Jon Hamm on Life with Fiancée Anna Osceola: ‘You Really Have to Lean on One Another’ (Exclusive)

The 'Maggie Moore(s)' star exclusively tells PEOPLE how the couple navigates life together as actors

Jon Hamm is opening up about his relationship with fiancée Anna Osceola.

The Mad Men alum reportedly met the actress while shooting the show’s series finale in 2015, however Hamm, 52, and Osceola, 35, weren't romantically linked until 2020. Cementing their relationship status was somewhat of a "bumpy road," suggests Hamm.

“I think when you're figuring out relationships, there's a reason that that's a genre unto itself in television and film,” Hamm exclusively tells PEOPLE in this week’s issue. “It's a bumpy road towards relationships, but we do get better at it, I suppose. I mean, I feel like I've figured out some things over the course of my half a century on the planet. So I'm in a pretty good place now. Hopefully I'm learning.”

Hamm and Osceola, who would later appear together in the film Confess, Fletch in 2022, got engaged this February. Being in a relationship with another actor presents its own unique challenges, which the couple handles “day to day," explains Hamm, who currently stars in the film Maggie Moore(s).

Related: Jon Hamm and Anna Osceola Are Engaged After Two Years of Dating

“You're in it, it's your life, and so you wake up and you deal with what comes at you,” he says. “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 for their support and for any kind of advice.”

Related: Who Is Jon Hamm's Fiancée? All About Anna Osceola

Before dating Osceola, Hamm was in a long-term relationship with Jennifer Westfeldt. The couple split in 2015 after 18 years together.

In a previous interview with Howard Stern for an episode of The Howard Stern Show in 2022, Hamm discussed the obstacles he overcame to get to a place where he could think about the future of his relationship with Osceola. That process included working with a therapist on his mental health and “unpacking” the trauma from losing his mother at age 10, a life event the actor said locked away much of his emotional “availability and vulnerability.”

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”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 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 it’s — for what of a better word — it’s what I’m working for.”

Maggie Moore(s) is currently in theaters.

For more on Jon Hamm, pick up the latest issue of PEOPLE.

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