Jon Hamm and fiancee Anna Osceola have NYC date night: pic

Felipe Ramales /

Discover the Big Apple! Jon Hamm and fiancé Anna Osceola Enjoyed a romantic dinner in New York City before doing some shopping.

Mad Man The co-stars kept it casual for their night on the town as they dined at Cipriani restaurant on Tuesday, May 23. Haim, 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 strolled hand-in-hand through the Upper East Side before stopping at Bergdorf Goodman to shop.

Top Gun: Maverick star and The Massachusetts natives first linked in spring 2020 after being seen together on several occasions. us weekly Their romance was confirmed in June of that year after they were photographed playing tennis together in Los Angeles in May 2020. Two years later, she made her red carpet debut in March 2022 while attending the Oscars after-party.

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

“It’s comforting, and it’s a feeling of being taken care of and cared for by someone else,” he said during a September 2022 episode. the howard stern showSaying that he could “definitely” see himself proposing NCIS future actress.

Felipe Ramales /

unbreakable kimmy schmidt The alum shared that “unpacking” his childhood trauma—particularly the death of his mother—allowed him to forge a deeper bond with Osceola.

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

After three years of dating, We A source exclusively revealed, “The engagement took place some time ago, but they are still in cloud nine.” We those days. “They have so much fun together and already feel married.”

before his relationship with law & Order alum, was in a long term relationship with Haim jennifer westfeld 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 former wrote in a joint statement at the time. “We will continue to support each other in every way we can moving forward.”

town The star later spoke about the split during a June 2017 interview with in style, “It’s okay,” he said. “It’s hard. It’s hard being single after being together for a long time. It’s really harsh. It sucks.

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