Jon Hamm and Anna Osceola get engaged after dating for 2 years; Report MGG

Jon Hamm and Anna Osceola are reportedly engaged.

If a new report by PEOPLE is to be believed, the actors are gearing up to wed each other after dating for two years. The lovebirds reportedly first met on the sets of Mad Men in the year 2015. They were then spotted together several times before being romantically linked for the first time in 2015.

PEOPLE reached out to Jon Hamm’s rep for a comment, however, there has been no response yet.

Jon Hamm and Anna Osceola’s relationship timeline

When Jon Hamm met Anna, he was in a relationship with Jennifer Westfeldt. The former couple then broke up after being together for 18 years.

Rumours about Hamm and Osceola’s romance first started doing the rounds in 2020 when the couple was spotted together multiple times. From stepping out for meals together to playing tennis and spending quality time on the beach – they were photographed on all these occasions. Moreover, they also went on a vacation to Italy in September 2021.

Hamm and Osceola made their red carpet debut in March 2022 at an Oscars afterparty. They also arrived together at a screening of their film Confess, Fletch.

Jon Hamm on his relationship with rumoured fiancé Anna Osceola

In September 2022, Jon Hamm spoke about his relationship with Osceola, 34, at length, when he appeared for an interview with Howard Stern on his show SiriusXM. Hamm shared that he could see himself getting married and having children someday. “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. Adding further, the actor elaborated that he had really started to think about the things that have made his relationship more meaningful and “opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness.”