Mad Men Alums Jon Hamm and Anna Osceola Engage

Alums Jon Hamm and Anna Osceola

Following several years of dating, Jon Hamm is reportedly engaged to actress Anna Osceola. They met while working on Mad Men, where Osceola played Clementine – a receptionist at a spiritual retreat that Don Draper checked into.

They kept their relationship quiet until 2020 when rumors started swirling about them being an item. Their affectionate gestures became more public in September 2021 when they were photographed enjoying a romantic vacation together in Italy.

Jon Hamm and Anna Osceola’s Relationship

Hamm and Osceola first met on the set of Mad Men, in which Hamm starred as ad man Don Draper and Osceola played Clementine – a receptionist at a retreat that Draper visits frequently.

Jon Hamm and Anna Osceola are well known for their private lives, rarely speaking about their relationship in interviews or on social media platforms. But recently they’ve been more out in the public with red carpet appearances and European vacations.

They reportedly first met on the set of Mad Men in 2015, and were seen together multiple times before becoming a couple.

Their love story has not been without its share of challenges, but their recent engagement marks the start of a new chapter for them.

Hamm and Westfeldt first met while filming Mad Men in May 2015. At that time, Hamm was still dating his longtime girlfriend Jennifer Westfeldt; however, months later after 18 years together they parted ways.

Jon Hamm and Anna Osceola’s Engagement

After nearly two years of dating, Mad Men alums Jon Hamm and Anna Osceola are engaged. It seems like a natural progression for the couple who has been seen spending quality time together on vacations and attending red carpet events since May 2020 when they first started openly sharing their relationship online.

In a 2022 interview with Howard Stern, Hamm revealed his relationship with Osceola has been an integral part of his life. “It’s comfortable and it gives me the feeling of taking care of someone else,” Hamm said, adding that it “for sure” could lead to marriage.

Five years after Hamm’s departure from long-term girlfriend Jennifer Westfeldt, the pair met on set of Mad Men in 2015 – five years after Hamm had broken up with longtime girlfriend Jennifer Westfeldt. Reports indicate they began seeing each other in real life shortly after meeting on set, and things seemed to take off from there.

Jon Hamm and Anna Osceola’s Red Carpet Debut

Mad Men not only made Jon Hamm a household name, but the AMC drama also introduced him to his now-fiancee Anna Osceola. The former co-stars met on the set of Mad Men’s final episode in 2015 when Osceola played a small role as a receptionist at Don Draper’s retreat.

Last year, Hamm spoke with Howard Stern about his relationship with Osceola, which has lasted two years. He credited her with helping him process the trauma that had affected him as a child and providing him with the drive to become a family man.

Though they have kept their relationship private, they were seen giving some serious PDA while on an Italian vacation in September 2021. A year later, in March 2022, they made their first red carpet appearance together at Mercedes-Benz’s Academy Awards viewing party and Vanity Fair’s annual afterparty.

As expected, Hamm and Osceola looked like they were having a wonderful time on their red carpet debut. Hamm donned a stylish velvet tuxedo while Osceola donned an exquisite floral sequined gown.

Jon Hamm and Anna Osceola’s Romantic Vacation

After dating for several years, Mad Men actor Jon Hamm is engaged to Anna Osceola. The couple has been seen out and about frequently; from playing tennis together to enjoying a romantic beach day.

Anna, 34, first encountered the actor when she guest-starred on his show in 2015 as a receptionist at a retreat where Don Draper ended up. Though they didn’t begin dating until 2020, their connection was evident from the start.

During the COVID-19 pandemic, they were often seen taking walks together and going out for meals together, leading people to speculate that they are more than just friends.

It’s unknown when they started dating, but it is believed they met on the set of Mad Men in 2015. Osceola portrayed Clementine, a receptionist at the retreat where Don Draper ends up. Although she hasn’t spoken about her relationship with Hamm in interviews, he reportedly has been open about his feelings towards her.