Jon Hamm and Anna Osceola’s Relationship Timeline: From ‘Mad Men’ to Their Engagement and More

EXCLUSIVE: Nick and Jon Hamm’s Free Turn Entertainment has appointed streaming industry veteran Ron Downey as its Chairman.

The perfect match. Hugh Grant has offered rare glimpses at his marriage to Anna Eberstein over the years.

Jon Hamm is looking sharp!

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

EXCLUSIVE: Fox is moving forward with The Flintstones spinoff series Bedrock.

J. Kim Murphy We’ll be right back. “The Eric Andre Show” has set a date for its long-awaited return to Adult Swim. The network announced Tuesday morning that Season 6 of the nightmarish talk show series will premiere on June 4 at midnight. “Eric is back behind the desk like never before; ripped, shredded, full of energy, complete with beads of sweat dripping down from his taut nips onto his glistening six pack abs,” reads Adult Swim’s announcement. “Watch pampered celebrities regret their choices, rappers get the runaround and a slate of street pranks so egregious they collectively inspired a record 30 phone calls to 911.” Billed as “sexy season six,” the series will welcome guests such as Natasha Lyonne, Jaleel White, Blac Chyna, Jon Hamm, Raven-Symoné, Diplo, Daymond John, Meagan Good, Rico Nasty, Waka Flocka Flame, Tinashe, Cypress Hill and Lil Yachty. The network also states that the season will also feature “a host of other celebrities so big we legally can’t use them in promotions.”

Adult Swim will release Season 6 of The Eric Andre Show on Sunday, June 4 at Midnight ET/PT.

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.

EXCLUSIVE: Krapopolis has scored a third season renewal before a frame of the animated series has been seen by the viewing public.

Jon Hamm and Anna Osceola are reportedly set to tie the knot after two years of dating.

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

Talk to me, Goose.

Jon Hamm is going to be a husband! The 51-year-old actor is engaged to Anna Osceola after two years of dating, reports. ET has reached out to Hamm and Osceola's reps for comment.Hamm and Osceola, 34, have largely stayed mum about their romance since the beginning. 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 where Hamm's character, Don Draper, ends up. Hamm split from Jennifer Westfeldt in 2015 after 18 years together.

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!

EXCLUSIVE: UTA has signed actress Richa Moorjani in all areas.

Man of mystery! Michael Cera has kept his private life out of the limelight since he broke into Hollywood in 1999 — and his relationship with wife Nadine is no exception.

is the Emmy-winning drama series about the cutthroat world of television news starring Jennifer Aniston and Reese Witherspoon as two anchors in the middle of the drama that's unfolding on and off-screen at the fictional network UBA. After a twist-filled second season that saw the series adjusting to and incorporating the ongoing health scare and social uprisings that unfolded at the start of the coronavirus pandemic, Apple TV+ renewed it for season 3. As anticipation builds for its return to the streaming platform, with fans dying to know what comes next for Alex (Aniston) and Bradley (Witherspoon), the series has been busy filming on location in New York City and padding it's already star-studded ensemble with even bigger names, like Jon Hamm.

Kate Hudson and her famous mom Goldie Hawn share a striking resemblance, and on Wednesday the Fool's Gold actress proved that the apple really doesn't fall far from the tree!Making a bold entrance at the Michael Kors fashion show, Kate, 43, turned heads in a figure-hugging black ensemble.WATCH: Kate Hudson's new family video has fans asking the same thingThe star looked ultra-glam in her stylish two-piece which featured a bikini-inspired halter neck top and a ruched maxi skirt boasting a daring thigh-high split.Embracing the blazer trend, Kate finished off her look with an oversized jacket which she effortlessly styled over her shoulders. The actress looked sublimeFor the glitzy occasion, the blonde beauty took a leaf out of her mom's book and opted to wear her golden tresses in a bouffant updo.