Jon Hamm was spotted with girlfriend Anna Osceola as he took a splash in the Mediterranean Sea near Pantelleria, Italy, on August 31. The couple took a dip in the water below the Arco dell'Elefante cove, where they kissed, hugged, and wrapped their arms around each other.
The 50-year-old actor was seen in red swim trunks while his girlfriend wore red bikini bottoms with a green strapless bandeau top. They dived into the sea from a small cliff off the shore.
The pair then relaxed on towels along the rocks and wore sunglasses to protect their eyes from the summer sun. They share a love of bumming on the beach and were formerly seen in the sand in Santa Barbara, California, in September 2020.
Jon Hamm dated actress and screenwriter Jennifer Westfeldt from 1997 to 2015. They released a joint statement after the breakup, promising to remain supportive of each other in the future.
Everything to know about Jon Hamm's girlfriend
Born on April 8, 1998, Jon Hamm's girlfriend, Anna Osceola, was raised in Massachusetts and later shifted to California to pursue her passion for acting. There is an age difference of 17 years between them.
The 32-year-old received her big breakthrough in movies in 2007. She played the role of Charlie in the television film, Not Another High School Show. She then appeared in several other shows like Greek, Rizzoli & Isles, and Law & Order: True Crime.
She appeared in the Mad Men series finale in 2015. Don Draper, played by John Hamm, finds himself in California and briefly encounters the receptionist at a wellness retreat, Clementine, played by Anna Osceola.
Osceola has been seen with Hamm more frequently in the last few months. They were spotted playing tennis together and picking up takeout during the ongoing pandemic.
Some media portals claimed that they were in touch after Anna appeared in Mad Men. An American entertainment channel spotted them having coffee together in 2017.
Anna Osceola has never revealed much about her personal life and does not have an account on any social media platform. Jon Hamm has also been private about his life, and he is not active on social media.