At 52, Jon Hamm finally tied the knot in 2023.
In late June 2023, the Your Friends & Neighbors star married longtime girlfriend Anna Osceaola, who he met back in 2015 while on the set of Mad Men — she had a small role in the series finale — though they weren't romantically linked until 2020.
In fact, their nuptials made for a full circle moment for the couple, as it took place at Anderson Canyon in Big Sur, where Mad Men's iconic finale was filmed.
© Lionel HahnThey tied the knot surrounded by friends and family, including fellow celebrities Billy Crudup, Paul Rudd and Tina Fey, and their walkup song of choice was reportedly the theme to the 1967 James Bond film You Only Live Twice.
The wedding also took place after Jon for years went back and forth on whether he would ever become a married man or not, and after a nearly 20 year relationship with a fellow actress.
© FilmMagicJon's relationship with Jennifer Westfeldt
In 1997, Jon, then just starting his acting career, and Jennifer, best known for co-writing, co-producing, and starring in the 2002 indie film Kissing Jessica Stein — which has a brief appearance from Jon — started dating.
The former couple continued to build their Hollywood careers side by side, and in 2011, starred together in Friends with Kids. They broke up in 2015, and shared in a statement at the time: "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."
© WireImageWhat Jon said about marrying Jennifer
They were of course frequently asked whether they would ever tie the knot, and in 2012, Jon, per People, said: "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."
"I don't have the marriage chip, and neither of us have the greatest examples of marriage in our families. But Jen is the love of my life, and we've already been together four times longer than my parents were married," he also told Parade in 2010.
© GettyJennifer supported Jon through rehab
In 2015, Jon underwent rehab for 30 days to treat his alcohol addiction and battle with depression.
It was around then that rumors first swirled that the two were breaking up, however a rep for the couple told People at the time: "The story that appeared in this week's edition of In Touch magazine is not true," adding: "The only gentleman Jennifer visited regularly in Connecticut was Jon, while he was in rehab. They continue to ask for the public's understanding and sensitivity during this challenging time."
His stance on marriage after the break-up
Speaking with Howard Stern back in September of 2022, Jon discussed having to work through a lot of trauma in order to see himself getting married. "Could you ever commit to one woman, be married?" the radio show host asked, and he didn't hesitate with his response, insisting: "Yes. I've never been married, but I could for sure."
He explained: "This is all part of what I'm saying, this is another place in my life that I feel very settled and comfortable with," then added: "I'm in a relationship now and it's comfortable, it's a feeling… Taking care of someone else and being taken care of."
Detailing the work he had to do on himself and his mental health in order to be open to a relationship, he further shared: "It has also been a process of working on myself, my mental health, all this stuff with my therapist and unpacking all of that trauma," admitting that early trauma blocked a lot of his availability and vulnerability when it came to love.
However, he maintained: "It has made the relationship I'm in now more meaningful, and opened up the possibility of being married, having kids, defining a new version of happiness, life, wellness…"
