After once being dubbed Hollywood's most eligible bachelor, it seems as though Jon Hamm is finally ready to settle down.
Even though Hamm was in a relationship for nearly 20 years with Jennifer Westfeldt, people assumed he wasn't fit for marriage.
Following a candid interview, the actor admitted that he's finally ready to take the next step in his love life and why he's changed his idea about marriage.
Stay tuned while we dive into Jon's journey of following his heart and how meeting the right person made him rethink his choices.
For years, Jon has been compared to his most famous character: Don Draper of 'Mad Men;' a cavalier, womanizing drunk who only cared about his desires and very little else.
Many assumed that a handsome man like Hamm wouldn't want to tie himself down and resist the commitment to monogamy.
However, the actor couldn't be more different from his 'Man Men' character. Well, except when it came to the idea of marriage.
During a very open and honest interview with Howard Stern, Jon confessed why he kept away from the marriage institution and what made him finally change his mind.
As always, it was not a straightforward journey, and Hamm had to account for a wide range of factors to come to this conclusion.
In 2010, while he was still dating Jennifer Westfeldt, Hamm famously declared that he didn't have the "marriage chip."
He added that both he and Westfeldt didn't have the greatest examples of marriage in their families, which is why they were skeptical about exchanging vows.
He explained, "But Jen is the love of my life, and we've already been together four times longer than my parents were married."
Jon and Jennifer had started dating around 1997 after meeting at a mutual friend's birthday party.
They were both struggling actors at the time, and after connecting with each other at the party, they decided to help each other out to prepare for upcoming auditions.
They later reconnected to run lines together and immediately felt a spark ignite between them.
Jennifer recalled, "Jon was so sweet and he worked on these lines with me. I was like, 'God, this guy is so talented…and so handsome!'"
However, both Hamm and Westfeldt were seeing other people at the time and were friends for a long time before they eventually started dating.
Soon, the pair became inseparable, so much so that they never spent more than two weeks apart, even with their busy working schedules.
Jennifer explained, "We've done it even if we just have one afternoon together. And even if we're in the same place, we prioritize making sure we have time and spend time.
Especially now with all the demands on Jon's time and our privacy."
Over their years together, it was clear the couple had the unwavering support of one another.
They even got the chance to work together on film projects too, like 'Ira and Abby' in 2006, and 'Friends With Kids' in 2011.
In 2012, Jon also revealed that he had similar reservations about having children.
The actor explained that with his intense work schedule, he'd avoided the idea of becoming a father.
He confessed, "I'd be a terrible father!"
Unfortunately, around 2015, Jon and Jennifer broke up after almost 20 years together.
The former couple announced their split in a shared statement, "With great sadness, we have decided to separate, after 18 years of love and shared history.
We will continue to be supportive of each other in every way possible moving forward."
Shortly after their breakup, a source close to the pair explained that Jon and Jennifer didn't see eye to eye about starting a family.
They shared, "There's always been a rift."
Perhaps that rift was caused by Jon's negative view on marriage and having children.
It's possible that Jennifer was ready to take the next step in their relationship and start a family, and Jon wasn't ready for that.
During a June 2017 interview, Hamm took a rare moment to open up about his private life, including his relationship status.
He got candid about being single, telling the outlet, "It's hard. It's hard to be single after being together for a long time. It's really hard. It sucks."
After all Hamm's comments about avoiding marriage and starting a family, in 2022, Hamm confessed that not only did his opinions change, but he has been able to tap into his tender side.
During his interview with Stern, Jon was asked whether he could ever see himself committing to "one woman" for the rest of his life
and then subsequently going through the motions of a long-term partnership, marriage, the whole works.
Hamm replied with a solid "yes," adding that he's "settled and comfortable" in his place in life.
Jon also explained that since he started dating his current girlfriend, Anna Osceola, he now admires the feeling of being taken care of as well as caring for someone else.
Anna and Jon first met on the set of Mad Men in 2015 but didn't start dating until 2020.
Since then, they've been spotted grabbing meals together, going on vacations, and playing tennis.
The couple also made their red carpet debut in March 2022 at an Oscars afterparty.
Their relationship seems to be thriving since Hamm is contemplating spending the rest of his life with Osceola.
But it wasn't just Anna that changed his mind about marriage. Jon also took a lot of time to work on his mental health and emotional processing over the years.
He shared, "It's also been a process of working on myself, my mental health, all the stuff with my therapist."
Jon was able to figure out that his stance on marriage was shaped by a traumatic experience during his childhood.
At just ten years old, Hamm lost his mother to cancer.
This terrible tragedy was what led young Jon to experience profound grief and trauma throughout his adolescence.
In fact, the pain was so consuming that it severed his ability to build and nurture connections with others, whether romantic or friendly.
The actor shared, "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."
It wasn't until Jon was in his late forties that he was able to come to terms with the depth of his sadness and take the necessary measures to reclaim some of his "availability and vulnerability."
Therapy played a huge role in helping him bridge some of the gaps.
He took the time to "sit down" and excavate the root of his suffering, getting to the bottom of what exactly held him back from sharing himself with others.
For Jon, the loss of his mother weighed down his relationships, ridding them of any value or emotion.
Thankfully, after much work on himself and being able to finally process the loss of his mother, Hamm was finally able to dig himself out of the dark hole of grief.
He explained, "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."
Jon now feels like he's able to experience the little joys with Anna and has even begun to see a long-term future with her.
He confessed, "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."
When Stern asked if Hamm was in love, he responded, "Very much so."
He went on to say that "unpacking" the trauma of his childhood has helped him become a better partner.
He explained that speaking to a therapist has helped him learn how to be more vulnerable.
If Jon hadn't taken the time to be introspective and take a deeper look into himself and why he felt so negatively towards marriage and commitment,
he wouldn't have been able to find the happiness he now shares with Anna.
Hamm went on to share, "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."
The couple is so comfortable with where they are in their relationship that they also choose to keep their romance as far away from the Hollywood spotlight as possible.
In fact, Both Jon and Anna live their lives off of social media.
The actor opened up about his decision to set boundaries in the industry and retain his own sense of self, saying,
"The point of life is not to put dog ears on yourself and post it online for everyone to see."
Adding that he didn't see the point of it other than "immediate gratification," which is something neither of them is interested in.
For those of you who want to see more of the couple together, the pair have once again appeared on the screen together for the third installment of the Fletch series.
In the 2022 film, Hamm's character becomes involved in an investigation of an art heist. Osceola also appears in the project, playing the role of "Larry."
Not everyone wants to get married and have children, and that's okay. But for some, those opinions can be linked to something a lot deeper.
For Jon, the loss of his mother at such a young age impacted his ability to be vulnerable and open to long-term commitments like getting married and having kids.
We're so happy that he was able to work through his trauma and open himself up to the possibility of marrying the woman he loves and starting a family.
We only with Jon and Anna the best, and who knows, maybe we'll be hearing wedding bells sooner than we think.