Jon Hamm Is Dating Former 'Mad Men' Costar Anna Osceola

Off the market! Jon Hamm and actress Anna Osceola are dating, Us Weekly confirms.

The Mad Men alum, 49, sparked romance rumors with Osceola, 32, earlier this year after being spotted together on multiple occasions amid the coronavirus pandemic.

The Unbreakable Kimmy Schmidt alum, who starred alongside Osceola in the season finale of Mad Men in 2015, was seen playing tennis with the actress in May.

The two wore cloth masks over their mouths and noses as they walked from their car to the court in Los Angeles, in photos published by the Daily Mail on May 22. Hamm wore a hat and green shorts while Osceola donned a white and green tennis dress and visor.

A day later, the couple were photographed picking up food in the Los Feliz area of Los Angeles. Hamm was seen waiting in the car as the Massachusetts native hopped out to get the meal.

A Twitter user shared more photos of the pair on May 23, also from an outing in L.A., which led to one fan identifying Osceola as Hamm’s “girlfriend,” adding, “He keeps her hidden.”

The same month, a Reddit thread speculated that the duo were more than just friends and more fans of the actor commented on his relationship status on fan-appreciation Instagram accounts.

“Anna Osceola and Jon Hamm make a beautiful couple,” one user wrote on a photo of Hamm in March.

The lovebirds were previously spotted together in 2018 playing tennis, according to the Daily Mail, and Extra reported that in 2017 they were seen leaving a coffee shop.

In between the couple’s sightings, Hamm was linked to Ben Affleck‘s ex, Saturday Night Live producer Lindsay Shookus late last year.

“The two sat next to each other and Jon was right next to the aisle,” a source told Us exclusively of the pair’s Broadway outing in September. “They weren’t hiding anything! Lindsay and Jon didn’t show much PDA, but there was definitely some flirtatious banter.”

A few months later, the two were seen having dinner together in New York City.

“It did seem to be romantic between Jon Hamm and Lindsay Shookus,” an insider told Us exclusively in November. “They sat next to each other and would touch each other affectionally throughout the night.”

Shookus, 40, and Hamm, were rumored to be dating in early 2017 as well, but the Baby Driver star’s rep told the New York Post’s Page Six at the time that they “have not dated [and] are not friends, they are acquaintances.”

Hamm previously dated actress Jennifer Westfeldt from 1997 to 2015.

“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,” Hamm and Westfeldt, 50, said in a statement in September 2015.

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