Jon Hamm Just Got Engaged To One Of His Incredibly Beautiful Co-Stars

Jon Hamm and his Confess, Fletch co-star Anna Osceola are engaged.

By Sean Thiessen | Updated

jon hamm Anna Osceola
Anna Osceola and Jon Hamm

Wedding bells are ringing for Mad Men actor Jon Hamm and his fiancé, Anna Osceola. As reported by Entertainment Weekly, the Confess, Fletch stars are now engaged after two years of dating. The remarkably good-looking couple met on the set of Mad Men during the show’s final season.

Anna Osceola played Clementine, the receptionist at a spiritual retreat attended by Jon Hamm’s Don Draper in the series finale of Mad Men. The pair started dating five years later in 2020. Since then, Jon Hamm said he has made significant progress in his mental health and emotional availability.

In an interview with Howard Stern, Jon Hamm opened up about struggles he has faced, including losing his mother when he was just a child. The actor said that therapy and hard work have helped him process that trauma and come to a place where he is ready to redefine success and happiness with love and a family. “It sounds hokey and whatever,” Hamm admitted, “but it’s real and it’s what I’m working for.”

Anna Osceola has mostly appeared in supporting roles on shows like NCIS, Law & Order: SVU, and Bull. She appeared next to Jon Hamm in a small role in Confess, Fletch, a fresh take on the book series by Gregory Mcdonald. Hamm played the role of Fletch, a witty investigative journalist portrayed by Vacation star Chevy Chase in the 1980s.

While Jon Hamm prepares for his new role as a husband and family man, he is also preparing to hit the big screen again. Hamm will appear next in the film Maggie Moore(s), a crime mystery about a small, desert town police chief who must confront the murders of two women who share the same name. Expected this May, the film reunites Hamm with co-star Tina Fey and is directed by Hamm’s Mad Men collaborator John Slattery.

Jon Hamm will also star in the film Off Season, a mystery thriller from writer/director Jonathan van Tulleken about a teen uncovering dark secrets while on a search for his father. Greg Mottola, the director and screenwriter behind Confess, Fletch has hinted that he is at work on a sequel, Fletch’s Fortune, though the film has not yet been greenlit. 

Tina Fey Jon Hamm
Confess, Fletch

Confess, Fletch was a sort of passion project from Mottola and Jon Hamm. The star of the film reportedly gave up 60 percent of his salary to the production in order to complete the project. The movie received a limited theatrical release before it premiered on Showtime; its box office earnings were low as the film had next to no marketing.

Still, those that saw Confess, Fletch generally liked it. On the review aggregate Rotten Tomatoes, the film boasts an 86 percent critics rating and 75 percent audience score. Whether audiences see Jon Hamm and Anna Osceola return in a sequel is up to the powers that be, but a follow-up is on the way if Greg Mottola has anything to say about it.

Beyond that, Hamm may have his hands full with other obligations. The 51-year-old actor is ready to settle down into family life, much to the disappointment of his many admirers across the world. Regardless of how marriage affects his career, there is still more Jon Hamm handsomeness on the way to grace the big screen soon.