A New Chapter in Leading Roles
For years, audiences knew Joel Courtney as the lovable, supportive best friend Lee Flynn in the global phenomenon The Kissing Booth. Now 30, the actor is ready to shift into the spotlight as a romantic lead. In his latest project, 40 Dates and 40 Nights, Courtney stars alongside Bailee Madison in a story centered on a high-stakes bet.
The plot follows Leah, played by Madison, who strikes a deal with her grandmother (Annie Potts) to go on 40 dates with 40 different men in exchange for a year of rent. The plan hits a snag, however, when a disastrous first encounter with Mason (Courtney) sparks an unexpected connection, threatening to upend her entire experiment.
The Evolution of a Leading Man
Reflecting on his career path, Courtney credits his time in the Netflix trilogy for preparing him for this transition. «I absolutely cherish my time on The Kissing Booth,» he shared. «I learned so much on those films about the structure of rom-coms and the moments of connection between costars. Getting to play the leading guy now, I just felt ready.»
Chemistry and Collaboration
Working with 27-year-old Bailee Madison made the leap to a leading role seamless. The two shared a pre-existing friendship, which added a layer of authenticity to their on-screen dynamic. Courtney noted that while much of the film’s dialogue feels spontaneous, director Andy Delaney insisted on thorough rehearsals to fine-tune the chemistry between the leads.
«I love rehearsing — I think it is central to my process,» Courtney explained. He highlighted a pivotal scene on a couch, where a playful night in escalates into a moment of realization, as a prime example of the benefits of detailed preparation.
A Return to Classic Romance
Courtney is deeply enthusiastic about the script penned by Sarah Howard, describing it as a «beautiful piece with beautiful characters.» For him, the movie captures the magic of early 2000s romantic comedies, emphasizing genuine humor and relatable storytelling. He believes the current surge in popularity for the romance genre is a reaction to our increasingly digital lives.
«I think that’s where these films really score, is when you see yourself in them,» says Courtney. He encourages viewers to embrace the unpredictability of romance:
«This outcome is not impossible; it’s achievable. You gotta keep trusting that love is out there, keep trusting in 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.