Chances are, you probably have a crush on Jon Hamm (or you will as soon as you Google him—I don’t make the rules!). Chances *also* are, you probably don’t know that he’s currently engaged (!!) to his girlfriend Anna Osceola, whom he reportedly proposed to back in February. Sad for you, but happy for Jon because he truly seems to be living his best life alongside the fellow actress. Learn more about Anna below, starting with the fact that…
She’s an actor as well!
Anna actually made her acting debut way back in 2007 when she appeared in the television movie Not Another High School Show, and she has since gone on to star in tons of other projects, including a three-episode arc on Greek and roles on Rizzoli & Isles, NCIS, Law & Order: Special Victims Unit, and Law & Order True Crime. That said, one role in particular is uniquely special because it’s how she met Jon! Enter: A show you may or may not have heard of called Mad Men, lol.
15 years ago today, we met the world’s greatest pitch man.
Tell us your favorite moments from the series. #MadMen pic.twitter.com/RbmNIVrZRz
— AMC+ (@AMCPlus) July 19, 2022
Yep, the duo reportedly first crossed paths while working on the set of the hit series, during which Anna played the receptionist at Esalen—aka the California retreat that Jon’s character, Don Draper, goes to during the show’s final episode. Mad Men wasn’t the last time the couple worked together either, since they also shared the screen for the third installment of the Fletch series, Confess, Fletch, after they started dating in 2020. Cute pics from the film’s premiere, incoming!
The project was a huge milestone for Jon, who dished to Insider, “It’s exciting to have gone on this journey and actually have people get a chance to see it. It’s very different. It’s a reboot, rebranding, reimagining, a reintroduction to this character to a whole new generation and that’s a fun challenge… It’s exciting as an actor to kind of put your stamp on something so specific.”
Anna and Jon dated for two years before getting engaged 💍
Anna and Jon were romantically linked in 2020 after being spotted multiple times together looking very much in love; but Extra reported the couple was actually first captured on camera back in 2017 at a coffee shop. Once it seemed the two had made their ‘ship ~official~ official, they were seen pretty much everywhere, including playing tennis, going to the beach, and even vacationing in Italy in September 2021.
The two upped the ante in March 2022 when they made their red carpet debut at the Vanity Fair Oscars afterparty.
Since then, Anna and Jon have gone on to make more red carpet appearances, the most recent of which low-key confirmed their engagement!
Just last month, Anna showcased her stunning, diamond ring at the 2023 Vanity Fair Oscars afterparty just one year after going red carpet official and I, for one, have yet to recover. Get ready to pull out a magnifying glass and witness that 💍:
She “opened up the possibility of things” for Jon 🥺
During a September 2022 SiriusXM interview with Howard Stern, Jon actually opened up about his relationship with Anna, even saying he could see himself making a more serious commitment down the line (remember, these two hadn’t been engaged at this point!). “This is all part of what I’m saying. This is another place in my life that I feel very settled and comfortable. I’m in a relationship right now and it’s comfortable,” the actor said, adding that he was working on his mental health and seeing a therapist.
The star also revealed that, over the course of the past few years, he’s finally started “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.”
“It sounds hokey and whatever, but it’s real and for one of a better word, it’s what I’m working for. What else is there other than that?,” he added before confirming that he is “very much so” in love with his now-fiancée. Obsessed!
Anna is super low-key
And, turns out, it truly is a value both she and Jon share! Jon even openly discussed his and Anna’s decision to keep certain things private and set boundaries—such as no social media in a very public-facing industry—telling InStyle in 2017, “The point of life is not to put dog ears on yourself and post it online for everyone to see.”
“It’s fun, it’s adorable, but it’s the visual equivalent of masturbating—there’s no point other than immediate gratification,” he continued.
Aaaaaand that’s pretty much all we know for now, but make sure to check back in on these lovebirds as we get more updates on ’em ❤️.