A New Romantic Chapter

After building a dedicated fanbase playing the supportive best friend, Lee Flynn, in Netflix’s hit series The Kissing Booth, 30-year-old Joel Courtney is ready for the spotlight. The actor now steps into the role of a leading man in the fresh rom-com 40 Dates and 40 Nights, where he stars alongside Bailee Madison.

The film follows Leah (Madison), who accepts a daunting challenge from her grandmother: go on 40 dates with 40 different men to secure a year of rent-free living. However, an encounter with Courtney’s character, Mason, complicates the experiment as their undeniable chemistry begins to disrupt her carefully planned mission.


The Evolution of a Leading Man

Reflecting on his career path, Courtney credits his time in The Kissing Booth for providing the essential foundation for his transition into a starring role. “I absolutely cherish my time on The Kissing Booth,” he shared. “I learned so much about the structure of rom-coms and the moments of connection” between his former co-stars.

His natural rapport with co-star Bailee Madison, 27, proved to be a significant asset. Having been friends long before the cameras started rolling, their pre-existing connection made the transition into an on-screen romance seamless.


Crafting the Perfect Chemistry

Courtney emphasizes that while the dialogue in the film often feels effortless and conversational, the success of the Leah-Mason dynamic was built through rigorous preparation. Under the guidance of director Andy Delaney, the actors focused on rehearsals to fine-tune their performances.

"I love rehearsing — I think it is central to my process," Courtney noted. While some scenes allowed for improvisation—such as a frantic pharmacy moment—other key sequences, like an intimate scene on a couch, required detailed preparation to hit the right emotional beats. He credits the experience of working with both the director and Madison as a major highlight of the production.


A Return to Classic Rom-Coms

The actor is highly enthusiastic about the script penned by Sarah Howard, describing it as a "beautiful piece with beautiful characters." For Courtney, the film captures the nostalgic charm of early 2000s romantic comedies.

“I’m so excited that people finally get to see this, because it feels like those early 2000s rom-coms. It feels so familiar, and the laughs are honest,” he explains.

Why Rom-Coms Are Resurging

As the romance genre enjoys a renewed popularity, Courtney suggests that audiences are seeking authentic human connection in an increasingly digitized world. He believes the power of these films lies in their ability to resonate with the viewer's own experiences.

“I think that’s where these films really score, is when you see yourself in them,” he says. “This outcome is not impossible; it’s achievable. You have to keep trusting that love is out there, keep trusting your gut. Go out and be willing to be affected. Put your phone down. See if someone talks to you.”

40 Dates and 40 Nights is currently available on demand.