Jon Hamm and Jennifer Westfeldt Almost Beat the Hollywood Curse

What's the saying? Mad men finish last?

Jon Hamm smiling wearing a tux with Jennifer Westfeldt in an evening gown
Photo: Getty Images

When Mad Men first premiered in July 2007, the world was quickly entranced by its star, Jon Hamm. Where had this handsome, 30-something actor been all these years?

But I, for one, knew exactly where Jon Hamm had been. He'd had a part in the indie film Kissing Jessica Stein, and another one in Ira and Abby — both written by and starring his long-time partner Jennifer Westfeldt. Kissing Jessica Stein played on repeat in my household growing up, and I recall being acutely aware that the star of the film was also its co-writer. As the writer and star of honest, funny indie films that spoke directly to her experiences, Westfeldt had the kind of career that I, a young Jewish girl, aspired to have.

So even when Jon Hamm became an overnight success — touted as Hollywood's latest heartthrob — and was the subject of the inevitable onslaught of "he's married to who?" articles, I still never saw Jennifer as Jon Hamm's girlfriend. For me, it was always the other way around. She was the real star.

How They Met

Jon Hamm wearing a suit sitting at an awards dinner with Jennifer Westfeldt, who is wearing a brown evening gown
Jason Merritt/Getty Images

As I got older and began to pursue the sort of career Westfeldt has, joining a creative community and consequently dating within it, Jon and Jennifer's relationship became a sort of gold standard. After all, they'd first met at a mutual friend's birthday party — then just two struggling actors — and later reconnected to run lines together, a story almost remarkable in its mundanity.

In the years that followed, it was clear the two supported each other in their artistic endeavors, at times working together, and other times not. And what's more, Westfeldt and Hamm are about the same age — a rarity in Hollywood. One would expect that the moment Hamm got mega-famous, he'd ditch his age-appropriate girlfriend for a shinier, less ambitious model. It's what the tabloids constantly speculated, and it's what pop culture history has proved inevitable time and time again (the old Hollywood curse).

Their 18-Year Union

As a woman, there's that age-old idea that you must sand yourself down — be easy, less complicated — in order to get the guy. I got the sense from her deeply personal films that Westfeldt was not doing that in her relationship with Hamm. Their relationship was a win on behalf of all brainy, neurotic Jewish girls everywhere.

As time went on and Hamm and Westfeldt's relationship proved steady; they even united all of their funniest friends for 2011's Friends with Kids (with Westfeldt writing, directing, and starring, and Hamm co-starring and producing). Believe it or not, it can be difficult to meet a guy who is cool with a woman's ambition. I still held steadfast that somewhere out there was a guy who would be cool with whatever success I had or might come into, and that our artistic pursuits would fit together seamlessly, each of us guiding the other toward our best selves. That, like Hamm and Westfeldt, we could weather the storm that is Hollywood, and that despite the inevitable ebb and flow of success, together we would find a way to keep our metaphorical boat steady.

The Breakup

But the inevitable shoe dropped, and my hope was extinguished. In 2015, Hamm and Westfeldt announced they were splitting after 18 years together. There were the requisite declarations that they remained committed to supporting each other moving forward, and when Hamm finally took home the Emmy for Outstanding Actor in Drama Series a few weeks later, he thanked Westfeldt in his speech. Following their split, there was speculation that Hamm's substance abuse issues had driven the couple apart. But perhaps their romantic partnership just ran its course. If they couldn't make it work, who can? I thought.

Where Are They Now?

Now, flash forward to today, and after years of rumored flings, Hamm has finally found love and happiness again: With his 17-years-younger former Mad Men co-star, Anna Osceola. They were first spotted together in 2020 and appear to still be going strong. Meanwhile, if Westfeldt has any type of new paramour, it hasn't been covered by the press. It would be sad, if it wasn't so predictable. As for me, I'm done looking for the Jon Hamm to my Jennifer Westfeldt; being the Jennifer Westfeldt to my Jennifer Westfeldt is enough for now.

Breakups That Broke Us is a weekly column about the failed celebrity relationships that convinced us love is dead.

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