Sterling Cooper Draper Pryce, please hold!
Jon Hamm and Anna Osceola went red-carpet official on Sunday, March 27, attending an Oscars viewing party hosted by Mercedes-Benz together. Later they attended Vanity Fair’s Oscars after-party together.
The pair likely met when Osceola had a small role in the series finale of Mad Men in 2015, around the same time Hamm split from his longtime partner Jennifer Westfeldt. Spoiler alert: In case you forgot, the Mad Men finale, titled “Person to Person,” finds ad exec Don Draper (Hamm) visiting Esalen, the spiritual retreat in Southern California, after becoming fed up with the advertising game. There he meets Clementine (Osceola), an amiable front desk girl with red ribbons braided into her pigtails.
Later, while meditating, Draper envisions the famous (and very real) “I’d Like To Buy the World a Coke” commercial, which features a woman with a similar hairstyle.
In 2017, Hamm and Osceola were seen leaving a coffee shop together, but rumors about their romance began to spread in 2020. In the last year or so, they’ve been spotted together more often, including on a vacation. Since neither have social media, this red-carpet appearance is likely as official a confirmation as we’re going to get.
Robert Smith, Getty
Since the Mad Men episode, Osceola has appeared on a handful of television shows, most notably in a recurring role on The Menendez Murders. Hamm has starred in a number of shows and movies, including a role in the upcoming and long-awaited Top Gun sequel.
Though it’s likely Jon Hamm and Anna Osceola did not connect romantically until years after their Mad Men moment (Hamm was also briefly linked to Jenny Slate and Dakota Johnson in 2017), they would not be the only couple to forge a strong bond because of the series. Alexis Bledel and Vincent Kartheiser married in 2014 after meeting via the show in 2011. And while it’s not romantic, January Jones is still buds with on-screen daughter Kiernan Shipka. Love that for them.
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