamm and Osceola exchanged vows in June 2023, promising their forever in a picturesque outdoor wedding at Anderson Canyon in Big Sur, California.

Hamm had been in a committed relationship with actress Jennifer Westfeldt for 18 years prior to his relationship with Osceola. They had been together since 1997 but decided to part ways in September 2015. According to a source, despite their efforts to mend their relationship, there was always a fundamental difference between them - Hamm desired to have children while Westfeldt did not share the same desire.

The actor from Good Omens discussed their breakup candidly in a June 2017 interview with InStyle. He expressed that being single after a long-term relationship was a difficult adjustment. The actor emphasized the challenges and expressed his discontent.

Credit: Matt Baron/BEI/Shutterstock

Jon Hamm and Anna Osceola's Relationship Timeline: From 'Mad Men' to Their Marriage and More

Mad for each other. Not only did Jon Hamm win an Emmy for his role as Don Draper on Mad Men, but the show introduced him to his wife, Anna Osceola.

The actors crossed paths during the production of the final episode of the AMC drama in 2015. Osceola portrayed Clementine, a receptionist at the retreat attended by Hamm's character. While their relationship was briefly speculated about in 2017, the couple's romance was officially confirmed by us in June 2020. After nearly three years of dating, Hamm took their relationship to the next level by proposing to Osceola.

According to a source, the engagement actually took place some time ago but the couple is still elated. They enjoy each other's company immensely and already feel like a married couple.

Although they are not present on social media, they have shared numerous enjoyable experiences throughout the years. These include attending red carpet events, going on European vacations, working together on screen, and more. Keeping a low profile seems to have had a positive impact, as the star of Top Gun: Maverick revealed during an appearance on The Howard Stern Show in September 2022 that he could envision himself settling down with Osceola in the future. Describing their relationship as "comfortable," the former cast member of Unbreakable Kimmy Schmidt explained to host Howard Stern that it involves taking care of one another and receiving care in return. It has also been a journey of self-improvement, mental health, and therapy for him, as he has been unpacking and addressing the trauma of losing someone important to him, like his mother, at a young age. Hamm shared with ABC News in October 2016 that his mother, Deborah Hamm, passed away from colon cancer when he was just 10 years old.

In a recent reflection, he expressed, "Only recently have I taken the time to truly reflect on and appreciate all that has contributed to the meaningful relationship I am currently in. This has not only opened my mind to the possibility of marriage and starting a family, but it has also allowed me to redefine my perception of happiness, life, and overall well-being. Though it may sound clichéd, these aspects hold genuine significance to me."

In a picturesque outdoor ceremony at Anderson Canyon in Big Sur, California, Hamm and Osceola exchanged vows and officially became husband and wife in June 2023.

Before Osceola, Hamm had been in a lengthy 18-year relationship with actress Jennifer Westfeldt. From 1997 until September 2015, the couple were together before ultimately deciding to end their relationship. According to a source, despite their efforts to work things out, there was always a noticeable tension between them, with conflicting desires for children being a significant factor.

In a candid interview with InStyle in June 2017, the Good Omens actor spoke about the aftermath of the breakup. He expressed that while he was coping, it was no easy feat to adjust to being single after spending such a long time in a committed relationship. Indeed, he described the experience as difficult and acknowledged the challenges and disappointments that come with it.

Scroll below to relive Hamm and Osceola’s sweetest relationship moments:

Credit: Justina Mintz/AMC

2015

The two first met while filming the season finale of AMC's Mad Men, which aired on May 17, 2015.

Credit: MEGA

2017

The pair were spotted together for the first time off-screen exiting a coffee shop.

Credit: P&P/MEGA

May 2020

Three years later, Hamm and Osceola were spotted in public again, playing tennis together in Los Angeles.

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June 2020

A month later, Us confirmed that the couple were officially dating.

Credit: MEGA

September 2020

Later that year, the two soaked up the sun while enjoying a day at the beach in Santa Barbara, California.

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September 2021

The stars took their romance abroad and soaked up the sun during their vacation in Italy.

Credit: Casey Flanigan/imageSPACE/Shutterstock

March 2022

Nearly two years after publicly declaring their relationship, Hamm and Osceola stepped onto the red carpet for the first time as a couple. The memorable occasion took place at a star-studded Oscars viewing party held by none other than Mercedes-Benz, a brand that Hamm proudly represents as an ambassador.

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May 2022

The happy couple made another red carpet appearance at the premiere of Sarah Silverman's musical Bedwetter in New York City.

Credit: Matt Baron/Shutterstock

September 2022

Hamm revealed details about his romantic life during an appearance on The Howard Stern Show. He confessed that his relationship with Osceola felt incredibly comfortable, describing it as a beautiful balance of caring for each other. Furthermore, Hamm acknowledged the role that therapy played in helping him address past trauma and become more open and emotionally accessible.

He exclaimed, "It has only been within the past few years that I have taken the time to deeply contemplate all of these aspects, and it has truly enhanced the significance of my current relationship. It has also opened up the realm of possibilities, including the prospect of getting married, having children, and redefining what it means to experience happiness, lead a fulfilling life, and prioritize wellness. I know it may sound cliché or cheesy, but these are the real and genuine aspirations I have now."

Credit: Kathy Hutchins/Shutterstock

September 2022

Seven years after their memorable collaboration on Mad Men, Jon Hamm and Bruce Osceola reunited on the big screen in the hilarious comedy Confess, Fletch. In this film, Hamm portrayed the lead character, Irwin M. Fletcher, a renowned journalist, while Osceola brought his talent to the role of Larry.

Credit: Matt Baron/BEI/Shutterstock

February 2023

A source has confirmed that the couple is engaged, stating, "The engagement took place some time ago, and they are still filled with joy and happiness. They enjoy each other's company immensely and already feel like a married couple."

Credit: Matt Baron/BEI/Shutterstock

March 2023

One month after news broke of their engagement, the twosome stepped out in Hollywood for the Vanity Fair Oscar Party.

Credit: Adela Loconte/Shutterstock

June 2023

The lovebirds said "I do" at an outdoor wedding in Big Sur, California, in front of family and friends, including John Slattery, Paul Rudd and Tina Fey.