Jon Hamm is preparing to become a father for the first time at age 55, as his wife, actress Anna Osceola, is pregnant with their first child. Osceola, 38, was seen displaying a visible baby bump during a beach day in the Hamptons with Hamm.

The couple, who wed in 2023, were first reported to be expecting in late June, with an eyewitness spotting Osceola's pregnancy during a vacation in Ischia, Italy.

This news marks a shift for Hamm, who previously expressed reservations about fatherhood. In a 2008 interview with The Guardian, he stated, "I don't necessarily want kids. A lot of our friends are having children and I don't know if it's for me." He elaborated that his upbringing, marked by the early death of his mother, made him uncertain about the experience of having children.

Hamm and Osceola met in 2015 on the set of "Mad Men," where Osceola had a guest role. Hamm was in a long-term relationship with Jennifer Westfeldt at the time, and the couple announced their separation in September 2015. Hamm and Osceola were first publicly linked in 2017 and confirmed to be dating in 2020. They made their red carpet debut in 2022 and announced their engagement in February 2023.

In a June 2024 interview, Hamm reflected on his current life, stating that his relationship with Osceola had brought him to a place of stability. He credited therapy for helping him address childhood trauma, which he said opened up the possibility of marriage and starting a family. "It sounds hokey and whatever, but it's real and for one of a better word, it's what I'm working for," he said at the time. He also noted his age, anticipating being an "old dad."