Jon Hamm and Anna Osceola: A Timeline of Their Relationship (2024)

Not only did Jon Hamm win an Emmy for his role as Don Draper on Mad Men, but the show introduced him to his wife, Anna Osceola.The actors met while filming the series finale of the AMC drama in 2015, as Osceola played Clementine, a receptionist at the retreat Hamm’s character attended. Though briefly linked in 2017, Us Weekly confirmed the couple’s romance in June 2020. After nearly three years of dating, Hamm took things to the next level by popping the question to Osceola.Though neither are on social media, they have shared several fun moments over the years, from red carpet appearances to European vacations to sharing the screen again and more. Staying out of the spotlight seemed to do the trick, as the Top Gun: Maverick star admitted that he could “for sure” see himself settling down with Osceola on The Howard Stern Show in September 2022.Hamm and Osceola said "I do" in June 2023 in an outdoor ceremony at Anderson Canyon in Big Sur, California.Before Osceola, Hamm was in an 18-year-long relationship with actress Jennifer Westfeldt. Together since 1997, the pair called it quits in September 2015. A source told Us at the time that although the two “definitely tried” to make things work, there was “always a rift” between them, noting, “He wanted kids and she didn’t.”Hamm opened up about the breakup in a June 2017 interview with InStyle. “It’s fine,” he said, adding, “It’s hard. It’s hard to be single after being together for a long time. It’s really hard. It sucks.”Scroll below to relive Hamm and Osceola’s sweetest relationship moments:

The two first met while filming the season finale of AMC's Mad Men, which aired on May 17, 2015.

The pair were spotted together for the first time off-screen exiting a coffee shop.

Three years later, Hamm and Osceola were spotted in public again, playing tennis together in Los Angeles.

A month later, Us confirmed that the couple were officially dating.

Later that year, the two soaked up the sun while enjoying a day at the beach in Santa Barbara, California.

The stars took their romance abroad and soaked up the sun during their vacation in Italy.

Nearly two years after making their romance official, Hamm and Osceola made their red carpet debut at an Oscars viewing party hosted by Mercedes-Benz, a car brand of which Hamm is an ambassador.

The happy couple made another red carpet appearance at the premiere of Sarah Silverman's musical Bedwetter in New York City.

Hamm opened up about his love life on an episode of The Howard Stern Show, admitting that he and Osceola's relationship felt "comfortable,” telling host Howard Stern, “It’s a feeling of taking care of someone else and being taken care of."

The actor went on to note that working through past trauma with his therapist allowed him to become more vulnerable and emotionally available.

He added: “It’s only been in the last couple of years of me kind of sitting down and really thinking about all that stuff that’s made the relationship that I’m in now, is even more meaningful, and opened up the possibility of being married, having kids, defining a new version of happiness, life, wellness. All that stuff, it sounds hokey and whatever, but it’s real.”

Seven years since sharing the screen on Mad Men, the two appeared alongside each other in the comedy film Confess, Fletch. Hamm starred as the film's titular journalist, Irwin M. Fletcher, while Osceola played a character named Larry.

A source confirmed the pair’s engagement in a statement to Us, revealing, "The engagement happened a while back, but they are still on cloud nine. They have so much fun together and already feel married.”

One month after news broke of their engagement, the twosome stepped out in Hollywood for the Vanity Fair Oscar Party.

The lovebirds said "I do" at an outdoor wedding in Big Sur, California, in front of family and friends, including John Slattery, Paul Rudd and Tina Fey. After their wedding, an insider exclusively told Us that the pair are already considering starting a family. "He and Anna are thinking of having kids soon," the source said. "Jon feels like this is the beginning. He's happy and healthy, and his friends love seeing him like this."

"They've been playing house and enjoying romantic nights in, just the two of them. Jon's gotten so much better about setting work aside or turning down invites with his buddies to enjoy couples time," a source told Us."Everyone's noticed how his wife is his No. 1 priority now, and he seems proud to be putting her on this pedestal."

Hamm and Osceola walked the red carpet together at the SAG Awards at the Shrine Auditorium and Expo Hall in Los Angeles. Hamm's Fargo performance was nominated for Outstanding Performance by a Male Actor in a Miniseries or Television Movie and he was up for Outstanding Performance by an Ensemble in a Drama Series with The Morning Show. He lost both categories.

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