Jon Hamm Plays Tennis with Anna Osceola, His Longtime Rumored Girlfriend

Jon Hamm heads to the tennis courts with Anna Osceola to play a game of one-on-one on Friday afternoon (May 22) in Los Feliz, Calif.

The 49-year-old actor has been spotted with Anna, 32, many times over the past three years though they’ve kept their relationship under wraps this whole time. After their friendly game of tennis, they were seen sharing a cute handshake.

Fans have been talking about Jon and Anna being a possible couple for quite some time and now it seems likely that they’re quarantining together. The two actors were also seen getting takeout food together on March 21.

Anna is an actress who guest starred on the series finale of Jon‘s show Mad Men. She played the role of Clementine and had a scene alongside Jon. Most recently, she was seen on the limited series Law & Order True Crime.

The first photos we have of Jon and Anna together date all the way back to January 2017, when they were spotted together at the gym. They were also spotted together at the tennis courts in March 2018. Reddit users spotted the pair at a basketball game in June 2019.

75+ pictures inside of Jon Hamm playing tennis with Anna Osceola

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