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

Tom Cruise Sends This Cake to Celebrity Friends Every Year: Miles Teller, Jon Hamm, Angela Bassett & More

Jon Hamm Spends His Afternoon Grocery Shopping in L.A.