Jon Hamm, 49, & GF Anna Osceola, 32, Rock Swimsuits For Beach Date 4 Mos. After Romance Goes Public

Life’s a beach for Don Draper. ‘Mad Men’s Jon Hamm ditched the suit for some swim trunks while hitting the waters in Santa Barbara with his bikini-clad girlfriend, the beautiful Anna Osceola.

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Image Credit: Clint Brewer Photography / A.I.M / BACKGRID

It may be the first week of Autumn, but it still feels like summer out in California. Jon Hamm, 49, took advantage of these high temps by shedding some layers for a beach trip on Sept. 26. The Mad Men actor opted to go shirtless, bearing his hairy bare chest before going for a swim at a Santa Barbara beach. He was joined by his 32-year-old girlfriend, actress Anna Osceola. The Greek stare wore an emerald green bikini and a sparkly necklace. The duo took in a dip in the ocean before drying off in the warm California sun.

Jon Hamm and Anna Osceola head hit the beach in Santa Barbara on Sept. 26 (Clint Brewer Photography / A.I.M / BACKGRID)

This beach day comes four months after Jon and Anna were first seen together. The two were spotted playing a game of tennis in May, sparking romance rumors. It turns out that this relationship was five years in the making. Anna appeared on the Mad Men series finale in 2015, portraying the receptionist at the retreat Jon’s Don Draper attends in the ultimate episode. The two briefly shared the screen together, but apparently, she left quite an impression on Jon. He and Anna were seen getting coffee together in 2017, but apparently, it was a friendly encounter.

Jon – who split from his longtime partner Jennifer Westfeldt in 2015 and had a brief romance with Lindsay Shookus in 2019 – confirmed this new relationship with Anna with an act of chivalry. The two were seen going grocery shopping together in Los Angeles on Aug. 14. Anna, at the time, was on crutches due to some unspecified injury to her left foot. As she hobbled her way out to the car, Jon did the right thing by opening the door for her and helping his new bae into the vehicle. During this outing, both wore bandannas over their face as precautions against the COVID-19 pandemic.

Jon Hamm attends the Vanity Fair Oscar Party in 2020.

It’s unclear when Jon and Anna started dating. He and Lindsay Shookus were last spotted together in November 2019 at a Saturday Night Live after-party but seemingly went their separate ways after that. It’s possible that Jon and Anna bonded over their shared background. They both hail from Massachusetts, and both have careers in acting. Anna’s resume may not be as long as Jon’s, but she has some noteworthy appearances on Law & Order True Crime, Saving Grace, and on the tv series, Greek, where she played Robin Wylie.

Jon will be seen in the upcoming Top Gun sequel, and he had nothing but praise for his Tom Gun: Maverick co-star, Tom Cruise. “It was a phenomenal experience working with Tom,” Jon said to HollywoodLife in February. “Really, really enjoyed it. He’s such a great guy, and he’s such a wonderful actor. And it has to be very strange to revisit a role after 30 years that kind of defined your career. But I think the way Tom does it is, he finds it exciting, you know? And rejuvenating. I mean, he looks younger than I do in that movie, so that’s pretty cool!”


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