Anna Osceola

Jon Hamm and Anna Osceola are reportedly engaged after three years of dating. The "Confess, Fletch" co-stars first met while filming the series finale of ...

[People confirmed](https://people.com/movies/jon-hamm-and-anna-osceola-are-engaged/) the news Monday, though the actor’s rep did not immediately respond to Page Six’s request for comment. What else is there other than that?” [“very much” in love with Osceola](https://pagesix.com/2022/09/20/jon-hamm-says-he-may-marry-girlfriend-anna-osceola/) and “could for sure” see himself spending the rest of his life with her.

There's no denying that Jon Hamm has his starring role as Don Draper in Mad Men, a period drama about the advertising industry in the 1960s, ...

I’m in a relationship right now, and it’s comfortable.” He also explained that dating Osceola has opened up the possibility of marriage, children, and feeling a new level of happiness. [Howard Stern](https://www.youtube.com/watch?v=EvnAzqEgtkA) on his SiriuisXM show in September of 2022 that he can see himself getting married to Osceola and that he’s “very much so” in love. The two were also co-stars in the comedy and crime movie Confess, Fletch, so to promote their 2022 film, they showed up to the screening together in September of 2022. [former co-stars](https://www.brides.com/celebrity-couples-that-work-together-5119500) are ready to take their relationship to the next level. [People](https://people.com/movies/jon-hamm-and-anna-osceola-are-engaged/) their relationship was strictly friendly. Hamm met Anna Osceola, with girlfriend of nearly two years, on set in 2015, and now the

Osceola portrayed Clementine, the receptionist at the spiritual retreat that Hamm's lead ad executive character Don Draper attended, in the series finale, ...

It sounds hokey and whatever, but it's real and it's what I'm working for." "It's also been a process of working on myself, my mental health, all the stuff with my therapist," Hamm said. "It's a feeling of taking care of someone else and being taken care of."

The 'Baby Driver' actor, 51, is said to have proposed to the 34-year-old 'Bull' actress after they first got to know each other while working on 'Mad Men' ...

'Mad Men' and 'Confess, Fletch' co-stars Jon Hamm and Anna Osceola, who have been dating since 2020, are reportedly engaged.

[said](https://people.com/movies/jon-hamm-says-hes-very-much-in-love-with-anna-osceola-as-he-talks-marriage-possibilities/) during a September episode of “The Howard Stern Show.” “I’m in a relationship right now and it’s comfortable. Representatives for Hamm and Osceola did not immediately respond Monday to The Times’ requests for confirmation. [the end of their 18-year relationship](https://www.latimes.com/entertainment/gossip/la-et-mg-jon-hamm-jennifer-westfeldt-split-breakup-20150908-story.html). [last fall’s mystery comedy](https://www.latimes.com/entertainment-arts/movies/story/2022-09-23/confess-fletch-review-jon-hamm) in which Hamm played the titular detective and she played a character billed as “Larry.” (The comedy, the third installment in the film series originally starring Chevy Chase, also starred “Mad Men” alum John Slattery.) [series finale](https://www.latimes.com/entertainment/tv/showtracker/la-et-st-mad-men-finale-recap-person-to-person-20150517-story.html). [People](https://people.com/movies/jon-hamm-and-anna-osceola-are-engaged/) reported Monday that the actors got engaged after two years of dating.

Jon Hamm and Anna Osceola are engaged, the latest NHL trade deadline rumors, the Commanders cut Carson Wentz and more in the Roundup.

Latest NHL [ trade deadline rumors](https://www.cbssports.com/nhl/news/nhl-trade-deadline-rumors-tracker-the-latest-on-potential-patrick-kane-deal-plus-devils-land-timo-meier/) ... [MLB](https://www.thebiglead.com/mlb) starting rotation power rankings [ [CBS Sports](https://www.cbssports.com/mlb/news/mlb-power-rankings-revamped-mets-rotation-hits-no-1-with-co-aces-max-scherzer-and-justin-verlander/)] Jimmy Haslam buys [piece of the Milwaukee Bucks](https://theathletic.com/4256074/2023/02/27/marc-lasry-sell-stake-jimmy-haslam-bucks/) ... Daniel Snyder's [demands anger fellow NFL owners](https://www.washingtonpost.com/sports/2023/02/27/dan-snyder-nfl-owners-dispute/) ... Commanders [release Carson Wentz](https://sports.yahoo.com/commanders-release-qb-carson-wentz-203258067.html) ... Should Marvel be [worried about latest releases?](https://variety.com/2023/film/box-office/ant-man-quantumania-box-office-drop-concern-marvel-1235536265/) ... Stock futures [up heading into Tuesday](https://www.cnbc.com/2023/02/27/stock-futures-live-update-open-to-close.html) ... Snow and [sleet to hit Northeast](https://www.nytimes.com/2023/02/26/us/snow-storm-weather-ny-northeast.html) ... Messi tops Mbappe [for Best FIFA Men's award](https://www.espn.com/soccer/paris-saint-germain--frapsg/story/4883571/lionel-messi-beats-kylian-mbappekarim-benzema-to-best-fifa-mens-player-award) ... Jon Hamm and [Anna Osceola are engaged](https://people.com/movies/jon-hamm-and-anna-osceola-are-engaged/) ... citizen killed in [West Bank admit violence](https://www.cbsnews.com/news/israel-news-jericho-hawara-west-bank-palestinians-violence-settlers-terror-attack/) ... [as massive storm moves east](https://abcnews.go.com/US/tornadoes-touch-kansas-oklahoma-massive-winter-storm-moves/story?id=97484567) ...

The two actors technically met for the first time back in 2015 on the set of Mad Men in which Hamm played the lead role of Don Draper and Osceola appeared in ...

He went on to explain that the success of their relationship is the result of “a process of working on myself, my mental health, all the stuff with my therapist and unpacking all of that trauma and realizing that when you lose someone that's so important to you, like a mother, so early, that that creates a wound that blocks a lot of that emotional accessibility. [The American West](https://www.vanityfair.com/news/2023/02/new-right-civil-war?itm_content=footer-recirc&itm_campaign=more-great-stories-022723) That blocks a lot of that availability and vulnerability.” Hamm lost his mother when he was 10 years old to colon cancer, and his father died ten years after that. “This is all part of what I'm saying. The two actors technically met for the first time back in 2015 on the set of Mad Men in which Hamm played the lead role of Don Draper and Osceola appeared in the final episode of the series as Clementine, a receptionist at a spiritual retreat Draper checks into. He and Westfeldt broke up just a few months after the end of the show after 18 years together.

“The engagement happened a while back, but they are still on cloud nine,” a source tells Us. “They have so much fun together and already feel married.” The Top ...

[Top Gun: Maverick](https://www.usmagazine.com/entertainment/news/snl-miles-teller-jokes-about-top-gun-jon-hamm-makes-cameo/) star, 51, was initially linked to Osceola, 34, in spring 2020 after being spotted together on multiple occasions. “We will continue to be supportive of each other in every way possible moving forward.” “And opened up the possibility of things like being married, having kids — you know, defining a new version of happiness, life, wellness.” Hamm confessed that “unpacking” the trauma of his childhood has helped strengthen his relationship with Osceola. While promoting the movie, Hamm gave fans a rare glimpse at the couple’s relationship. “They have so much fun together and already feel married.”

It's a feeling of taking care of someone else and being taken care of," Hamm said of the relationship now headed for marriage.

But romance between the two did not appear to bloom until 2020, [Entertainment Weekly](https://ew.com/tv/jon-hamm-anna-osceola-engaged/) noted. [ended in 2015](https://www.latimes.com/entertainment/gossip/la-et-mg-jon-hamm-jennifer-westfeldt-split-breakup-20150908-story.html). [told Howard Stern in 2022](https://www.youtube.com/watch?v=EvnAzqEgtkA). [who flirted with Hamm’s Don Draper](https://www.latimes.com/entertainment-arts/tv/story/2023-02-27/jon-hamm-engaged-anna-osceola-mad-men-confess-fletch) in the series finale. [confirmed the news](https://people.com/movies/jon-hamm-and-anna-osceola-are-engaged/) on Monday. [Mad Men](https://www.huffpost.com/entertainment/topic/mad-men)” co-stars [Jon Hamm](https://www.huffpost.com/entertainment/topic/jon-hamm) and Anna Osceola have made a longer-term commitment: They’re reportedly engaged!