Photo: Momodu Mansaray/WireImageJon Hammis opening up about his relationship with fiancéeAnna Osceola.TheMad Menalum reportedly met the actress while shooting the show’s series finale in 2015, however Hamm, 52, and Osceola, 35,weren’t romantically linkeduntil 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 filmConfess, Fletchin 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 filmMaggie Moore(s).“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.”Emma McIntyre/WireImageBefore dating Osceola, Hamm was in a long-term relationship with Jennifer Westfeldt.The couple split in 2015after 18 years together.Ina previous interviewwithHoward Sternfor an episode ofThe Howard Stern Showin 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.”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.”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 ofPEOPLE.
Photo: Momodu Mansaray/WireImage

Jon Hammis opening up about his relationship with fiancéeAnna Osceola.TheMad Menalum reportedly met the actress while shooting the show’s series finale in 2015, however Hamm, 52, and Osceola, 35,weren’t romantically linkeduntil 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 filmConfess, Fletchin 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 filmMaggie Moore(s).“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.”Emma McIntyre/WireImageBefore dating Osceola, Hamm was in a long-term relationship with Jennifer Westfeldt.The couple split in 2015after 18 years together.Ina previous interviewwithHoward Sternfor an episode ofThe Howard Stern Showin 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.”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.”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 ofPEOPLE.
Jon Hammis opening up about his relationship with fiancéeAnna Osceola.
TheMad Menalum reportedly met the actress while shooting the show’s series finale in 2015, however Hamm, 52, and Osceola, 35,weren’t romantically linkeduntil 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 filmConfess, Fletchin 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 filmMaggie Moore(s).
“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.”
Emma McIntyre/WireImage

Before dating Osceola, Hamm was in a long-term relationship with Jennifer Westfeldt.The couple split in 2015after 18 years together.
Ina previous interviewwithHoward Sternfor an episode ofThe Howard Stern Showin 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.”
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.
”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 ofPEOPLE.
source: people.com