Jon Hamm Opens Up About Engagement To Anna Osceola

The 52-year-old actor lost his parents when he was young and said his “road towards relationships” has been hard — but he’s finally in “a pretty good place”.

Jon Hamm, who got engaged in February, is finally in “a pretty good place”.

While the 52-year-old Mad Men star met Anna Osceola while shooting the show’s finale in 2015, they were only first linked romantically in 2020. Hamm said finding the right partner wasn’t easy, but that his 35-year-old fiancée is one he can finally “lean on”.

“I think when you’re figuring out relationships, there’s a reason that that’s a genre unto itself in television and film,” he told People in an interview published Wednesday. “It’s a bumpy road towards relationships, but we do get better at it, I suppose.”

Osceola, a fellow actor, most recently starred opposite Hamm in the 2022 detective comedy, Confess, Fletch. Hamm previously dated Jennifer Westfeldt, but notably split with her after 18 years in 2015 — the year he met Osceola.

“I feel like I’ve figured out some things over the course of my half a century on the planet,” he said. “So I’m in a pretty good place now. Hopefully I’m learning.”

Hamm, whose parents divorced when he was two years old, didn’t have it easy. He lost his mother to colon cancer when he was 10, and later his father died when he was 20. Hamm found solace in acting at college, and revealed in 2017 he finally started going to therapy.

Jon Hamm and Anna Osceola first met while shooting the “Mad Men” series finale in 2015.
Jon Hamm and Anna Osceola first met while shooting the “Mad Men” series finale in 2015.
Evan Agostini/Invision/Associated Press

“It’s only been in the last couple of years, me kind of sitting down and really thinking about all that stuff, that’s made the relationship that I’m in now even more meaningful,” he told Howard Stern in 2022, adding he was open to “being married, having kids…happiness”.

While still challenging, Hamm finds life easier and more rewarding with Osceola by his side.

“You’re in it, it’s your life, and so you wake up and you deal with what comes at you,” he told People. “That’s certainly the case with us. The funny thing about this career is that there’s no rule book. You really have to lean on one another and...any kind of advice.”

The trauma of losing one parent as a child and the other soon after oddly made Hamm the best candidate for his fractured Mad Men character of Don Draper. Hamm, who previously revealed he regularly abused alcohol in the past, is fortunately much happier today.

Living with another actor, meanwhile, has shown to be uniquely challenging on its own. Hamm said that he and Osceola handle those hurdles “day to day”, specially when the lines between work and home life appear too blurry to distinguish.

They currently star together in Maggie Moore(s) directed by Mad Men alum John Slattery.


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