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Jon Hamm Dating Anna Osceola; Both Appeared On 'Mad Men'

Home / Stars / Jon Hamm Dating Anna Osceola; Both Appeared On 'Mad Men'

By TheBlast Staff on June 24, 2020 at 10:46 AM EDT

Gettyimages | Rodin Eckenroth

Actor Jon Hammappears to be officially dating Anna Osceola, four years after his breakup with Jennifer Westfeldt. Us Weekly is reporting the news.

They've both been seen together previously this year, wearing face masks, as they should, since the coronavirus is far from over.

Hamm, who was one of the stars of "Mad Men," and Osceola both appeared in the season finale of the show in 2015.

"The Daily Mail" reports that they were seen together back in May, getting ready to play tennis in Los Feliz, California.

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Reddit

Rumors of their romance grew that month as noted by a Reddit thread, where one person wrote: “Anna Osceola and Jon Hamm make a beautiful couple."

In the "Mad Men" season finale, Osceola played the receptionist at a retreat Hamm's character visited.

The two were seen together as far back as 2018 playing tennis, so that seems like a pastime they both like to share.

There was another sighting in 2017 after they were leaving a coffee shop, according to Extra.

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Gettyimages | Gotham

It wasn't that long ago that Hamm was linked with Lindsay Shookus, who had been dating Ben Affleck before that.

Hamm and Shookus were seen out together attending the opening night of the Broadway show "Derren Brown: Secret" in September, and both attended an SNL afterparty together, though Extra notes that they spent time together after the show, but left separately.

"It very much felt like they were on a date. When they were talking to one another, they locked eyes and were smiling the whole time," People wrote.

According to Us Weekly, Shookus and Hamm seemed pretty close.

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“The two sat next to each other and Jon was right next to the aisle. They weren’t hiding anything! Lindsay and Jon didn’t show much PDA, but there was definitely some flirtatious banter. Lindsay turned her head to talk to Jon before the show, during intermission and after the show. She was always smiling and looked like she was enjoying her conversations with Jon.”

They were also allegedly dating in 2017, though a source said they were just "acquaintances."

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Wikimedia | https://commons.wikimedia.org/wiki/File:Jon_Hamm_(8286811119).jpg

From 1997 to 2015, Hamm dated Jennifer Westfeldt. When they broke up it seemed like a much more serious event.

They put out a joint statement in 2015 about their split, saying:

“With great sadness, we have decided to separate, after 18 years of love and shared history. We will continue to be supportive of each other in every way possible moving forward."

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