Although they didn’t start dating until 2020, Jon Hamm and Anna Osceola met in 2015 on the set of the Mad Men series finale. Osceola played a hippie at a wellness retreat that Don Draper (Hamm) was staying at after the breakdown of his second marriage/whole fucking life. On June 24, Hamm and Osceola wed at the shooting location where they first met. According to “Page Six,” Osceola walked out to the theme to the James Bond film You Only Live Twice. In attendance were Hamm’s “Clubhouse Playhouse” scene partner John Slattery, Paul Rudd, Larry David, Tina Fey, Brooke Shields, and Billy Crudup (who got married to Naomi Watts in New York earlier this month).
Hamm and Osceola weren’t linked romantically until 2020. They made their red-carpet debut at the Vanity Fair Oscars party. News of their engagement broke in February of this year.