Anna Osceola's Mad Men character hit it off with Jon Hamm's Don Draper

Eve Edwards September 21, 2022
Anna Osceola's Mad Men character hit it off with Jon Hamm's Don Draper


Former Mad Men star Jon Hamm has heaped praise on his current girlfriend Anna Osceola during his appearance on The Howard Stern Show, suggesting the pair might tie the knot soon – but did you know they met through working on the TV show?

WARNING: Details of the final episode of Mad Men will be discussed in this piece

Jon Hamm, 51, appeared on Howard Stern’s show this Monday, September 19 to talk all things love and relationships. Earlier this year saw Jon make his red carpet debut with current girlfriend Anna Osceola, despite the fact they have been dating for several years.

What you might be curious to learn is that Anna once held a minor role in Mad Men, which is where the two first interacted. Let’s revisit her character on the show.

Photo by Robin L Marshall/Getty Images

Who did Anna Osceola play in Mad Men?

Anna Osceola had a cameo in the final episode of Mad Men (season 7 episode 14, “Person to Person”). Her character’s name was Clementine and she starred as a receptionist who flirts with Hamm’s Don Draper.

Don goes to meet Stephanie, Anna Draper’s niece, at a Californian retreat in the final episode. When Stephanie packs up and leaves, taking the car with her, Don is stranded at the retreat.

Don tries to check out, asking if there are other cars able to take him back to the city, Clementine informs him that it isn’t possible for another few days. Instead, Clementine suggests Don attend one of the seminars which ultimately leads him to the spark of inspiration he needed to make the Coca-Cola commercial. So, is Clementine truly to thank for Don’s continued success?

Watch Anna and Jon Hamm’s characters interact in the final episode

Anna Osceola and Jon Hamm had chemistry from the get-go which you can see when watching their characters interact.

They first interact 24 minutes into the final episode. They have a one-on-one scene at 40 minutes when Anna Osceola’s character suggests Don Draper stays at the retreat.

If you’re wanting to stream Mad Men, it will cost you as currently the show is unavailable on streaming services without a charger. You can find Mad Men on Amazon and Apple TV.

When did Jon Hamm and Anna Osceola start dating?

After appearing in Mad Men together, the couple reportedly stayed in touch but things wouldn’t become serious until May 2020. They had been spotted out earlier, in 2017, grabbing coffee together, as reported by People. The pair hung out frequently in 2020, doing things like playing tennis and hanging out on the beach.

It was reported that Jon Hamm and Anna Osceola even quarantined together.

But Jon and Anna confirmed their relationship earlier this year, in May, when they appeared at the Vanity Fair Oscars party in March 2022. They later appeared at the Top Gun: Maverick premiere together, as Jon was one of the film’s stars. Since then, they have made numerous red carpet appearances and are seemingly going strong.

Jon says he’s ‘very much’ in love with girlfriend Anna

Appearing on The Howard Stern Show this month, Jon Hamm revealed that things are going strong with Anna Osceola.

“I’m in a relationship right now and … it’s comfortable, it’s a feeling of taking care of someone else and being taken care of,” Jon told Howard.

Jon continued to explain: “It’s only been in the last couple of years, me kind of sitting down and really thinking about all that stuff, that’s made the relationship that I’m in now even more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness … It sounds hokey and whatever, but it’s real and it’s — for want of a better word — it’s what I’m working for.”

When asked by Howard Stern if he is in love, Jon replied: “I very much so am.”

Photo by Emma McIntyre/WireImage,
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Eve spends her days writing about everything culture-related. From celebrity news to music, film and television, Eve covers all bases. When she’s not writing you can find her making music or mastering the art of homemade pasta.