Anna Osceola Latest Celebrity News & Gossip

Spoiler alert: In case you forgot, the Mad Men finale, titled “Person to Person,” finds ad exec Don Draper (Hamm) visiting Esalen, the spiritual retreat in Southern California, after becoming fed up with the advertising game. There, he meets Clementine (Osceola), an amiable front desk girl with red ribbons braided into her pigtails. Later, while meditating, Draper envisions the famous (and very real) “I'd Like To Buy The World A Coke” commercial, which features a woman with a similar hairstyle. In 2017, Hamm and Osceola were seen leaving a coffee shop together, but rumors about their romance in 2020. In the last year or so, they've been spotted together more often, including on a vacation.

Jon Hamm and Anna Osceola are making their red carpet debut as a couple!

Nothing but love! After working together on the long-awaited Top Gun sequel, Jon Hamm gushed about his “amazing” costar Tom Cruise.

Jon Hamm packed a festive swim trunk for his summer getaway with girlfriend Anna Osceola. The Mad Men actor, 50, wore tropical swim trunks for a day of snorkeling on the Italian island of Pantelleria this week with his actress girlfriend, 33, this week. Anna opted for a multi-colored two-piece bikini as they explored the water, as seen in photos HERE.

Jon Hamm and girlfriend Anna Osceola were spotted sharing some PDA while on vacation in Italy Tuesday. Hamm, 50, showed off his body in red swim trunks while Osceola, 33, donned a green printed bandeau top with mismatched bikini bottom.  The two spent time swimming near Arco dell'Elefante in Pantelleria.

Jon Hamm, 50, kicked off the final weekend of summer with a steamy makeout session with girlfriend Anna Osceola, 33, in Pantelleria, Italy. The lovebirds were photographed sharing a romantic smooch while swimming in the Mediterranean Sea, and each sported swimwear to soak up the sun. Jon was shirtless and wore red swim trunks, while Anna looked super sexy  in a green bikini top and pink bottom. SEE THE PHOTOS HERE.

Jon Hamm and John Slattery are working together again!

Jon Hamm holds out his hand to slow down an approaching car as he and girlfriend Anna Osceola leave their hotel in New York City on Friday (June 18).

Jon Hamm holds on to his dog Splash‘s leash while out on a walk with girlfriend Anna Osceola on Saturday afternoon (March 20) in Los Angeles.

Jon Hamm turned the big 5-0 last week but kept things down to earth.

Jon Hamm turned 50 last week and he’s opening up about what he did for his birthday!

Jon Hamm and Anna Osceola were in the best place possible on Sunday night!

Jon Hamm, 50, showed off his natural grey locks during an outing on Mar. 12 and we’re loving it! The actor, who just celebrated his birthday on Mar.

Jon Hamm walks side by side with girlfriend Anna Osceola as they run a bunch of errands together in Los Angeles on Friday afternoon (March 12).

Jon Hamm and girlfriend Anna Osceola are getting in some fresh air!

Jon Hamm is taking extra precautions for his trip out in public.

Jon Hamm shows off his strength as he picks up a bag of dog food and takes it out to his car in Los Angeles on Friday (December 4).

Jon Hamm and girlfriend Anna Osceola are enjoying some fresh air!

Jon Hamm is joined by longtime girlfriend Anna Osceola while leaving the private members club San Vicente Bungalows after a dinner date on Friday night (November 20) in West Hollywood, Calif.

Jon Hamm and Anna Osceola are making a snack run!

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.

Jon Hamm and his girlfriend Anna Osceola spend the day at the beach together on Saturday (September 26) in Santa Barbara, Calif.

Jon Hamm, 49, stepped out with his new gal pal Anna Osceola, 32, when visiting a butcher shop in Los Angeles, CA on Aug. 14 and showed off his gentleman-like ways when he opened a car door for her. The actor was wearing a blue graphic T-shirt and black shorts during the outing while Anna wore a blue tank top and denim shorts. The new couple also both wore bandannas over their noses and mouths to serve as face masks in the midst of the COVID-19 pandemic.

Jon Hamm pushes the shopping cart back to his car after a trip to Gelson’s Market on Friday (August 14) in Los Feliz, Calif.

Jon Hamm is dating a former Mad Men co-star!

One of the most eligible bachelors in Hollywood is off the market. After four years of single status, Mad Men star Jon Hamm is reportedly in a relationship with his former co-star Anna Osceola.

Anna Osceola is the new woman in Jon Hamm‘s life! Five years after she appeared on the series finale of the Emmy-winning AMC show, Mad Men, which Jon led for its seven-season run, a new report suggests that the two co-stars have grown to be so much more. They were recently spotted playing a game of tennis in Los Feliz, CA in May, but their romance could go back even further! Here are five things to know about Anna Osceola.

Hollywood heartthrob Jon Hamm, who is equally popular in movies and television for his acting stint, has also been in news for his personal life apart from his professional life. The actor made headlines following reports of his alleged relationship with his 'Mad Men' co-star, Anna Osceola.

Jon Hamm reportedly has a new woman in his life! The 49-year-old actor is dating Anna Osceola, 32, according to Us Weekly. The mag’s confirmation of this hot new romance comes after the stars were photographed playing tennis together in May. Anna was a guest star on the season finale of Mad Men in 2015, so she briefly shared the screen with Jon on the hit AMC show.

Jon Hamm and actress Anna Osceola are dating, Us Weekly confirms.The Mad Men alum, 49, sparked romance rumors with Osceola, 32, earlier this year after being spotted together on multiple occasions amid the coronavirus pandemic.The Unbreakable Kimmy Schmidt alum, who starred alongside Osceola in the season finale of Mad Men in 2015, was seen playing tennis with the actress in May.The two wore cloth masks over their mouths and noses as they walked from their car to the court in Los Angeles, in