4 Reasons Why Jon Hamm & Anna Osceola's Relationship Will Work (& 2 Reasons Why It Won't)

The following article includes references to mental health struggles and alcohol addiction.

"Mad Men" actor Jon Hamm found love with his fiancée, Anna Osceola, after leaving a long-term relationship with his ex-girlfriend, Jennifer Westfeldt. The super private couple reportedly delayed announcing their engagement and instead waited until they were ready to share the happy news with the world. "The engagement happened a while back, but they are still on cloud nine," an unnamed source told Us Weekly in February 2023. "They have so much fun together and already feel married."

It seems that Hamm and Osceola — who's 17 years his junior — really enjoy their privacy, so that likely leaves fans all the more curious about their love story. We've done some digging and it turns out that the details of this celeb pairing's relationship are quite interesting. However, Hamm and Osceola's histories might make you wonder whether or not they'll survive the challenges of dating in Hollywood. It looks like the duo is off to a good start, but as with any high-profile romance, who knows where their relationship could go?

Here are four reasons why Jon Hamm and Anna Osceola's relationship will work and two reasons why it might not.

It might be safe to assume that Jon Hamm sees a future with Anna Osceola considering the fact that they're engaged. You may think that this is the expected next step for a couple who has been together for over two years, as of this writing, but it turns out that marriage may have not always been a priority for Hamm. He dated his ex-girlfriend, director and actor Jennifer Westfeldt, for 18 years and they never got engaged. Of course, there's a chance that the former couple simply wasn't interested in marriage (more on this below), but it seems he's changed his mind about this in his relationship with Osceola — which is one of many reasons why we feel their relationship will work. 

Hamm spoke about potentially building a future with his new love during a 2022 appearance on "The Howard Stern Show." "It's only been in the last couple years of 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," Hamm explained. "You know, defining a new version of happiness, life, wellness, all that stuff." He added, "It sounds hokey and whatever, but it's real." 

The "Tag" actor went on to confirm that he's in love with Osceola. It looks like this relationship has given Hamm a new outlook on life.

Jon Hamm and Anna Osceola are among the many celebrity couples who stay out of the spotlight — and this pair was most private in the early stages of their relationship. They were first photographed on what appeared to be a coffee date in 2017, though they kept the PDA to a minimum and could have very well just been close friends at the time.

Hamm and Osceola weren't photographed out in public together again until 2020. Either these stars are very good at hiding, or it took a while for their relationship to pick up again. The duo was seen out and about more frequently throughout that year; they were even caught going on a romantic stroll and enjoying a beach date. The celeb pairing took things to the next level in the fall of 2021 when they vacationed in Italy together. Unfortunately for curious fans, these two are so private that they didn't document the trip on social media.

For his part, Hamm has shared why he isn't a fan of social media. "I actually just prefer the act of connection with real people, whether I know them or not," he once told People. "I like talking to people." The actor revealed that he actually does have an Instagram account that he uses for entertainment, but he keeps it secret. It looks like Hamm and Osceola won't be posting selfies to Instagram any time soon, at least not for the consumption of the general public.

You might be wondering how Jon Hamm and Anna Osceola met in the first place. It turns out they first ran into each other on the set of "Mad Men." While Hamm, of course, played the role of the acclaimed show's protagonist, Don Draper, Osceola picked up the role of Clementine in the series. Her character was a receptionist at a retreat. For her part, Osceola has been working in the entertainment industry since 2007. Her first role was in the TV movie "Not Another High School Show," but Osceola has also made appearances in "Rizzoli & Isles," "Law & Order: True Crime," and more.

Hamm and Osceola seemingly don't mind intertwining their careers with their relationship, because they both also took on roles in "Confess, Fletch." The movie is the third film in the series, which began with "Fletch" in 1989. Hamm portrayed journalist Irwin M. Fletcher in the 2022 flick, while Osceola took on the role of Larry. This seemed to be quite the passion project for Hamm, as he reportedly gave up much of his earnings to make the movie possible.

During an interview with Uproxx, director Greg Mottola revealed that it was difficult to find partners for the movie, so he and Hamm pitched in themselves before eventually getting some support from Miramax. "So, basically, what we did is Jon gave back 60 percent of his salary to the budget," he said in part. With this in mind, Osceola's involvement might have been extra special to Hamm.

Jon Hamm has unfortunately endured quite a few tragedies in his life. He lost both of his parents at a young age, which might impact how he navigates relationships. The actor's mom died of colon cancer while he was only 10 years old, and he was 20 when his father died. Hamm's mother and father had gone through a divorce prior to their deaths, which was understandably also difficult for the star to deal with. "[My dad] was twice widowed," the "Mad Men" actor revealed in an interview with Elle. "He was divorced from my mom when she died, but even so, there's a deep sense of tragedy in that. I never had the opportunity to, as an adult, sit down and talk to him about that. It's a real loss."

During his 2022 interview on "The Howard Stern Show," Hamm spoke about experiencing loss at a young age and how it has indeed affected his relationships as an adult. Revealing that he has been able to heal that trauma through therapy, Hamm 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." He added, "It's also been a process of working on myself, my mental health, all this stuff, my therapist, and unpacking all of that trauma and realizing that when you lose somebody that's so important to you — like a mother — so early, that that creates a wound that blocks a lot of that emotional accessibility."

If you or someone you know needs help with mental health, please contact the Crisis Text Line by texting HOME to 741741, call the National Alliance on Mental Illness helpline at 1-800-950-NAMI (6264), or visit the National Institute of Mental Health website.

Now on to the reasons why Jon Hamm and Anna Osceola's relationship might not work: Hamm and ex-girlfriend Jennifer Westfeldt's breakup admittedly could be enough to scare any woman away. The couple began dating in 1997 and later parted ways in 2015. While Hamm and Westfeldt didn't tie the knot during their 18 years together, Hamm previously told the New York Post in 2008, "We may not have a piece of paper that says we're husband and wife, but after 10 years, Jennifer is more than just a girlfriend. What we have is much deeper and we both know that. To me, people [should] get married when they're ready to have kids, which I'm not ruling out."

Marriage isn't the goal for every couple, but Hamm seemingly wasted little time in proposing to Osceola, so what changed? Is there a chance the actor could change his mind about Osceola given he didn't seem interested in marriage before this new relationship? As previously mentioned, Hamm hinted that he's explored the idea of having kids with Osceola while speaking to Howard Stern, but it turns out he previously continued to remain unsure about this, as well. When asked about possibly becoming a dad one day, Hamm told People in 2016 that he enjoyed spending time with his nieces and nephews, but added, "I don't know. I don't think [having kids is] necessarily an imperative."

That said, Hamm has really changed his outlook on relationships and parenthood since then, so let's hope he's confident in his new mindset.

Jon Hamm checked into rehab for alcoholism in 2015. The actor later spoke about his time there during a 2016 interview with Mr. Porter's "The Journal." "It has all these connotations, but it's just an extended period of talking about yourself," Hamm explained. "People go for all sorts of reasons, not all of which are chemically related. But there's something to be said for pulling yourself out of the grind for a period of time and concentrating on recalibrating the system. And it works. It's great." The star also spoke about how he benefitted from therapy. "I find it very helpful," he said. "I know the English are a lot more skeptical about it than Americans are, but maybe after Brexit, you'll change your minds."

It seemed like Hamm's alcohol consumption was a thing of the past until he was photographed drinking again in 2017. He was reportedly enjoying a beer with friends during a night out in Los Angeles. We obviously can't make assumptions about what this means for Hamm's recovery or his engagement with Anna Osceola, if anything — but behavior related to the star's alcohol use allegedly took a toll on his previous relationship with Jennifer Westfeldt. "He has always had demons and needed a mother figure in his life," a source claimed of the actor to People. "It was generally assumed that they would break up once he got sober, because he didn't need to lean on her to take care of him so much."

If you or anyone you know needs help with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).