Jon Hamm and Anna Osceola expecting their first child together

Jon Hamm and Anna Osceola are entering an exciting new chapter as they prepare to welcome their first child together.

The couple, who have been married for two years, recently sparked pregnancy reports after Osceola was spotted showing off what appeared to be a growing baby bump during a beach outing in the Hamptons. The 38-year-old actress enjoyed a relaxing day by the water with her 55-year-old husband, who appeared equally happy to spend quality time with her.

Osceola was photographed wearing a dark green bikini that highlighted her growing belly. She appeared to be enjoying the summer weather as she took a dip in the ocean before spending more time with Hamm on the beach. The actor was seen wearing shorts as he stayed close to his wife and appeared to help care for her during their outing.

If confirmed, the pregnancy would mark a major milestone for the couple, particularly because Hamm has previously spoken openly about not being certain that he wanted to become a father.

In a 2008 interview, when Hamm was 35 and in a relationship with actress Jennifer Westfeldt, the actor admitted that having children was not necessarily part of the future he had imagined for himself. He explained that although many of his friends were starting families, he was unsure whether parenthood was something he wanted.

Hamm also reflected on how a person’s family background could influence their views on having children. At the time, he said he had not firmly decided either way and was still uncertain about whether parenthood would be the right path for him.

His perspective appeared to change significantly after meeting Osceola.

Jon Hamm and Anna Osceola’s relationship

Hamm and Osceola first crossed paths in 2015 while working together on the final season of the popular television series Mad Men. Although they met several years earlier, their relationship did not become romantic immediately.

The pair were first linked romantically in 2017 before their relationship became more serious and they were publicly confirmed as a couple in 2020.

In 2022, Hamm and Osceola made their red-carpet debut together at an Oscars viewing event. Around the same period, Hamm opened up about how his relationship with Osceola had changed his outlook on marriage and family.

The actor previously revealed that being with Osceola helped him discover a different kind of happiness and made him reconsider some of his earlier thoughts about marriage and having children.

Hamm and Osceola announced their engagement in February 2023. Just a few months later, they exchanged vows in June at Anderson Canyon in Big Sur, California. The location held special meaning for the couple because it was also where they had first met while filming Mad Men.

Now, with reports of their first baby on the way, the couple appear to be preparing for one of the biggest changes in their relationship yet. Their journey from co-stars to partners and eventually husband and wife has already marked several important milestones, and parenthood could soon become their newest chapter.