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Jon Hamm and Fiancee Anna Osceola Have NYC Date Night: Pic

Felipe Ramales /

Exploring the Big Apple! Jon Hamm and fiancée Anna Osceola enjoyed a romantic dinner in New York City before indulging in some shopping.

The Mad Men costars, who dined at Cipriani restaurant on Tuesday, May 23, kept it casual for their night on the town. Hamm, 52, rocked a tan jacket and red baseball cap with his signature round frames. Osceola, 35, looked boho-chic in a black and white striped tank, blue sweater and green cargo pants. The lovebirds walked hand in hand around the Upper East Side before stopping in at Bergdorf Goodman to make a purchase.

The Top Gun: Maverick star and the Massachusetts native were first linked in spring 2020 after being spotted together on multiple occasions. Us Weekly confirmed their romance in June of that year after they were photographed playing tennis together in Los Angeles in May 2020. Two years later, they made their red carpet debut while attending the Oscars afterparty in March 2022.

The couple — who got engaged in winter 2022 — met while filming their AMC drama in 2015. Hamm portrayed main character Don Draper in all seven seasons of the show, while Osceola, for her part, portrayed spiritual retreat receptionist Clementine in the final episode of the series. They later teamed up again for their 2022 film, Confess, Fletch. While promoting the movie, Hamm gave fans a rare glimpse into their private relationship.

“It’s comfortable, and it’s a feeling of taking care of someone else and being taken care of,” he said during a September 2022 episode of The Howard Stern Showadding that he could “for sure” see himself proposing to the NCIS actress in the future.

Felipe Ramales /

The Unbreakable Kimmy Schmidt alum shared that “unpacking” his childhood trauma — particularly his mother’s death — is what allowed him to form a deep bond with Osceola.

“[It’s] made the relationship that I’m in now even more meaningful,” Hamm told host Howard Stern of going to therapy. “And opened up the possibility of things like being married, having kids — you know, defining a new version of happiness, life, wellness. All that stuff that sounds hokey and whatever, but it’s real and, for want of a better word, it’s what I’m working for. What else is there other than that?”

After three years of dating, Us confirmed the twosome were engaged in February 2022. “The engagement happened a while back, but they are still on cloud nine,” a source exclusively told Us at the time. “They have so much fun together and already feel married.”

Prior to his relationship with the Law & Order alum, Hamm was in a long-term relationship with Jennifer Westfeldt for almost two decades from 1997 to 2015.

“With great sadness, we have decided to separate, after 18 years of love and shared history,” the exes wrote in a joint statement at the time. “We will continue to be supportive of each other in every way possible moving forward.”

The Town star later opened up about the split during a June 2017 interview with InStyle. “It’s fine,” he said. “It’s hard. It’s hard to be single after being together for a long time. It’s really hard. It sucks.

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