At 28, Kathryn Hahn Made A Life-Changing Decision

In 2001, a young Kathryn Hahn was faced with a momentous decision. After pursuing a theater career in New York — and a master’s in drama at Yale — she received a tempting job offer in Los Angeles. But even though the new gig would reunite her with her then-boyfriend, now-husband Ethan Sandler, the Ohio native wasn’t sure if she was ready to go the Hollywood route, having just landed the lead role in the touring production of the Tony Award-winning Proof.

“It felt like a crossroads of my life. Which way am I going to go? My boyfriend was like, ‘We've been apart for three years. How are you going to go on for another year?’ That, coupled with the student loans, made it an easier decision,” Hahn, now 51, tells Bustle. “But I was kicking and screaming, and I really felt this ache in my soul and my belly for a long time, because all I had known was theater — except for a kids’ TV show I did when I was like 11.”

The LA job was a part on the NBC crime drama Crossing Jordan — and it turned out to be her big break. Shortly after, she got the role of Kate Hudson’s best friend, Michelle, in How To Lose a Guy in 10 Days.

“We were shooting in Toronto, and I couldn't believe that at the end of it, I was going to see my name on a screen,” Hahn says. “I'd never worked with stars like [them] before. So even to be around Kate and Matthew [McConaughey] was like, Oh.”

The movie’s success helped Hahn nab memorable supporting roles in hit comedies like Step Brothers and Bad Moms, and scene-stealing parts on TV shows like Transparent and Parks and Rec. Now, she’s taking the lead as a wily but powerless witch in Disney+’s Agatha All Along — a show built around the delightfully campy character she first played in Wandavision.

If only her 28-year-old self could see her now. “Looking back, everything seems so life or death. Every one of those big decisions you just think, ‘This is going to determine the rest of my life,’” she says. “You're able to see it all fall into this perfect, weird plan that I was not even aware I was part of.”

Below, Hahn opens up about life at 28, from her friendships and the benefits of anonymity to almost getting in a boating accident with Hudson.

Looking back at your big decision to move to LA at 28, would you have done anything differently?

I wonder now if I would have made the same decision, and I guess I would have. At 28, it's a really unsettling time, because your 30s seem so daunting and so adult, and your 20s feel like you're in them forever, like you're always going to be able to smoke as many cigarettes as you want. You're always going to be able to drink until 4 a.m. and wake up and work like three hours later. And you always think that your friendships are going to last for the rest of your life.

Speaking of friendships, did you have a close group of friends at 28?

I had a dear group of friends from Northwestern. Those friends that you meet in college are the ones through whom you see the world. My boyfriend, now hubby, Ethan, was definitely a part of that as well. I met some of my closest friends at Williamstown [Theater Festival].

Also, your career was really taking off around that same time. How did that affect everything that was going on in your personal life?

It was interesting because for so long, we were all in the same boat of off, off, off, off Broadway and hustling and borrowing money from each other, and going to this theater festival. I had no money behind it, but I wrote Ethan a check for 1,000 bucks. I said, “I promise you, I'll pay you back because it was the only way I can afford going to Williamstown.” He just held on to it, never cashed it.

But then we all started getting jobs that took us away from each other. People moved to different places; new chapters and big relationships started. So when I started working — I still couldn't believe when I left the hair salon that I wouldn't have to go back — everybody had different paths and timelines, like some people worked right off the bat, and some people that took a hot second. I guess that's when life starts to feel unfair. But again, you never know how it's gonna pan out.

I feel like a lot of people, especially in their late 20s, can relate to that feeling of drifting apart.

If you partner with somebody, or if you see your friend starting to partner with somebody, all of a sudden you feel a little bit groundless. I remember being in my 20s. When I picture it, it's all in light, and I remember looking down the barrel of 30 and seeing this dark cloud start to descend. There is a feeling that all of a sudden summer's ending — the summer of your 20s — and it's a lot. You're not on your parents’ insurance. You're launched. If you're living in an apartment with seven other people, you start to think, like, What the hell? Is anything ever going to happen? Am I ever going to be able to be on my own and grow up?

I also want to talk about How to Lose a Guy in 10 Days. Tell me about your favorite memory from filming the movie.

Oh, there are so many good memories. Kate's family had a summer home near the lakes outside of Toronto. I remember being on an inner tube and being driven around the lake by her. Kate was, of course, piloting the boat. It was so freaking bumpy. I felt like my bathing suit was gonna fall off. We both looked at each other, and couldn’t believe this was happening. Are we gonna die in this lake in the middle of doing our first movie?

That sounds incredible. I do love when you play the fake therapist in the movie. I was wondering how that scene came together.

It was in the script, and we were all really excited about that scene. I was especially excited about the Sally Jessy Raphael glasses. I had very little sway, except in that department, where I was like, “I think she needs to have these frames.”

I remember the day, there was a lot of improvising. It was very hard to not break, definitely for Kate and me. Every time we looked at each other, we would start laughing, and Matthew was just so game, going along with everything that was spitting out of our mouths. When she took the napkins and put them in her armpits, I was going to lose my mind. It was also so slap happy, like we were in someone's actual apartment, and it was so hot. There were so many bodies and lights in there. Everyone was sweating profusely. I don't think Matthew was because he was just so cool as hell.

As you became more famous, did you feel any additional pressures when choosing roles?

No, because I was under the radar for so long — like so, so long. A lot of it at the beginning was just what was offered to me. Sometimes I joke in fittings, “If it fits, I'm wearing it.” But that was how it was. If you got something, there was no real luxury to say no.

So things accumulated in this weird stew of like a comedy, dramedy, drama, sitcom, movie, or TV show pilot. There was no real plan, and in public, no one recognized me. Nobody recognized me and they actually still don’t sometimes. That's why I've been able to have this weird, chaotic, gorgeous career because I've been able to do all these different parts. The benefit of no one knowing me really worked in my favor. I'd walk into some of those audition rooms, and people would think that they were seeing this person for the first time. I didn't feel pigeonholed.

This interview was edited and condensed for clarity.