Joel Courtney on Being a Leading Man in 40 Dates and 40 Nights

Joel Courtney spent years making audiences root for someone else’s love story. Now, he’s finally taking center stage.

After winning over fans as endlessly lovable best friend Lee Flynn in Netflix’s The Kissing Booth franchise, Courtney, 30, steps up as a full-fledged heartthrob opposite Bailee Madison in 40 Dates and 40 Nights. The rom-com follows Leah (Madison) as she agrees to go on 40 dates with 40 different men after her grandmother (Annie Potts) offers her a year of free rent if she completes the challenge. But when one disastrous first date with Mason (Courtney) keeps bringing the pair back into each other’s orbit, their unexpected sparks threaten to derail the entire experiment.

In the latest issue of Us Weekly, on newsstands now, Courtney shares how his years playing the lovable best friend helped him prepare to finally be a leading man.

“I absolutely cherish my time on The Kissing Booth,” he tells Us, noting that he “learned so much on [those films] about the structure of rom-coms and the moments of connection” between his costars Joey King and Jacob Elordi, who play the trilogy’s main love interests. “Getting to play the leading guy now, I just felt ready.”

Having Madison, 27, opposite him on screen only made that transition easier.

“Bailee is an incredible actress, and so collaborative, and very kind and just a first-class person to work with,” Courtney explains. “We just had an awesome time on film… We go ttogoo to work and have a really great time making this beautiful story that I think people are going to absolutely love and connect with.”

It didn’t hurt that the pair were friends long before they were cast in the film together, making their chemistry feel even more natural once the cameras rolled. “We ran in similar circles with a lot of mutual friends,” Courtney shares.

He adds that, despite much of 40 Dates’ dialogue feeling natural and conversational, rehearsals with director Andy Delaney played a key part in ensuring the Leah and Mason dynamic landed right. “I love rehearsing — I think it is central to my process,” Courtney notes.

He adds that while some scenes played better off the cuff — one particular moment in a pharmacy where Leah finds herself desperate to get access to Plan B after a one-night stand relied heavily on improv moments, Courtney points out — others benefited from getting every beat laid out ahead of calling “action.”

“There’s a scene on the couch where [Mason spends] the night at Leah’s place because his power goes out and their friendship, their playful friendship, kind of takes a dangerous step toward, ‘Yeah, there’s something here between us,’” Courtney says. “We rehearsed that scene a ton. We had an absolute blast rehearsing that, and I got a lot out of it. I learned a ton from Andy, and I learned a ton from Bailee.”

The heart of the film, after all, stems from the world Sarah Howard created on the page. Courtney jumps to praise the writer for her script, calling it a “beautiful piece with beautiful characters and the ability to apply so much nuance.”

It’s the type of script, Courtney says, that feels reminiscent of the charming classic romantic comedies of past decades.

“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 like the laughs are honest,” Courtney explains. “I‘m just so proud of it.

The romance genre has seen a major recent comeback — People We Meet on Vacation was just nominated for an Emmy, while Voicemails for Isabelle has taken the world by storm. Courtney, for his part, thinks the resurgence comes down to something surprisingly simple: people are craving real human connection in an increasingly digital world.

“I think technology is a separator as well as a connector,” he says, pointing to dating apps and social media as changing the way people meet. “I think this pursuit of a relationship, this pursuit of love, is becoming a real thing in the rom-com space.”

For Courtney, the best romantic comedies remind viewers that love is still worth taking a chance on — even if you have to date 40 people to find it.

“I think that’s where these films really score, is when you see yourself in the. Like, I get what Leah’s going through. I wish I could find a mason,” he shares. “This outcome is not impossible; it’s achievable. You gotta keep trusting that love is out there, 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 on demand now.