After years of playing the supportive, endlessly charming best friend who helped others secure their happily-ever-afters, Joel Courtney is finally stepping into the spotlight as a bona fide romantic lead. Best known for his breakout role as the lovable Lee Flynn in Netflix’s massively popular The Kissing Booth trilogy, the 30-year-old actor spent years watching his co-stars navigate the highs and lows of cinematic romance. Now, he is capturing hearts of his own opposite Bailee Madison in the delightfully chaotic new romantic comedy, 40 Dates and 40 Nights. The film follows Madison’s character, Leah, who reluctantly agrees to go on forty different dates with forty different men in exchange for a year of free rent from her grandmother, played by the legendary Annie Potts. However, the structured corporate-style dating experiment quickly goes off the rails when an incredibly disastrous first date with Courtney’s character, Mason, keeps pulling the two back together, sparking an undeniable connection that threatens to ruin her grandmother’s strict challenge.
For Courtney, transitioning from the ultimate platonic sidekick to a charming leading man felt like a natural evolution rather than a jarring leap, thanks in large part to his formative years on the set of The Kissing Booth. Reflecting fondly on his time with the franchise, he recognizes that watching the central romance unfold between his former co-stars Joey King and Jacob Elordi served as an invaluable masterclass in the genre. He explains that those years taught him the delicate architecture of on-screen relationships, the importance of comedic timing, and how to build those quiet, electric moments of genuine connection that keep audiences rooting for a couple. Armed with those years of observation and preparation, when the opportunity arose to finally play the guy who gets the girl, Courtney felt entirely grounded, confident, and ready to bring his own unique brand of warm, relatable masculinity to a leading role.
The transition to leading man was made infinitely smoother by the presence of his co-star, 27-year-old Bailee Madison, whose effortless talent and collaborative spirit set a remarkably warm tone on set. The two actors shared a natural, easygoing chemistry that jumped off the screen, a dynamic undoubtedly bolstered by the fact that they had been close friends in real life long before they were ever cast as lovers. Having run in the same industry social circles with a web of mutual friends for years, they skipped the awkward get-to-know-you phase typical of new co-stars and jumped straight into building a convincing, layered relationship. Courtney speaks of Madison with immense respect and admiration, describing her as a first-class professional who is exceptionally kind, creative, and generous as a scene partner, turning long days on set into a genuinely joyful collaborative experience.
While their natural real-life friendship provided a solid foundation, the pair worked tirelessly with director Andy Delaney to ensure that the emotional beats of Leah and Mason’s evolving relationship resonated perfectly. Courtney, who considers detailed rehearsal central to his artistic process, relished the opportunity to dissect the script’s emotional nuances, balancing highly structured, practiced moments with bursts of spontaneous improvisation. While some of the film’s lighter, more chaotic scenes—such as a frantic, comedic pharmacy run to secure Plan B after a one-night stand—relied heavily on the actors’ quick-witted ad-libs, other intimate moments required meticulous preparation. Courtney specifically recalls spending hours rehearsing a pivotal, tension-filled living room scene where Mason spends the night on Leah’s couch during a power outage, a vulnerable sequence where their playful banter subtly shifts into a deeper, slightly dangerous romantic awareness that he credits Delaney and Madison with helping him fully unlock.
At its core, the film’s emotional depth is anchored by the rich screenplay penned by Sarah Howard, whom Courtney eagerly praises for creating a story filled with believable, multi-dimensional characters and a rare level of emotional nuance. He proudly notes that the project captures the nostalgic, comforting essence of the classic early 2000s romantic comedies that audiences still endlessly rewatch, delivering honest laughs and heartfelt moments that feel organic rather than forced. In an era where the romance genre is experiencing a massive pop culture renaissance, Courtney attributes the collective craving for stories like 40 Dates and 40 Nights to a deep-seated societal desire for genuine human intimacy in an increasingly isolated, digitized world dominated by transactional dating apps and superficial social media interactions.
Ultimately, Courtney believes the true magic of a great romantic comedy lies in its ability to offer viewers a sense of hope and self-reflection, reminding them that finding a deep, meaningful connection is still entirely possible if they are willing to take a leap of faith. He hopes the film inspires audiences to step outside of their comfort zones, put down their screens, trust their instincts, and remain open to the beautiful unpredictability of real-world encounters. By portraying a love story that feels both aspirational and deeply grounded in reality, Courtney successfully completes his journey from the supportive best friend to a memorable romantic lead, leaving audiences thoroughly charmed. For those looking to dive headfirst into this heartwarming, nostalgic journey, 40 Dates and 40 Nights is currently available on demand.
