Jon Hamm and Anna Osceola.Photo: Chelsea Lauren/Shutterstock
Jon HammandAnna Osceolaare engaged!
TheConfess, Fletchcostars are set to wed after two years of dating, PEOPLE confirms. The pair first reportedly met on the set of the AMC seriesMad Menin 2015, before beingspotted together on several occasionsand romantically linked in 2020.
Hamm’s rep has not commented.
Jon Hamm and Anna Osceola.Timothy Norris/FilmMagic
Osceola, 34, appeared in the series' final episode, where she had a small role playing the receptionist at Esalen, a spiritual California retreat that Hamm’s character (Don Draper) attended. At the time, Hamm, 51, was in a long-term relationship with Jennifer Westfeldt. The couplesplitmonths later after 18 years together.
Hamm and Osceola, who both keep off social media, were photographed together once in 2017; romance rumors took off in 2020 when they were seen out multiple times. Since then, they’ve been spotted stepping out for meals, playing tennis andenjoying a day at the beach. They alsotook a vacation to Italytogether in September 2021.
Never miss a story — sign up forPEOPLE’s free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer, from juicy celebrity news to compelling human interest stories.
In March 2022, theymade their red carpet debutat an Oscars afterparty, before stepping out yet again at thered carpet for the Sarah Silverman musicalBedwetterin May, appearing at the 2022 ESPY Awards in July and showing up to a screening for their movieConfess, Fletchjust two months later.
Hammdiscussed his relationship with Osceolain a September 2022 interview withHoward Sternon his SiriusXM show, when he revealed that he could see himself being married some day.
“This is all part of what I’m saying. This is another place in my life that I feel very settled and comfortable. I’m in a relationship right now and it’s comfortable,” he said, later adding that he’s been able to sit down to start “really thinking about all that stuff, that’s made the relationship that I’m in now even more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness.”
“It sounds hokey and whatever, but it’s real and for one of a better word, it’s what I’m working for. What else is there other than that?” he added before confirming that he is “very much so” in love.
source: people.com
