Jon Hamm Divorced? His History of Marriage, Explained

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When you take getting married seriously enough, getting divorced becomes less likely.

Jon Hamm has been both married and divorced over the years.

But considering his reputation for being handsome and charming and his successful career, you might be surprised by how seriously he takes long-term relationships.

Here’s a look at his marriages, his splits, and where things stand today.

Jennifer Westfeldt (1997 – 2015)

In the ’90s, Jon first met actress and screenwriter Jennifer Westfeldt at a mutual friend’s birthday party.

They started off running lines together — ostensibly because Jennifer did not know any other men in town to run lines with for an upcoming audition.

She didn’t get that part, but they did hit things off.

They married in 1997, beginning an 18-year marriage.

Over time, Jon and Jennifer co-starred in Gap ads, and even formed a production company together: Points West Pictures.

Because Jon and Jennifer were both working actors, they found a way to make things work over long distance.

Actors have wildly varying schedules and sometimes must be on set at late hours or in different time zones for months at a time.

However, it did not last forever.

In 2015, the two divorced. Jon openly spoke about how low it felt to be single after being in a relationship for so long.

We should not view a divorce after 18 years as a failure, however. That’s a long, successful marriage. And it also only part of Jon’s story.

Anna Osceola (2020 – ????)

In 2014, the series finale of Mad Men filmed, airing in 2015.

Actress Anna Osceola had a small role in the episode — portraying a flower child receptionist at the California coastal retreat where Jon’s character, Don Draper, stayed.

Fast-forward six years to 2020, and Jon and Anna officially began dating.

In 2022, they took things a step further, becoming engaged.

In June 2023, Jon and Anna married at Anderson Canyon in Big Sur — at the same location where the scene filmed, just around the 9th anniversary of its filming. At the time, they were barely co-stars — and could not have guessed what would one day develop.

Jon Hamm and Anna Osceola are still together today.

There’s even an exciting twist to their relationship.

In August of 2026, news broke that Anna was pregnant with the couple’s very first child!

They have also worked together again — on Your Friends & Neighbors for Apple TV.

One divorce in two marriages isn’t bad, especially considering Jon’s age and career.