Jon Hamm and Anna Osceola's Post-Wedding Plans: Exciting Talks of Starting a Family!

Jon Hamm and Anna Osceola recently got married, but a trusted source reveals that they are already contemplating the next step in their relationship.

According to the insider, the couple is considering starting a family in the near future. In the latest edition of We, the source shares exclusively, "Jon and Anna are thinking about having children soon. Jon believes that this marks the beginning of a new chapter in his life. He is in a content and healthy state, and his friends are delighted to witness him in this blissful state."

The 52-year-old Mad Men star and his 35-year-old partner tied the knot in an outdoor ceremony at Anderson Canyon in Big Sur, California on Saturday, June 24. Interestingly, this location holds significance as it featured prominently in the series finale of Mad Men, in which Don Draper (played by Jon Hamm) found inspiration for the iconic “I’d Like to Buy the World a Coke” ad while staying at the retreat. Coincidentally, Osceola played the receptionist at this very venue.

The couple's nuptials were an amazing celebration, with a lively dance floor that kept the energy levels high, according to a second insider. The star-studded guest list included John Slattery, Hamm's Mad Men costar, as well as Tina Fey, Paul Rudd, Larry David, Billy Crudup, and Brooke Shields.

Although Hamm and Osceola were briefly connected in 2017, their relationship was confirmed by Us in 2020. Their first public appearance together was at an Oscars party in March 2022. They also had the opportunity to reunite onscreen in the film Confess, Fletch later that year.

Jon Hamm and Anna Osceola. Matt Baron/BEI/Shutterstock

Hamm insinuated in a September 2022 interview with Howard Stern that his romance was reaching a profound level. During the interview, Hamm expressed feelings of comfort and a sense of mutual care in the relationship. He confidently stated that he could definitely envision marrying Osceola. In response to Stern's inquiry about his love for Osceola, Hamm emphatically affirmed that he is deeply in love with her.

In February, it was confirmed to Us by an insider that the couple had become engaged some time ago. The insider also mentioned that they have a great time together and already feel like they are married.

Before being in a relationship with Osceola, Hamm was in a relationship with Jennifer Westfeldt for 18 years. The former couple ended their relationship in September 2015. A source informed Us at the time that they made efforts to stay together, but there was always a disagreement between them. The insider revealed that Hamm wanted children while Westfeldt did not.

For more on Hamm and Osceola’s newlywed bliss, watch the video above and pick up the new issue of We, on stands now.