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

One year after Jon Hamm and Anna Osceola tied the knot, the Mad Men actor reflected on how he was initially "terrified" to get married and how he now hopes to have children one day.

By Elyse Dupre Jun 20, 2024 5:04 PM
| Updated Jun 20, 2024 8:14 PM
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Watch: Jon Hamm On Life As A Newlywed: “We’re Still Married”

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.

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Mad Men Stars, Then and Now

"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."

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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

Brayden Bowers & Christina Mandrell

The Bachelor Nation couple got their happily ever after, tying the knot on Dec. 12 in a lakeside ceremony. They kept their nuptials on the down-low until January 2025. 

Emily Osment & Jack Anthony

The Hannah Montana alum married the singer-songwriter "four days ago," she revealed during an Oct. 16 appearance on CBS Mornings, with her brother Haley Joel Osment serving as one of the groomsmen.

Jason Duggar & Maddie Grace

The Duggar family officially gained a new member when Jason—the 12th child of Jim Bob Duggar and Michelle Duggartied the knot with Maddie Grace on Oct. 3, one month after announcing their engagement.

Rebel Wilson & Ramona Agruma

The Pitch Perfect alum exchanged vows with the fashion designer an aca-awesome Italian wedding Sept. 29, with their daughter Royce serving as one of the flower girls.

Lana Del Rey & Jeremy Dufrene

Forget being a Brooklyn baby—the "Blue Jeans" singer became a bayou bride when she married the alligator guide at his workplace, the Airboat Tours by Arthur docks in Louisiana, on Sept. 26.

For the swampside ceremony, Lana wore a custom CINQ gown, which she paired with a "something blue" ribbon in her hair.

Torrey DeVitto & Jared LaPine

The Pretty Little Liars alum had a pretty little wedding with the director in September ahead of the birth of their first baby together.

Ben Platt & Noah Galvin

The Pitch Perfect alum got aca-married to the the Real O'Neals alum on Labor Day weekend after four years of dating.

Jana Duggar & Stephen Wissmann

The former 19 Kids and Counting star tied the knot with the musician—one of 13 siblings and a member of The Wissmann Family gospel band—at a 500-guest wedding in Arkansas Aug. 15.

Despite knowing Stephen—whose sister Hannah is married to her brother Jeremiah—for years, Jana kept their romance out of the public eye until her nuptials.

"I haven't always understood what the bigger picture is, but I know that God knows what is best for all of us," she told People, addressing the yearslong speculation surrounding her relationship status. "And so for me, it's getting married later."

Jessica Szohr & Brad Richardson

Spotted: The Gossip Girl alum tying the knot with the former hockey player on Aug. 11 in a boho-chic Arizona ceremony. It was a star-studded affair, with Nina Dobrev serving as the Maid of Honor.

Saoirse Ronan & Jack Lowden

The Mary Queen of Scots costars wed at the Edinburgh Central Registrar’s Office, according to Scottish civil marriages records. Their nuptials reportedly occurred the weekend of July 20.

Jed Wyatt & Ellen Decker

The Bachelor Nation star, who vied for Hannah Brown's heart on 2019 season of The Bachelorette, married the fitness trainer at a Tennessee wedding on July 20.

Jana Kramer & Allan Russell

The One Tree Hill alum and the former soccer player wed in his native Scotland July 13 in front of 35 guests, including their newborn son Roman, as well as Jana's kids Jolie and Jace from her previous marriage to Mike Caussin and Allan's teenage son Troy from a past relationship.

 

Eddie Murphy & Paige Butcher

The Coming to America star wed the model on July 8—five years after after their 2018 engagement—at a private ceremony on the Caribbean island of Anguilla.

John Mulaney & Olivia Munn

The comedian and the Newsroom actress—who welcomed son Malcolm in 2021—tied the knot over the Fourth of July weekend, E! News confirmed.

Chase McNary & Ellie White

The former Bachelorette contestant and the hat designer tied the knot during a Colorado mountain wedding on July 6.

Thomas Brodie-Sangster & Talulah Riley

The Pistol costars tied the knot in June in a ceremony north of London, The Sun reported, less than a year after annoucing their engagement. 

Olivia Culpo & Christian McCaffrey

The former Miss Universe said "I do" to the San Fransisco 49ers player on June 29 at her home state of Rhode Island.

Jodi Balfour & Abbi Jacobson

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.

Hassie Harrison & Ryan Bingham 

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.”

Millie Bobby Brown & Jake Bongiovi

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

Hailie Jade & Evan McClintock

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

Taylor Kinney & Ashley Cruger

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

Sandy Yawn & Leah Shafer

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

Sheri Easterling & Jess Curtis

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

Nick Viall & Natalie Joy

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

Alex Cooper & Matt Kaplan

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.  

Kimberly J. Brown & Daniel Kountz

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

Don Lemon & Tim Malone

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.

Brock Purdy & Jenna Brandt

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.

Shohei Ohtani

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."

His spouse's identity was later revealed to be Mamiko Tanaka, a former professional basketball player.

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