Chasing Cupid

Actor
About
Raised in Los Angeles, she honed her craft through local acting classes and further developed her skills in New York, where she attended two summer programs at the prestigious New York Film Academy. Her early involvement in the Groundlings teen program provided a strong foundation in comedy and improvisation, contributing to her versatile performance style.
Beyond her work in front of and behind the camera, Lewis is also a dedicated psychology student pursuing her goal of becoming a licensed therapist (LMFT). She is passionate about combining mental health advocacy with creative storytelling to spark meaningful conversations and positive social change.
Driven by emotional depth, artistic curiosity, and a deep desire to connect, Hillary Lewis represents a new generation of multifaceted creatives seamlessly blending performance, filmmaking, and psychology to explore the human experience through art.
"Stories that heal, hearts that feel"

Interview
What was your first reaction when you read the script for Chasing Cupid? Did you immediately see yourself in your character?
As one of the creators of Chasing Cupid, the second Lauren (co-creator and director) and I wrote out the character descriptions, I knew I was meant to play Maisey. Honestly, we wrote her to be a lot like me — her personality, her chaos, her humor. Maisey has so many traits, and while she might come off as unhinged and a hot mess, there’s something very real and relatable about her. I definitely connect with her on a personal level. I don’t want to give too much away, but if you want to understand her more, stay tuned to the series
Dating in the digital age is full of chaos. What’s the most “Chasing Cupid”-like moment you’ve experienced in real life?
It’s definitely a crazy dating world, especially with all the apps and technology — it makes everything feel even more intense and unpredictable. I’ve had my fair share of “Chasing Cupid” moments, but the one that sticks out most recently is when a guy approached me at a coffee shop and asked for my number. It felt like a real-life Maisey moment because I was literally in pajamas, hair in a messy bun — totally not put together. We ended up going on several dates, and the last one was at a spa, which you’d think would be cute… but it was a total disaster.
Your character goes through some hilarious and unpredictable situations. How much of that comedy is scripted vs. improvised on set?
That’s a great question. Initially, we really wanted a hybrid structure — half scripted, half improvised — because I love improv and thought it would give the show a natural, off-the-cuff energy. Since I have a background in improv, I was really excited about that idea. But once filming started, we realized it was a bit too chaotic to manage. So we made the decision to script the entire rest of the series.
That said, we were always open to hearing ideas from our cast. We encouraged everyone to speak up if they had suggestions, and a lot of great little moments came out of that collaboration.
The series feels very real and relatable. How did you personally connect with the themes of love, friendship, and digital dating?
Lauren and I based Chasing Cupid heavily on our own lives and the world around us. Growing up in LA, we’ve been exposed to all kinds of people, relationships, and situations. Our friend group is strong — we’ve gone through so much together, including the ups and downs of dating. And yes, we’ve tried pretty much every dating app out there! The themes in the series — love, friendship, and the chaos of digital dating — are all things we’ve experienced firsthand.
Which scene or episode challenged you the most as an actor and why?
The most challenging scene for me was in Episode 2, where Maisey goes on a date with her dog. It sounds simple, but it was actually super difficult to shoot because my dog isn’t trained. I had to stay focused and in character as Maisey while also trying to get my dog to cooperate — not the easiest combo!
There’s a lot of humor in the show, but also subtle messages about self-worth and growth. What’s one lesson your character learns that you think every young person should hear?
Throughout the series, Maisey learns how important it is to love herself, even when she’s struggling on the inside or watching her friends find success in dating while she’s still figuring it out. I think that’s something everyone — especially young people — should hear: that self-love matters just as much as romantic love, and that your person will come when the time is right.
Social media plays a big role in the show’s world. How do you personally balance being authentic online while navigating your career and dating life?
This is something I personally struggle with. I really do try to be authentic online, even though there’s always pressure to be liked and to present a certain version of yourself. But at the end of the day, what matters most is how you feel about yourself. I used to focus so much on being perfect — on looking a certain way and trying to fit in — but I’ve learned to be more accepting of myself. I’m not perfect, but I love who I am, and I try to show that. That’s what’s most important.
If you could give one piece of dating advice to your character, what would it be?
I’d tell Maisey to keep being herself. At some point, she starts to try to fit into the mold of what she thinks a “typical” girl should be — but that’s not who she is. And honestly, that’s something I need to remind myself of too. The right people will like you for exactly who you are.
Imagine there’s a Chasing Cupid Season 2: what crazy dating scenario would you love to explore next?
This is such a fun question! There are honestly so many ideas that come to mind, and I can totally see Lauren and I writing some really fun stuff for Season 2. One scenario I’d love to explore is a character going on a date and running into their ex — maybe at a movie theater, where the ex is working the concession stand. Another idea could be a catfish situation, which I think most people have experienced in some form. So much potential for drama and comedy!
Lastly, how has being part of this cast and project changed the way you see modern love, if at all?
Being a part of Chasing Cupid has definitely changed the way I look at love and dating. I used to take it all so seriously. But working on this series reminded me that dating can also be fun, light, and even a little ridiculous — and that’s okay. You’re supposed to enjoy the process, not stress over it!

Projects
Do you want to know more? You can find some projects below.
Spotify Playlist