Kat Dennings Isn’t Living Life By Milestones

When it comes to Kat Dennings’ role as Jules on Dollface, life comes pretty close to imitating art — and not just because her real-life fiancé appears as the object of her affection on the show. Season 2 of the Hulu series offers many parallels to Dennings' personal life and experiences, and, to hear Dennings tell it, they only deepened her connection to her character.

The new episodes follow Jules as she makes several adjustments to her life as her 30th birthday looms. She finally decides to quit her job as Celeste’s right-hand woman and pursue her passion for graphic design (the Great Resignation has come to Woom) and learns what she needs in a romantic partner (goodbye, veterinarian who can’t cut ties with his ex). “She's taking steps into being a formed human,” the actor tells Bustle of Jules’ self-actualization.

At 35, Dennings is doing some self-actualizing, too. After entering Hollywood in 2000 with an appearance on Sex and the City and later starring in Marvel blockbusters, she finally mustered the courage to try her hand at writing material of her own. First, she’ll adapt one of her essays into an episode for the upcoming anthology series Girls Can't Shoot (& Other Lies); she has a few more writing projects that are still under wraps.

Like Jules, Dennings is also still finding the balance between prioritizing adult friendships and romantic relationships. “I have to really remind myself to be on the ball a little bit more because, yeah, I can be absent minded,” she says of her tendency to go stretches of time without speaking to her equally busy friends. Now that she’s found “the right person” — rock star fiancé Andrew W.K. — she’s no longer caught in a constant juggling act. But she did shock her followers when she announced her engagement to W.K. only a week after going Instagram official with him in May 2021. “It was a wonderful, joyful thing,” she says, politely agreeing to disagree that the post brought the internet to its knees. Even so, Dennings is beaming about the “magical” update to her longtime crush on the musician.

Below, Dennings discusses Dollface Season 2, her relationship with Andrew W.K, and her favorite celebrity baby announcement.

In this season of Dollface, Jules finally gives herself permission to dream big and actually go after what she wants. Did that resonate with you, personally?

Something I've always done and wanted to do but I never really had the courage to go for it was writing, and I have a couple of things in development now. I had to talk myself into this thing, like, "You know what? Who said you weren't good enough? And why do you think that? And why not?" I had to bite the bullet. And it's very vulnerable. But I'm so glad I did, and now it's a big new part of my life.

The women in the show are approaching their 30s in drastically different ways: Jules is nonchalant about it, while Madison is determined to have everything in order before hitting the milestone. What was your 30th like?

I remember feeling like it should feel like a huge giant deal, and it just didn't. I don't even think I did anything. I felt that pressure, I guess, to have it "together." What does that even mean anymore? Nothing. It's like we all have this pressure put on us by some ethereal force about things you have to do or have done by a certain age, and it's just made up. Especially for women, we're told stupid things that we have to do or have done by certain ages. Absolutely untrue and false.

On the show, Jules’ friend Izzy overthinks posting a photo of her new boyfriend on Instagram. Did you and Andrew W.K. have a conversation before going Instagram official and posting your engagement?

On one hand, you're really excited and you want everyone to know certain things or whatever. But on the other hand, you're like, "Well, as soon as I invite people into this, it's sort of giving permission to people to know things." It's kind of a double-edged sword, but as soon as we were engaged, it was obviously fine to post. It was a wonderful, joyful thing. But yeah, I remember as a youngster, I definitely learned that lesson of like, eh, maybe don't post everything as it happened. Maybe take a moment and really think about it, and that's just how I do it.

I love when people post, like, "Surprise, I'm married."

I love that. I love that. And not to shout anybody out, but when Alexis Bledel was like, "Hey, I’m married and have a kid!” I thought that was the coolest thing anyone has ever done. I just admire that so much. I wish her the best. I always admired that when people kept things really private and then just surprised.

And I love that you sort of manifested this relationship by tweeting at him, calling him a tall drink of milk back in 2014.

I know. I don't even remember doing that. I've always been a huge fan of him and his music — he was obviously just a talented, amazing genius. I've just always admired him. And so it is a very strange and magical update to that story.

You previously said that, like Jules, you tend to fall off the face of the Earth when you enter relationships. How would you describe your friendships now and your dynamic with Andrew W.K.?

I, as a person, get overwhelmed really easily. Any time I have something big to focus on, I kind of just drop out. It's not something I intend to do. I blink and it's a month later. That's just my personality, unfortunately. But I've actually been a lot better, I think. And it's probably due to finding the right person and not feeling panicked and stressed out all the time, that's it. Finding the right person, being really comfortable, and feeling at ease. It's a tall order, but it can be done.

This interview has been edited and condensed for clarity.