Anna Osceola Latest Celebrity News & Gossip

CAA is kicking off Oscars weekend with a star-studded-party!

Mad Men co-stars Jon Hamm and Anna Osceola are engaged, according to reports.The pair are believed to have met on the set of Mad Men during the show’s seventh and final season in 2015. In the show, Osceola portrayed Clementine in the show’s finale, who works at a remote wellness retreat Don Draper (Hamm) attends.According to People, the couple, who became romantically linked in 2020, are engaged after two years of dating.

Mad for each other. Not only did Jon Hamm win an Emmy for his role as Don Draper on Mad Men, but the show introduced him to the love of his life, Anna Osceola.

Madly in love! Jon Hamm is engaged to his former Mad Men costar Anna Osceola, Us Weekly can confirm.

Jon Hamm and Anna Osceola are engaged after two years of dating, per . The couple first met on the set of in 2015. Hamm's rep has not responded to a request for comment. Osceola, 34, appeared as a guest in 's final episode. She played a receptionist at the retreat center that Hamm's character, Don Draper, attended.

Jon Hamm and his girlfriend Anna Osceola, who is now officially his fiancé!After two years of dating, the actor and his costar in 2022's Confess, Fletch are engaged, People reports.The two reportedly met back in 2015 while on the set of Mad Men – Anna had a small role in the series finale – though they weren't romantically linked until 2020.WATCH: Jon Hamm stars in Top Gun: MaverickMORE: Jon Hamm makes rare statement about his future with girlfriend Anna OsceolaWhile neither of them have Instagram pages, and Jon has remained largely mum on the subject of his relationship, they have several red carpet appearances together.Still, the actor did open up about his love life in a rare candid interview with Howard Stern back in September of 2022, during which he opened up about having to work through a lot of trauma in order to see himself getting married.MORE: Jennifer Aniston shares cozy set photo with Jon Hamm ahead of birthday celebrations"Could you ever commit to one woman, be married?" the radio show host asked, and he didn't hesitate with his response, insisting: "Yes. I've never been married, but I could for sure." The couple have known each other since Jon's Mad Men daysHe explained: "This is all part of what I'm saying, this is another place in my life that I feel very settled and comfortable with." Then he added: "I'm in a relationship now and it's comfortable, it's a feeling… Taking care of someone else and being taken care of."DISCOVER: Amy Robach and T.J.

It looks like Jon Hamm is off the market!

She’s said to have had a crush on him for years, and pictures of Jennifer Aniston and Jon Hamm filming for the new series of The Morning Show have been just a small indication of the chemistry between the Hollywood legends, leading to speculation that the pair could become more than just co-stars. But it’s bad news for Jen, as we’re told Jon, 51, and his long-term girlfriend and fellow actress Anna Osceola, 34, are engaged.An insider reveals, “Anna is well aware of Jen’s crush – it was one of Hollywood’s worst kept secrets for years, even before Jen signed him up for The Morning Show.”Rumour has it that 53-year-old Jen – who’s an executive producer on the hit Apple TV+ series, as well as its star – wanted Jon to join season three partly because of her crush on the actor.

Getting the new “Fletch” sequel made took some sacrifice.

Jon Hamm has been working with a therapist to "unpack" his trauma. The 51-year-old actor lost his mother to cancer at the age of ten, and Jon admits that he needed to work on his mental health before he was able to truly commit himself to his girlfriend Anna Osceola. The Hollywood star shared: "I'm in a relationship right now and .

Jon Hamm is "very much" in love with his girlfriend Anna Osceola. During an appearance on The Howard Stern Show on Monday, host Howard asked the Mad Men actor whether he was "in love" with his partner. "I, very much so, am," he replied.

Jon Hamm is madly in love with fellow "Mad Men" actress Anna Osceola.  Hamm got candid in an interview about their relationship, and said he’s "very much" head over heels for his partner.  "It's only been in the last couple of years, me kind of sitting down and really thinking about all that stuff, that's made the relationship that I'm in now even more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness..." Hamm said on "The Howard Stern Show" Monday."It sounds hokey and whatever, but it's real and it's – for want of a better word – it's what I'm working for." The "Mad Men" alum’s comments come on the heels of the actor revealing he’s been in the "process of working on [himself]" after losing his mom when he was 10 years old.  In March, Jon Hamm, 51, and Anna Osceola, 34, made their red carpet debut as a couple at an Oscars party. (Getty Images) Hamm added that it took him some time and therapy to get to a state where he could consider settling down with Osceola.  Jon Hamm got candid in an interview about the Hollywood couple’s relationship and said he’s "very much" head over heels for his partner, Anna Osceola.

Jon Hamm is opening up about being in love with his partner Anna Osceola.

Ready to settle down? Jon Hamm gushed about his girlfriend, Anna Osceola, in a new interview — and hinted that the couple are discussing marriage.

Jon Hamm sat down for his first interview on SiriusXM’s “The Howard Stern Show” where he chatted about a number of topics including his current relationship and meeting Tom Cruise for the first time, plus he finally addressed a longstanding rumour about himself.

“Confess, Fletch.”Based on a 1976 novel of the same name by Gregory McDonald (which was turned into a few movies starring Chevy Chase), the latest adaptation follows Fletch as he tries to solve an art theft, before getting involved in a murder investigation as well. The former investigative journalist begrudgingly comes out of retirement to pursue a number of leads, including his girlfriend.If you’re wondering how to watch “Confess, Fletch,” we’ve got the answers to all your questions.The comedy action flick opens in theaters Sept.

Jon Hamm is stepping out for the premiere of his new movie!

TV fans weren’t the only ones who were delighted when it was announced Mad Men actor Jon Hamm was joining series three of The Morning Show. Someone who was particularly excited was “super-fan” Jennifer Aniston, whohas apparently had a monster crush on the actor for over 15 years.A source tells heat, “Jon has always been at the top of Jen’s list of guys she’d date in a heartbeat.

Jon Hamm is running a few errands.

Jennifer Connelly loops her arm with husband Paul Bettany‘s while arriving at the premiere of her new movie, Top Gun: Maverick, on Wednesday (May 4) in San Diego, Calif.

Jon Hamm and his girlfriend Anna Osceola are enjoying some quality time together!

Jon Hamm and Casey Affleck are enjoying a night out together.

Jon Hamm stepped out in style for some of the Oscars' biggest after-parties, and he had a special lady on his arm — his girlfriend, Anna Osceola.The  alum, 51, and Osceola made their red carpet debut as a couple while posing for pics at both the party and the Mercedes-Benz viewing party Sunday night.Hamm looked as dapper as ever in a striped, velvet tuxedo jacket and black pants, while the 33-year-old actress opted for something a bit bolder. Osceola rocked a multi-colored floral and geometric print long-sleeved dress, which featured a thigh-high slit, showing off her black, strappy sandals.The couple is believed to have met in 2015 when Osceola appeared on the final episode of, in which she played a secretary at the retreat Hamm's character, Don Draper, ends up at, but it's unclear when they started dating.While Hamm and Osceola have kept their relationship pretty private, they have been spotted out and about over the last few years.The pair was last seen enjoying some Super Bowl Sunday activities ahead of the big game last month and before that were spotted enjoying their time together while on an Italian vacation in September 2021.Before coupling up with Osceola, Hamm was in a long-term relationship with Jennifer Westfeldt.

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!