Bailee Madison Talks Pretty Little Liars: Summer School & Making Music With Boyfriend Blake Richardson

PHOTOGRAPHY BY IZACK MORALES

It’s 2010, and a 10-year-old Bailee Madison is curled up in a white leather armchair, ready to tell the story of how her faith in God has shaped her fledgling career for a nonprofit video series called I Am Second. She’s reflecting on Bridge to Terabithia — the movie that launched her career — and on the person she’s becoming, already keenly aware of her emotions and how to deal with them. “I don’t get nervous,” she giggles. At the beginning of the clip, her mom kisses her and tells her she loves her. “Mom always told me when I was done with [Terabithia], you have to stay humble Bailee,” Madison says. “She continues to say that every day. Bailee, humble. Bailee, humble.”

There’s a lot of that Bailee Madison in this one — the one sitting across from me on the Pretty Little Liars: Original Sin set in late 2021, who has grown up as a working child actor and is now several years into a career that’s shaping up to be even more exciting. I’ve spoken to her three or four times over the past couple years since she began filming the Pretty Little Liars spinoff. She’s surprised to be asked about that video; she remembers what filming it was like.

“Everyone was really worried because they were like, ‘You're really young. People love to talk. It's hard growing up in general let alone under a microscope, and now you're adding how you personally live your life and your beliefs and what makes you you,’” Madison tells Teen Vogue. “My mom was having a heart attack, poor thing. And I was like, ‘But this is me.’”

Madison was born in Fort Lauderdale, Florida, the youngest of “a bunch of siblings,” she says. A “surprise” baby, but “born into so much love.” Her six siblings are much older, but she’s close with them; her sister Kaitlin Vilasuso also did some acting, and in 2018 she and Madison launched a podcast together called Just Between Us. Vilasuso inadvertently kickstarted her career: while waiting for her to finish an audition, Madison did one of her own and landed the 2006 Salma Hayek/John Travolta movie Lonely Hearts. As she told Teen Vogue in 2021, the plan was not to keep acting, but the parts kept coming — Don't Be Afraid of the Dark, Just Go With It, Wizards of Waverly Place, Good Witch, and countless others. She was a kid you saw everywhere on screen.

If you weren’t so familiar with Madison’s work before she began playing Imogen in Pretty Little Liars, you’d at least have seen the memes. The two most popular are from Bridge to Terabithia (a six-year-old Madison grinning to herself on a school bus) and a series called The Haunting Hour (an 11-year-old Madison looking concerned at her doll doppelgänger).

“They follow me,” she laughs over Zoom a few days before PLL: Summer School, the show’s season 2, premieres on Max. “They follow me like a dating history that doesn't exist for myself. They're like the exes that don't go away.” She’s decided to lean in, using the memes to promote PLL. It’s not that serious, after all. “I feel like if my six-year-old self knew that a picture of her was going to be used on a sentence that says ‘Me peeing when I'm drunk,’ she'd get a kick out of it and be really flattered, too. So I enjoy it. It keeps my family group chat moving.”

Her actual dating history is not as extensive: she recently celebrated her fifth anniversary with British musician Blake Richardson of the band New Hope Club. She remembers seeing a video of him on Instagram years before and becoming a fan; they met in passing a bit later. “I felt like I knew him honestly, even though I didn't,” she says. “It just felt right. I was like, ‘Oh, he is a wonderful person. I think he'll play some sort of a role in my life.’”

They didn’t really start talking until some time after that, when they were both 19. Their relationship began long distance, mainly over FaceTime.

“I’m proud of our 19-year-old selves for surviving distance and also trying to navigate and grow in your twenties,” she reflects now. “I feel like in your twenties, you're constantly kind of becoming a new version of yourself, so it's a new version to love and understand and nurture and listen to. I've always had the most respect for his work ethic and the way that his mind thinks and works and operates and hears music.”

The couple has just moved into a home together with a music studio in the back, which is now useful for both of them. Earlier this year, Madison released her first song, “Kinda Fun,” which she created with Richardson. He knew that Madison wanted to make music alongside her acting career, and so he kept an ear out, sending her ideas when she was away filming.

They wrote the song last year, after a long week of family commitments, and after the SAG strikes began. She’d been mulling over what it might look like to write and make music properly, how she might push past any nerves or insecurities and just do it for herself. One night, Richardson proposed they go and just “try to have a laugh." Who cared if no one heard it? The result is the poppy “Kinda Fun,” a lighthearted bop about just enjoying life and feeling good about yourself.

“Now it's so fun because we're writing together,” she says. “We get to just wake up and have coffee and sit outside and then go into the studio and write songs, and it's really special … a bonding experience.” She’d like to make more singles, maybe an EP, but says she doesn’t feel the need to rush.

A couple years ago, before Pretty Little Liars premiered, Madison and I talked about moving through your twenties and realizing the people you’re close to might not be the people you’re supposed to be around long-term. How part of getting older is learning how to advocate for yourself in friendships and in work settings. Madison wasn’t so worried about Hollywood changing who she was as a person, or dealing with heightened scrutiny — she knows who she is, but how do you convey that to others?

Now, in 2024, Madison finds herself in a different place on those fronts. Her time on PLL has strengthened her sense of her own abilities — “It feels good to feel like I'm finally honoring my voice a bit more and my opinion.” Meanwhile, her life experiences have led her to old and new friendships that just feel right.

“What's really special is there's an awareness between myself and anyone that's in my life about the stage of life that we're all in,” she says. “There's not just a need, but also a want to have those conversations and to help each other through the questions that might come up when you're navigating your twenties and you're trying to figure out your place in this world and in yourself and in your relationships.”

It’s something her PLL character is figuring out, too, though with admittedly more intense trauma; in Summer School, Imogen is continuing to grieve the loss of her mother, figuring out her relationship with her baby’s adopted parents, and also experiencing the highs and lows of high school while being stalked by a new “A.”

“Bailee's had inspiring scenes as an actor to watch her play,” her costar Maia Reficco tells Teen Vogue on the set of Summer School. “She's the best, I love Bailee. I look up to her a lot.”

The real-life friendship among Madison, Reficco, Chandler Kinney, Malia Pyles, Zaria, and Mallory Bechtel feels palpable. It’s something Madison doesn’t take for granted. “The sisterhood and the womanhood that I've been able to actually feel for once in my life fully… is a big part of why I would [like to be on] the show for just a lot of years to come,” Madison says.

Madison calls herself a work in progress, though talking to her, you feel like you’re talking to someone who really knows themselves, who has known herself since she was the little girl grinning with her baby teeth talking about her dreams. Maybe it’s part illusion, part wishful thinking, part truth. She’s an actress, after all.

“I've been doing this job since I was six years old, and I've had to constantly reinvent myself for people to stay interested while at the same time learning about myself because I started so young,” she says. “So you do both of those things for 20 years, and obviously habits are going to be formed and then you're going to be so insanely aware that everyone has an opinion. So it's just blocking out the noise that I know won't serve my soul because I feel like the only way that you can actually [achieve] the dream that you want is if you are just listening to your moral compass or your heart compass or your mind and betting on that.”

“I was very good at betting on myself when I was younger,” she adds, young Bailee Madison never far away. She’s turning 25 this year, and she has had those years where she’s confused, or insecure, or not sure what anything is for in the end. She’s gotten through them with curiosity about herself and the world around her. “I feel like I'm now really living in my twenties and a lot of growth has come from that. There's a fire that's [been] relit."

Originally Appeared on Teen Vogue

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