Who Is Jon Hamm's Wife? All About Anna Osceola As The Couple Gears Up To Welcome Their First Child

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Anna Osceola is pregnant! The news that the actress and her husband, Jon Hamm, are expecting their first child started making headlines on August 10, 2026 (ET) after several news outlets reported the same. The joyous news came three years after they tied the knot, and fans could not be any happier. Amid that, let's take a look at some lesser-known facts about Anna.

Anna Osceola and Jon Hann are expecting their first child

Jon Hamm and Anna Osceola are going to be parents soon. The news started making rounds on August 10, 2026 (ET) after the Daily Mail reported that the actress was seen showing off her baby bump. Anna was spotted in a bikini during a trip to the Hamptons with her husband when her adorable bump and pregnancy glow caught everyone's attention. 

The news comes three years after Jon and Anna tied the knot in a picturesque wedding. The couple allegedly dated for a while before getting hitched in 2023, and now they are all set to hop on to the parenthood train. The couple has an age gap of 17 years, as Jon Hamm, as of 2026, is 55 years old, whereas Anna Osceola is 38 years old. Jon had previously expressed an interest in parenthood in a 2024 interview with The Hollywood Reporter. He said:

"It's not lost on me that I'm 53. I will be the old dad, but so it goes. It could be a good thing. We'll see."

Who is Jon Hamm's wife, Anna Osceola?

Anna Osceola was born in Cambridge, Massachusetts, USA, on April 8, 1998. The actress relocated to California to pursue acting. Anna is a well-known actress who rose to fame with her 2007 project Not Another High School Show. She played the role of 'Charlie' in the TV movie.

Anna soon became a household name and even appeared in a number of episodes of the ABC Family series Greek as 'Robin Wylie' between 2008 and 2009. Most recently, Anna played 'Noelle Terlesky' in the TV mini-series Law & Order True Crime in 2017. After that, she took a role in 2022's Confess, Fletch.

Talking about her personal life, Anna Osceola first met her now-husband, Jon Hamm, on the set of Mad Men. The actress played 'Clementine', a receptionist at the retreat Jon's character 'Don Draper' attended in the series finale. Although Anna made a limited appearance in the final episode, she certainly made an impression on viewers and her cast members, especially Jon. The couple was seen again in 2017, this time off-camera, when they decided to hang out two years after Mad Men ended.

Then, as quarantining for many across the country took full effect in March 2020, the two were spotted again picking up some food, according to Extra. Romance soon bloomed between the two, and they tied the knot in 2023. However, Anna Osceola was not Jon Hamm's first famous romantic partner. Jon was in a long-term relationship with Jennifer Westfeldt from 1997-2015. Jon previously spoke in interviews about the depth of their relationship, but by 2015, their romance had run its course. 

A few years later, in 2019, Jon Hamm was spotted in New York City with Lindsay Shookus, who was previously linked to Ben Affleck. They attended a Broadway show together as well as an after-party for Saturday Night Live. However, even that relationship came to an end, as Jon and Anna Osceola found their way to each other.

What are your thoughts on Anna Osceola? Let us know.

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