Latest News

Jon Hamm And Anna Osceola Are Engaged

The couple have taken the next step after two years of dating.
Loading the player...

Jon Hamm and Anna Osceola are reportedly engaged, taking things to the next step after two years of dating.

Although neither party’s reps have confirmed the report, People says they’ve decided to tie the knot.

The notoriously private couple reportedly met on the set of the ACM series Mad Men in 2015, while Hamm, 51, was still in a long-term relationship with his girlfriend of 18 years, Jennifer Westfeldt. Hamm of course starred as ad man Don Draper, while Osceloa made an appearance in the show’s final episode, as a receptionist at a retreat attended by Draper.

Hamm and Westfeldt called it quits a few months later, but it wasn’t until 2017 that Hamm and Osceola, 34, sparked dating rumours when they were photographed together. Those rumours reached a new height in 2020 when they were photographed together multiple times, and travelled to Italy together in 2021.

The couple joined forces for the 2022 film Confess, Fletch, in which Hamm plays the leading role of Fletch and Osceala plays a supporting character called Larry.  

The pair made their long-awaited red carpet debut in March 2022 for an Oscar’s afterparty and have since appeared a multiple other awards season events. 

Jon Hamm Anna Osceola
Jon Hamm and Anna Osceola (Credit: Getty)

Hamm opened up about his relationship with Osceola during a conversation with Howard Stern on the SiriusXM show in September 2022. 

“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,” Hamm said before adding that he was “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?” Hamm told Stern.

While we haven’t gotten a glimpse of the ring yet, we’re looking forward to hearing more about the couple’s upcoming nuptials. 

Related stories