Anna Osceola Latest Celebrity News & Gossip

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

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.