Why Jon Hamm Was "Terrified" to Propose to Wife Anna Osceola

Jon Hamm wasn't always madly in love with the idea of marriage.

"I didn't look at marriage as a thing," the Mad Men star explained to The Hollywood Reporter in an interview published June 19. "Obviously, my parents were not married long, so I don't have a model to look at and go, 'Oh, this is how one finds happiness.'"

However, everything changed when he met his now-wife Anna Osceola, whom he acted alongside in the 2015 series finale. Though, Hamm admits popping the question still wasn't easy for him. 

"I just knew at a certain point I wanted to be with this person," he continued. "But when I proposed, I was terrified. I was like, 'What am I doing?' 

While Hamm recalled feeling like taking this step was "really scary," he ultimately figured, "'Well, it probably means it's worthwhile."

And The Morning Show actor is glad he made the leap—in a place that's near and dear to their hearts no less.

"My wedding day was perfect," he added. "Everybody I love was there. It was so emotional, and it felt right. I was like, 'OK, I guess this is a thing.' We did it [where they had shot the Mad Men finale], which was also amazing. Again, it was like a reset, a reboot, a reframe, a reimagining, nine years later, almost to the day. So, it's been great."

And when it comes to his life with Osceola, Hamm sees them one day expanding their family.

"I hope it turns into kids," he told The Hollywood Reporter. "It's not lost on me that I'm 53. I will be the old dad, but so it goes. It could be a good thing. We'll see."

Hamm—who was previously in a relationship with Jennifer Westfeldt for 18 years until their 2015 breakup—and Osceola, 36, tied the knot in June 2023. And while the Confess, Fletch costars have kept much of their relationship private, fans have gotten a few glimpses into their romance, including their honeymoon in Mallorca and date night at the 2024 SAG Awards.

"It's exciting because, again, it's all potential, it's all possibility and it's all positive," Hamm told the Table for Two podcast about marrying Osceola, with the episode being recorded shortly before the wedding. "I suppose there's two ways to look at anything like that—which is, 'Ugh! What if it's terrible?'"

"But the other way is like, 'This is meant to be something wonderful,'" he continued. "And so if you lean into that aspect of it—which I have been, and it's the reason I really wanted to do it and really leaned into it—it's like, ‘This is the thing that leads to the next thing of life.' And that's what I hope it will be."

While Hamm and Osceola are still basking in their honeymoon glow, many other celebrities have since joined the ranks of newlyweds. To see stars who got married this year, keep reading

The Ted Lasso alum married the Broad City co-creator at the Public Records restaurant and music venue in Brooklyn, New York, Cultured magazine reported June 5.

The former Yellowstone actors announced in May 2024 that they'd exchanged vows after a year of dating—as Hassie noted to Vogue, "It’s true what they say—when you know, you just know.”

The Stranger Things actress and the son of singer Jon Bon Jovi said "I do" during a private May ceremony, multiple outlets reported.

The couple tied the knot in an intimate ceremony in May 2024, which came a little over a year after they announced their engagement.

The Chicago Fire star tied the knot with the model in a private ceremony in Chicago on April 30 after two years together.

The Below Deck Captain married her fiancée after five years of dating in a May 11 ceremony which, naturally, took place on a yacht. 

Addison Rae's mom announced on May 11 that she and the high school football coach have been married, "One whole week today."

The Bachelor alum and his girlfriend of about four years got married on April 27 in an elegant wedding ceremony on a Georgia farm owned by Natalie's family. The nuptials arrived two months after the couple welcomed their first child together, a daughter named River Rose Viall. 

The Call Her Daddy host and the film producer tied the knot in an intimate Mexico ceremony on April 4 after four years of dating.  

The Halloweentown II costars married on April 19, 2024, several years after reconnecting.

The former CNN anchor married the real estate broker at a church in New York City April 6, five years to the day they got engaged and on Tim's 40th birthday.

The San Francisco 49ers quarterback married his partner in Des Moines, Iowa March 9, almost a month after his team faced off against the Kansas City Chiefs in the 2024 Super Bowl.

The Los Angeles Dodgers pitcher, who previously made headlines for his $700 million contract with the team, announced in February that he quietly got married. While he didn't name his wife, he did say she was someone "who is very special to me."

The actor kicked off a new chapter in his life with a big bang, sharing in February that he and his now-wife Morgan privately got married and welcomed a baby girl.

Mr. & Mrs. Glover, no Smith here: In early February, the Atlanta star revealed he privately tied the knot with his longtime partner Michelle.

The American Idol alum and her now-husband tied the knot during a celebration in downtown Nashville on Feb. 4.

The Full House alum announced her son Lev and his now-wife Elliot tied the knot at the end of January.

The couple officially kicked off the new year as newlyweds, tying the knot during the Golden Wedding, which aired Jan. 4. The duo announced their separation just a few months later in April 2024. 

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