Jon Hamm reportedly engaged to ‘Confess, Fletch’ co-star Anna Osceola

A man in a tuxedo smiles while hugging a woman wearing a floral dress
Jon Hamm, left, and Anna Osceola arrive at the ESPY Awards on July 20, 2022, at the Dolby Theatre in Los Angeles.
(Jordan Strauss / Invision / Associated Press)

“Mad Men” star Jon Hamm is reportedly engaged to his “Confess, Fletch” co-star Anna Osceola.

People reported Monday that the actors got engaged after two years of dating. Representatives for Hamm and Osceola did not immediately respond Monday to The Times’ requests for confirmation.

Hamm, 51, and Osceola, 34, reportedly met on the set of Matthew Weiner’s critically acclaimed “Mad Men” in 2015 but were not romantically linked until 2020, People reported. The couple made their relationship red-carpet official in March 2022 when they stepped out together for an Academy Awards viewing party and attended Vanity Fair’s Oscars after-party together.

Star Jon Hamm and director Greg Mottola kicked in their own money to buy a few more days of production on their talky comedy ‘Confess, Fletch.’

Sept. 23, 2022


Osceola appeared in the final episode of AMC’s Emmy-winning hit playing Clementine, a receptionist who flirts with Hamm’s infamous ad man Don Draper in the series finale. Her other notable credits include “Law & Order True Crime” and “Greek.”

“This is another place in my life that I feel very settled and comfortable,” Hamm said during a September episode of “The Howard Stern Show.” “I’m in a relationship right now and it’s comfortable. It’s a feeling of taking care of someone else and being taken care of.” The Emmy Award winner said that he was “very much” in love and the relationship “opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness.”

The two co-starred together in last fall’s mystery comedy in which Hamm played the titular detective and she played a character billed as “Larry.” (The comedy, the third installment in the film series originally starring Chevy Chase, also starred “Mad Men” alum John Slattery.)

Hamm, who starred in “Unbreakable Kimmy Schmidt” and “The Division,” was long linked to actor and producer Jennifer Westfeldt, but in September 2015 the former couple announced the end of their 18-year relationship.