Jon Hamm and Anna Osceola Are ‘Ready’ for First Baby—but Will ‘Mad Men’ Star’s Bachelor Pad Serve as Their Family Home?

“Your Friends & Neighbors” co-stars Jon Hamm and Anna Osceola are reportedly gearing up to become first-time parents, three years after they tied the knot in an intimate cliffside ceremony in California.

The happy couple, who met on the set of "Mad Men," first sparked speculation that they were expecting after Osceola, 38, was seen with a baby bump during a trip to the Hamptons—with sources quickly confirming to People magazine that Hamm, 55, and his spouse were happily preparing to welcome a child.

“Jon’s incredibly excited,” the unnamed insider said. “This is something he and Anna have wanted and hoped for. He’s not thinking about his age or what anyone else has to say about it. He’s just really happy.”

The source added that Hamm feels "happy, settled, and ready" for the next stage of his life, while a different insider told Us Weekly that the couple has "been trying to relax a bit but are enjoying making plans for the baby."

While the process of nesting can look entirely different from one family to the next, the news about Hamm and Osceola's pregnancy does raise a question about whether the couple will raise the baby in the actor's longtime $4 million Los Feliz pad, which he purchased in 2017, before he was officially linked with his now-wife.

Though the home served as a bachelor pad for Hamm for several years, it has since become a marital residence for the couple—and could now evolve once again into a family dwelling.

Certainly the four bedroom, 3,600-square-foot home boasts plenty of room for a family of three. There's a spacious kitchen equipped with top-of-the-line appliances and a spacious pantry.

The 4.5 bathrooms feature spa-like furnishings and the comfortable family room opens up to a stunning backyard patio complete with a built-in grill station, fire pit, and saltwater pool.

The property’s midcentury aesthetic makes it the kind of place one might picture the actor’s most notable on-screen character, Don Draper, residing, with wood paneling and asymmetrical design choices that ooze character while maintaining a peaceful environment.

The gated property is located at the end of a charming cul-de-sac in the Los Angeles neighborhood, which many big names in Hollywood have called home over the years, including Brad Pitt, Kristen Wiig, and Aubrey Plaza.

It’s not the first time Hamm has invested in the area, purchasing a 3,100-square-foot Los Feliz abode for $900,000 in 2002 with his then-partner, actress Jennifer Westfeldt. The duo parted ways in 2015 after spending 18 years together.

During his previous relationship, Hamm was not sold on the concept of fatherhood. “I see my friends who have children and I’m like, ‘Dude, how are you even upright, much less here at work at 6 a.m.?” he candidly said to Us in 2012.

However, he’s changed his tune since beginning a life with Osceola and is now “over the moon” at the thought of becoming a dad, according to an Us Weekly source.

“Jon has always wanted to be a dad with Anna,” the source continued. “Having a family was something that was really important to both of them from the beginning.

"They’ve talked about this chapter for a long time and were always on the same page about wanting children, so for it to be actually happening now feels incredibly special.”

The Emmy-winning performer has opened up about his desire to have a family with his wife, telling The Hollywood Reporter that, due to his parents’ divorce during his childhood, he “didn’t look at marriage as a thing,” but was hopeful for his own union to turn into a growing family.

“I will be the old dad, but so it goes,” he said in 2024, then 53 years old. “It could be a good thing. We’ll see.”

Hamm and Osceola first crossed paths in 2015, when filming the finale episode of “Mad Men” in Big Sur, CA.

Romance rumors swirled in 2017, but their relationship was not officially confirmed until 2020. The couple made their public red carpet debut at the Vanity Fair Oscars Party in 2022.

Hamm eventually popped the question. “I just knew at a certain point I wanted to be with this person,” he shared with The Hollywood Reporter in 2023. “But when I proposed, I was terrified. I was like, ‘What am I doing?’”

The couple tied the knot in July 2023, with their sentimental wedding celebration serving as a thoughtful nod to their “Mad Men” roots.

The ceremony was held at Anderson Canyon, the Big Sur spot where they first met when filming the show’s final episode. Surrounded by loved ones and lush florals, they exchanged vows alongside the Pacific Ocean.