Jon Hamm, 51, and girlfriend Anna Osceola, 34, take their dog on a walk as they spend time together

Jon Hamm, 51, and John Slattery, 59, from Mad Men walk their dogs in The Hamptons

Jon Hamm, 51, and girlfriend Anna Osceola, 34, head out on errand run in The Hamptons

Jon Hamm packs on PDA in a black tuxedo alongside girlfriend Anna Osceola at 2022 ESPYS in LA