Jon Hamm, best known for his iconic role as Don Draper on Mad Men, and actress Anna Osceola have been enjoying their journey as a married couple. The pair first crossed paths on the set of Mad Men in 2015 and began dating in 2020. Their engagement was confirmed in February 2023, and they tied the knot in a beautiful ceremony in Big Sur, California, in June of the same year. This article delves into their relationship, their lives together, and the milestones they’ve shared.
Meeting on the Set of Mad Men
Hamm and Osceola’s love story began on the set of the critically acclaimed series Mad Men. Osceola had a small role in the final episode, playing a receptionist at Esalen, a spiritual retreat in California that Draper’s character attends. Their initial professional encounter eventually blossomed into a romantic relationship five years later, showcasing how their paths serendipitously crossed.
Engaging and Getting Married
The couple’s relationship took a significant step forward in 2020, when they started dating. By February 2023, Hamm and Osceola were engaged, with the news confirmed by PEOPLE. They celebrated their engagement at the Vanity Fair Oscar afterparty, where Osceola debuted her stunning emerald-cut solitaire diamond ring. Their wedding took place on June 24, 2023, at Anderson Canyon in Big Sur, California. The ceremony was attended by close friends and family, including notable guests like Billy Crudup, Paul Rudd, and Tina Fey. Osceola walked down the aisle in a strapless A-line gown, while Hamm looked dapper in a black tuxedo.
Balancing Careers and Personal Life
Both Hamm and Osceola are accomplished actors, which can present unique challenges in their relationship. Hamm has openly discussed the need for mutual support and advice, given the unpredictable nature of their careers. In an interview with PEOPLE, Hamm emphasized the importance of leaning on each other for support and navigating the uncertainties of their profession together.
Celebrating Milestones
Their first year of marriage was filled with memorable moments, though not without a few humorous mishaps. In January 2024, Hamm revealed to Entertainment Tonight that they had forgotten their six-month wedding anniversary due to the busyness of the holiday season. Despite this, he described their married life as “very nice” and full of joy.
A Private Life Away from Social Media
Both Hamm and Osceola prefer to keep their personal lives private, staying off social media. This decision allows them to maintain a sense of normalcy and avoid the pressures of public scrutiny. Hamm has spoken about the importance of setting boundaries and focusing on genuine, meaningful experiences rather than seeking immediate gratification from social media.
Professional Collaborations
Their relationship has also seen them collaborating professionally. In 2022, they appeared together in Confess, Fletch, the third installment of the Fletch series. Hamm played the lead role of Irwin M. Fletcher, a semi-retired journalist, while Osceola took on the role of “Larry.” Their on-screen chemistry mirrored their off-screen relationship, adding depth to their professional endeavors.
Enjoying Life Together
Hamm and Osceola have shared numerous public appearances, marking significant milestones in their relationship. They made their red carpet debut in March 2022 at an Oscars afterparty and have since attended various high-profile events together, including the 2022 ESPY Awards and the LACMA’s 2023 Art + Film Gala. Their presence at these events highlights their strong bond and shared commitment to supporting each other.
A Romantic Honeymoon
Following their wedding, Hamm and Osceola enjoyed a romantic honeymoon on the Spanish island of Mallorca. They were spotted soaking up the sun, with Osceola in a yellow bikini and Hamm in mint-green swim shorts. This picturesque getaway allowed them to relax and savor their new journey as a married couple.
Future Endeavors
Looking ahead, Hamm and Osceola continue to navigate their careers while building a life together. Hamm’s recent film, Maggie Moore(s), premiered at the 2023 Tribeca Film Festival, with Osceola by his side. Their friend and fellow Mad Men costar, John Slattery, expressed his happiness for the couple, wishing them a long and happy marriage.
Conclusion
Jon Hamm and Anna Osceola’s love story is a testament to the power of connection and mutual support. From their first meeting on the set of Mad Men to their private and joyous wedding in Big Sur, their journey together has been filled with memorable moments. As they continue to navigate their careers and personal lives, their commitment to each other remains unwavering, promising a bright and loving future.
