Jon Hamm and Anna Osceola are engaged after two years of dating, per People. The couple first met on the set of Mad Men in 2015.
ET has reached out to Hamm and Osceola's reps for comment
Osceola, currently 34, appeared in Mad Men's final episode in May 2015. She played a receptionist at the retreat center that Hamm's character, Don Draper, attended. Several months later, Hamm, now 51, separated from his girlfriend of 18 years, Jennifer Westfeldt. He and Osceola were not romantically linked until five years later, in 2020.
In September 2022, the couple appeared together onscreen again in the comedy crime film Confess, Fletch. Several months prior, they walked their first-ever red carpet together at an Oscars after-party in March. They later appeared at the world premiere for Top Gun: Maverick and on the red carpet for Sarah Silverman's musical, Bedwetter, both in May. They also attended at the ESPY Awards together in July.
Though Hamm keeps quiet about his relationship, he confirmed his dedication to Osceola in an appearance on Howard Stern's SiriusXM radio show in September 2022. When asked if he was in love, Hamm admitted, "I very much so am."
With the news of their engagement, ET takes a closer look at Osceola's life and career.
She's originally from Massachusetts
Per People, Osceola was born and raised in Massachusetts before moving to California to pursue acting.
She has mainly acted on television
Osceola first appeared onscreen in the television movie Not Another High School Show in 2007. Per IMDb, the film is a parody of popular teen TV dramas at the time, including Beverly Hills, 90210, Dawson's Creek and Laguna Beach.
Before meeting Hamm on the set of Mad Men, Osceola appeared as a guest on several popular TV shows, including Saving Grace, Greek, Rizzoli & Isles, and NCIS.
After the Mad Men episode, she has also acted in episodes of Law & Order: Special Victims Unit and Law & Order True Crime.
She keeps her relationship private
Like Hamm, Osceola stays off social media. The couple also waited a long time to appear in public together. Though they were photographed leaving a coffee shop in 2017, the two weren't seen together again until 2020 when they were spotted in Los Angeles picking up food and supplies during the early days of COVID-19.
Hamm and Osceola took a a vacation to Italy in 2021, where they were seen relaxing on the beach together, but did not step out on a red carpet with each other until the following spring.
She appeared in Hamm's recent movie, Confess, Fletch
Hamm starred as Irwin M. "Fletch" Fletcher in the 2022 installment of the Fletch series originally starring Chevy Chase. Osceola had a minor role in the film, and accompanied Hamm to a screening in September 2022.
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