Jon Hamm, 51, has ‘opened up’ to marriage and kids after therapy, is ‘in love’ with Anna Osceola, 34

Jon Hamm has revealed that he is more open to the idea of marriage and children amid his relationship with Anna Osceola.

The 51-year-old actor – who has never been married before – was candid as he talked about his relationship with the 34-year-old actress and how therapy has helped  him think more seriously about the future of their relationship.

He appeared on The Howard Stern Show on SiriusXM on Monday where he talked about feeling ‘very settled and comfortable’ at this stage in his life with the stunning actress.

Revealing: Jon Hamm revealed on The Howard Stern Show on SiriusXM on Monday that he is more open to the idea of marriage and children amid his relationship with Anna Osceola

Opening up: The 51-year-old actor - who has never been married before - was candid as he talked about his relationship with the 34-year-old actress and how therapy has helped him think more seriously about the future of their relationship, as they are pictured in West Hollywood earlier this month

Opening up: The 51-year-old actor – who has never been married before – was candid as he talked about his relationship with the 34-year-old actress and how therapy has helped him think more seriously about the future of their relationship, as they are pictured in West Hollywood earlier this month

Jon said: ‘I’m in a relationship right now and… it’s comfortable, it’s a feeling of taking care of someone else and being taken care of.’

The Emmy Award winner was open as he revealed that he has been seeking therapy over the past few years and has found that a lot of his trauma comes from losing his mother to colon cancer when he was just 10-years-old.

He said: ‘It’s also been a process of working on myself, my mental health, all the stuff with my therapist. And unpacking all of that trauma and realizing that when you lose someone that’s so important to you, like a mother, so early, that that creates a wound that blocks a lot of that emotional accessibility.

‘That blocks a lot of that availability and vulnerability.’ 

Jon said: 'I'm in a relationship right now and... it's comfortable, it's a feeling of taking care of someone else and being taken care of'

Jon said: ‘I’m in a relationship right now and… it’s comfortable, it’s a feeling of taking care of someone else and being taken care of’

'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': Talking with a therapist has also helped him get in the mental space where he is more open to the idea of taking his relationship with Anna to the next level

‘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’: Talking with a therapist has also helped him get in the mental space where he is more open to the idea of taking his relationship with Anna to the next level

Talking with a therapist has also helped him get in the mental space where he is more open to the idea of taking his relationship with Anna to the next level.

Jon explained: ‘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 want of a better word — it’s what I’m working for.’

Working relationship: Jon and Anna have been romantically linked since 2020 but had first met when she played a receptionist named Clementine on the series of Mad Men, which aired in 2015

Working relationship: Jon and Anna have been romantically linked since 2020 but had first met when she played a receptionist named Clementine on the series of Mad Men, which aired in 2015 

Host Stern, 68, commented that it sounds like Jon is ‘in love’ to which he confidently replied ‘I very much am.’ 

Jon and Anna have been romantically linked since 2020 but had first met when she played a receptionist named Clementine on the series of Mad Men, which aired in 2015.

Romance rumors swirled around them a couple of years ago when they were repeatedly seen running errands together during the coronavirus lockdowns.

Smoldering sensation: They made their red carpet debut earlier this year as they attended the Vanity Fair Oscars after party together back on March 27

Smoldering sensation: They made their red carpet debut earlier this year as they attended the Vanity Fair Oscars after party together back on March 27

They made their red carpet debut earlier this year as they attended the Vanity Fair Oscars after party together back on March 27.

During that same interview Jon finally addressed the rumor that he prefers going commando a decade after pictures of him strutting down Madison Avenue while wearing clingy pants went viral.

The well-endowed star burst out laughing when he was confronted about ‘the whole penis thing.’

The host brought up the New York Daily News’ report in 2013 that Jon ‘was politely instructed by an AMC staffer to please wear underwear’ while shooting Mad Men because his ‘impressive anatomy was too distracting.’

Emmy winner Jon finally addressed the rumor that he prefers going commando a decade after pictures of him strutting down Madison Avenue while wearing clingy pants went viral (pictured in 2012 with ex-girlfriend Jennifer Westfeldt)

Emmy winner Jon finally addressed the rumor that he prefers going commando a decade after pictures of him strutting down Madison Avenue while wearing clingy pants went viral (pictured in 2012 with ex-girlfriend Jennifer Westfeldt)

‘I have worn underwear every single day of my life, Howard,’ Hamm stated.

‘First of all, who doesn’t wear underwear? Yeah, I’ve worn underwear every day of my life. With a suit? Come on. I love a comfy boxer brief, thank you very much. I like a breathable cotton. Who doesn’t?’

The St. Louis native was on Stern to discuss producing and starring as investigative reporter Irwin ‘Fletch’ Fletcher in Confess, Fletch – which reunited him with his Mad Men co-star John Slattery.

And Slattery wasn’t alone as Jon’s Mad Men castmate-turned-girlfriend Anna also has a small role as Larry in Greg Mottola’s critically-acclaimed crime comedy, which premieres October 28 on Showtime.

'This gets into the most famous rumor about you, with the whole penis thing,' Howard Stern said

'The whole penis thing!' Jon repeated, laughing

The well-endowed 51-year-old burst out laughing when he was confronted on The Howard Stern Show on Monday about ‘the whole penis thing’

Just a rumor: The 68-year-old host brought up the New York Daily News' report in 2013 that Jon 'was politely instructed by an AMC staffer to please wear underwear' while shooting Mad Men because his 'impressive anatomy was too distracting'

Just a rumor: The 68-year-old host brought up the New York Daily News’ report in 2013 that Jon ‘was politely instructed by an AMC staffer to please wear underwear’ while shooting Mad Men because his ‘impressive anatomy was too distracting’

Hamm stated: 'I have worn underwear every single day of my life, Howard. First of all, who doesn't wear underwear? Yeah, I've worn underwear every day of my life. With a suit? Come on. I love a comfy boxer brief, thank you very much. I like a breathable cotton. Who doesn't?

Hamm stated: ‘I have worn underwear every single day of my life, Howard. First of all, who doesn’t wear underwear? Yeah, I’ve worn underwear every day of my life. With a suit? Come on. I love a comfy boxer brief, thank you very much. I like a breathable cotton. Who doesn’t?

The St. Louis native was on Stern to discuss producing and starring as investigative reporter Irwin 'Fletch' Fletcher in Confess, Fletch - which reunited him with his Mad Men co-star John Slattery (L)

The St. Louis native was on Stern to discuss producing and starring as investigative reporter Irwin ‘Fletch’ Fletcher in Confess, Fletch – which reunited him with his Mad Men co-star John Slattery (L)

Premieres October 28 on Showtime! And Slattery wasn't alone as Jon's Mad Men castmate-turned-girlfriend Anna (2-R, pictured September 7) has a small role as Larry in Greg Mottola's critically-acclaimed crime comedy

Premieres October 28 on Showtime! And Slattery wasn’t alone as Jon’s Mad Men castmate-turned-girlfriend Anna (2-R, pictured September 7) has a small role as Larry in Greg Mottola’s critically-acclaimed crime comedy

'It blocks a lot of that emotional accessibility': For the past two years, Jon has been in therapy working on himself and the trauma he sustained at age 10 when his mother Deborah died from colon cancer

‘It blocks a lot of that emotional accessibility’: For the past two years, Jon has been in therapy working on himself and the trauma he sustained at age 10 when his mother Deborah died from colon cancer

Marcia Gay Harden, Kyle MacLachlan, Roy Wood Jr., Annie Mumolo, and Lucy Punch also appear in the remake of the eighties Chevy Chase movies – which were based on Gregory Mcdonald’s 1976 novel. 

The two-time Golden Globe winner and Osceola love watching the ‘remarkably entertaining’ Beat Bobby Flay on the Food Network as well as the ‘fascinating’ Bravo show The Real Housewives of Beverly Hills.

Howard asked Jon if he thought Erika Jayne should give back the $750K diamond hoop earrings bought by her estranged second husband Thomas Girardi in 2007 with embezzled funds.

‘Yes! She should. She should,’ Hamm passionately replied.

Who knew he was a fan? The two-time Golden Globe winner and Osceola love watching the 'remarkably entertaining' Beat Bobby Flay on the Food Network as well as the 'fascinating' Bravo show The Real Housewives of Beverly Hills

Who knew he was a fan? The two-time Golden Globe winner and Osceola love watching the ‘remarkably entertaining’ Beat Bobby Flay on the Food Network as well as the ‘fascinating’ Bravo show The Real Housewives of Beverly Hills

'Yes! She should': Howard asked Jon if he thought Erika Jayne (pictured in 2019) should give back the $750K diamond hoop earrings bought by her estranged second husband Thomas Girardi in 2007 with embezzled funds

‘Yes! She should’: Howard asked Jon if he thought Erika Jayne (pictured in 2019) should give back the $750K diamond hoop earrings bought by her estranged second husband Thomas Girardi in 2007 with embezzled funds

Hamm passionately replied: 'The circular argument that she's not responsible, you just want to shake her and go: "Honey, they were never yours. Give them back. Give them back"'

Hamm passionately replied: ‘The circular argument that she’s not responsible, you just want to shake her and go: “Honey, they were never yours. Give them back. Give them back”‘

‘The circular argument that she’s not responsible, you just want to shake her and go: “Honey, they were never yours. Give them back. Give them back.”‘

In June, Judge Barry Russell ordered the 51-year-old socialite to give Estate trustees the earrings, which were paid for with money stolen from the $2M settlement meant for the families of the victims of the fatal 2018 Lion Air plane crash.

The Big Lie producer-star also has upcoming acting gigs in the third season of Apple TV+ series The Morning Show, the fifth season of FX’s Fargo, and the second season of Prime Video’s Good Omens.

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