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

Felipe Ramales /

Exploring the Massive Apple! Jon Hamm and fiancée Anna Osceola loved a romantic dinner in New York Metropolis earlier than indulging in some purchasing. 

The Mad Males costars, who dined at Cipriani restaurant on Tuesday, Could 23, stored it informal for his or her night time in town. Hamm, 52, rocked a tan jacket and crimson baseball cap along with his signature spherical frames. Osceola, 35, seemed boho-chic in a black and white striped tank, blue sweater and inexperienced cargo pants. The lovebirds walked hand in hand across the Higher East Aspect earlier than stopping in at Bergdorf Goodman to make a purchase order. 

The High Gun: Maverick star and the Massachusetts native have been first linked in spring 2020 after being noticed collectively on a number of events. Us Weekly confirmed their romance in June of that 12 months after they have been photographed enjoying tennis collectively in Los Angeles in Could 2020. Two years later, they made their crimson carpet debut whereas attending the Oscars afterparty in March 2022. 

The couple — who acquired engaged in winter 2022 — met whereas filming their AMC drama in 2015. Hamm portrayed essential character Don Draper in all seven seasons of the present, whereas Osceola, for her half, portrayed non secular retreat receptionist Clementine within the closing episode of the sequenceThey later teamed up once more for his or her 2022 movie, Confess, Fletch. Whereas selling the film, Hamm gave followers a uncommon glimpse into their non-public relationship. 

“It’s snug, and it’s a sense of caring for another person and being taken care of,” he mentioned throughout a September 2022 episode of The Howard Stern Present, including that he might “for positive” see himself proposing to the NCIS actress sooner or later. 

Felipe Ramales /

The Unbreakable Kimmy Schmidt alum shared that “unpacking” his childhood trauma — notably his mom’s loss of life — is what allowed him to type a deep bond with Osceola.

“[It’s] made the connection that I’m in now much more significant,” Hamm advised host Howard Stern of going to remedy. “And opened up the potential of issues like being married, having youngsters — you realize, defining a brand new model of happiness, life, wellness. All that stuff that sounds hokey and no matter, but it surely’s actual and, for need of a greater phrase, it’s what I’m working for. What else is there apart from that?”

After three years of courting, Us confirmed the twosome have been engaged in February 2022. “The engagement occurred some time again, however they’re nonetheless on cloud 9,” a supply completely advised Us on the time. “They’ve a lot enjoyable collectively and already really feel married.”

Previous to his relationship with the Regulation & Order alum, Hamm was in a long-term relationship with Jennifer Westfeldt for nearly 20 years from 1997 to 2015. 

“With nice unhappiness, we’ve got determined to separate, after 18 years of affection and shared historical past,” the exes wrote in a joint assertion on the time. “We are going to proceed to be supportive of one another in each approach potential shifting ahead.”

The City star later opened up concerning the break up throughout a June 2017 interview with InStyle. “It’s nice,” he mentioned. “It’s arduous. It’s arduous to be single after being collectively for a very long time. It’s actually arduous. It sucks.