*This article is from our September 2025 issue – scroll down to flip through the issue for free or order a print copy here.*

Created by Hillary Lewis and Lauren Rebecca Davidi, Chasing Cupid is a quirky new comedy web series about a group of 20-somethings and their friendships as they navigate the disastrous world of dating and relationships. StarShine recently had a Q&A session with Hillary, who also plays Maisey in Chasing Cupid, along with the rest of the cast: Isabelle Hahn, Elina Yael, Annie Jean Buckley, and Natalia Estefania Polo, and got the details of this new series, which is available now on YouTube!

For those readers who haven’t seen Chasing Cupid yet, why don’t you tell us what the series is about?

Hillary Lewis: Chasing Cupid is a comedy/drama web series that is centered around a group of friends that are navigating life post college. It’s filled with laughter, tears, and heartbreak, but the friends support each other through it all.

What is your favorite trait about the character you play? Least favorite trait?

Hillary Lewis: Her sense of humor. Maisey is a comedian at heart and I love how she isn’t afraid to be herself.

Isabelle Hahn: I love how bold Apple Moon is.

Elina Yael: I love how supportive Piper is of her friends, even in the moments she wants to roll her eyes at them. She takes the approach of ‘I’ll be here to support you no matter what’, and we all need that friend!

Annie Jean Buckley: Cece is so optimistic! I don’t think I have a least favorite trait. I would say maybe I worry and want to protect her for being too forgiving sometimes.

Natalia Estefania Polo: My favorite trait about Sophia is her quiet resilience. She’s working hard to remember her worth during a difficult season, and I admire that. She feels things deeply but keeps going, which I strive for too. If I had to pick a least favorite trait, it would be that she can be a bit reserved, though I don’t see it as a weakness—just something she works on as the series progresses.

 

Do you have a favorite scene that you filmed?

Isabelle Hahn: The park scene in episode 2! Looking up and seeing the Hollywood sign while filming was so iconic.

Elina Yael: It was really fun shooting the tarot card reading scene in front of the Hollywood sign. It was a beautiful day and we all had lots of fun playing with the scenery and lighting.

Annie Jean Buckley: I loved the park scene with Isabelle (Apple Moon) and Elina (Piper). I just feel like it was so natural for us to film that scene, the dynamic relationship of it. You could really see our friendships shine through.

Natalia Estefania Polo: Yes! My favorite scene has to be when Sophia meets the rest of the girls at the party. I think it’s such a great introduction to their dynamic! It’s not just funny, but also a little awkward in a very real way. I love how it sets the tone for their relationships moving forward.

Hillary Lewis: Definitely the restaurant scene because I had my dog, Winnie, with me. It was kind of hard because I had to make sure Winnie was behaving LOL, but it was overall so fun.

What do you hope viewers will get from the series?

Annie Jean Buckley: I hope they’re reminded they haven’t met everyone they’re going to love yet—whether platonic or romantic. Getting out there, even in an intimidating city like L.A., can be so rewarding.

Natalia Estefania Polo: I hope they feel the same comfort and connection that shows like Sex and the City gave so many women. Chasing Cupid explores friendship and self-worth in an honest way, and I want viewers to feel validated in whatever season they’re in, especially if it’s a hard one. And to remember they’ll always have their friends.

Hillary Lewis: I hope they realize love doesn’t have to be stressful—it can be fun. And I want them to see how important friendship is, because your friends will stick with you through thick and thin.

What would you like to say to all of your fans and future fans reading this?

Isabelle Hahn: Hey baddies! Love you.

Elina Yael: Hi! I love you so much and thank you for sticking around and supporting me. You all mean the world, and I couldn’t do this without you!

Annie Jean Buckley: Independent filmmaking in any medium needs all the support it can get. Making art is so important for people to connect and it takes a lot of work and heart! So, any love and support goes a long way! Thank you!

Natalia Estefania Polo: Thank you so much for supporting me and for watching the show! I hope you really enjoy what you’ve seen so far. Love you.

Hillary Lewis: Thank you for all your support. It means the world to me. Never give up on your dreams, keep going at them! And lastly, be yourself always.

Watch the two episodes of Chasing Cupid here!

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