Jon Hamm and Anna Osceola Share a Major New Chapter: Their First Baby Is on the Way

‘Mad Men’ Star Jon Hamm, 55, Set to Become a First-Time Dad as Wife Anna Osceola Expecting First Child

Jon Hamm and Anna Osceola are preparing to become parents for the first time. The Mad Men star and his wife are expecting their first baby together, according to a source who confirmed the news to PEOPLE.

Hamm, 55, and Osceola, 38, have been married since June 2023. The couple’s relationship has attracted attention over the years, particularly as Hamm has spoken openly about how his views on marriage and parenthood changed after finding a lasting relationship with Osceola.

Representatives for Jon Hamm and Osceola were not immediately available for comment. The pregnancy was first reported by the Daily Mail.

Jon Hamm and Anna Osceola Are Expecting Their First Baby

The upcoming arrival marks a new chapter for Jon Hamm and Osceola, who have built their relationship away from much of the public spotlight.

The couple first became romantically linked after working together on Mad Men. Osceola appeared in the series during its final season, while Hamm famously played advertising executive Don Draper throughout the show’s run.

Their relationship eventually developed into a serious partnership. In February 2023, Hamm and Osceola announced their engagement, and they married several months later.

The couple exchanged vows in June 2023 at Anderson Canyon in Big Sur, California. The location held a special connection to Hamm’s career because it was also used to film the finale of Mad Men.

Their wedding reportedly included several well-known friends and Hollywood figures, including actors Billy Crudup and Paul Rudd, as well as comedian and actress Tina Fey.

According to reports at the time, the couple also selected the theme from the 1967 James Bond movie You Only Live Twice as their walk-up song during the ceremony.

Hamm Previously Spoke About Having Children

Hamm has previously discussed the possibility of becoming a father with Osceola.

In a 2024 interview with The Hollywood Reporter, the actor reflected on his changing perspective toward marriage and family. He explained that his parents’ divorce when he was young had influenced his earlier views on marriage, saying that he had not always regarded it as something he expected to pursue.

Marriage to Osceola, however, changed that outlook.

Hamm said he hoped their marriage would eventually lead to having children. At the time, he also acknowledged that becoming a father later in life would mean being an older parent.

“I will be the old dad,” Hamm said, while acknowledging that possibility. He added that he was open to seeing how life developed.

His comments offered a glimpse into how significantly his priorities had evolved. For years, Hamm had been one of Hollywood’s most recognizable unmarried leading men, but his relationship with Osceola eventually led him to reconsider what he wanted from his personal life.

Jon Hamm and Anna Osceola’s Relationship

Hamm and Osceola have maintained a relatively private relationship, although the actor has occasionally shared his thoughts about their partnership.

During a 2022 appearance on Howard Stern’s SiriusXM show, Hamm described himself as in a settled, comfortable relationship with Osceola. He said the relationship had encouraged him to think more seriously about marriage, children, and what he wanted his future to look like.

At the time, Hamm described the relationship as meaningful and said it had opened the door to considering a different version of happiness and family life.

The couple subsequently became engaged and married in 2023, turning those earlier conversations about the future into reality.

Their first child will now add another major milestone to their relationship.

The Couple Have Also Worked Together

Jon Hamm and Osceola have continued to balance their personal relationship with their professional lives.

The pair recently worked together on the Apple TV+ series Your Friends & Neighbors. Hamm stars in the drama as Andrew “Coop” Cooper, a former hedge fund manager whose life takes an unexpected turn after losing his career.

Osceola plays Maggie Haber, a member of Coop’s neighborhood social circle.

In an interview with PEOPLE earlier this year, Hamm discussed what it was like to have his wife join the cast. Rather than viewing their shared workplace as complicated, he described the experience as enjoyable.

Hamm joked that working together also meant they could skip lengthy conversations about their respective workdays once they returned home.

The couple even occasionally brought their dog to set, giving them another opportunity to spend time together while filming.

A New Chapter for the Couple

The pregnancy comes three years after Jon Hamm and Osceola exchanged wedding vows and several years after Hamm first began publicly discussing the possibility of marriage and children.

For Hamm, the news represents a notable evolution in his personal life. The actor once expressed uncertainty about marriage, partly because of his childhood experience with his parents’ divorce. His relationship with Osceola ultimately changed that perspective and led to their engagement, marriage and now impending parenthood.

Professionally, Hamm remains active across television and film, while Osceola continues to build her acting career. Their work together on Your Friends & Neighbors has also allowed the couple to share the screen after their relationship moved from co-stars to life partners.

As they prepare to welcome their first child, Jon Hamm and Osceola are entering another significant stage of their relationship. While the couple has largely kept their private life out of the spotlight, their growing family marks a major milestone following their 2023 wedding.

Jon Hamm and Anna Osceola have not publicly announced additional details about the pregnancy, including the baby’s due date or sex.