You can ask me just about anything and I’ll probably have an answer. Put me in front of actors I genuinely admire, though, and my brain decides it’s time to clock out.
That’s exactly what happened when I sat down with Joel Courtney and Andy Delaney.
I’ve interviewed celebrities hundreds of times, but the interviews that make me the most nervous are always the ones tied to projects I genuinely love. Suddenly I forget people’s names. My carefully planned questions disappear, and I’m just trying to remember how to form complete sentences.
Thankfully, 40 Dates and 40 Nights was worth the temporary panic.
The film follows Leah, a woman who’s completely burned out on dating and ready to give up, until her grandmother offers her an irresistible challenge: go on 40 dates in 40 nights in exchange for a year’s worth of rent.
Honestly?
In this economy, most of us would at least consider it.
Directed by Andy Delaney and starring Joel Courtney alongside Bailee Madison, 40 Dates and 40 Nights is a romantic comedy. The movie has sharp dialogue, great pacing, and a refreshingly honest look at modern dating. It pays homage to the rom-coms we all grew up watching while still feeling current, exploring everything from dating fatigue to the walls we build to protect ourselves.
One of the things I appreciated most is that the movie understands the biggest challenge isn’t finding someone to date—it’s being willing to let someone in.
So naturally, the first thing I wanted to know was which romantic comedies, past and present, inspired Delaney’s approach to directing the film and helped Courtney shape his character of Mason.
THE PRETTY WOMAN OF IT ALL
Delaney was the first to chime in, “Weirdly, I looked at a load of them and one thing that I directly took was from Pretty Woman. And it was for the role of that Jai Rodriguez plays — the maitre d’— we kind of based the tone of his delivery, his performance, on the hotel manager in Pretty Woman. So because there was a kind of father figure aspect to him — he’s got a paternal and caring kind of attitude towards Bailey’s character that I felt was important because it was— she’s very exposed, she’s going on 40 dates, that’s not necessarily the safest or most secure thing to do, and his presence there really helped to reassure her, so that was a lift from Pretty Woman.”
Jai is hilarious, delivering some of the film’s best laughs, but his character serves a much bigger purpose than comic relief. He’s Leah’s safety net—the friend making sure she never has to navigate the chaos of modern dating alone.
Whether he’s keeping an eye on her dates, offering unsolicited commentary, or silently judging right alongside her, he’s always in her corner.
Every romantic comedy needs that one friend who’s willing to say what everyone else is thinking.
Jai’s character is that person, and the movie is better because of it.
Joel added, “That’s awesome, I didn’t know that, I’ve never heard you say that before.”
PROUT OF THE FILM
He then added, “For me, I feel we all had a clear goal of, you know, reaching back into the classics, like early 2000s rom-coms. Maybe that’s not the best way of saying it. Not reaching because this is its own film. It has its modern feel. But we were looking for something classic and just playful and fun, something that’s relatable. Across a bunch of different age groups, age ranges. And I’m so proud of this film. I think that we will achieve it. It’s so fun. It’s a fun feel-good movie that also gets you thinking and kind of gets you a little introspective, I think, which is exciting.”
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One of my favorite moments from the interview was laughing about just how exhausting it would be to go on 40 dates.
Honestly, I’d tap out long before date number 40.
What I loved about Courtney’s character of Mason, though, is that he never gave up. His first date with Leah is an absolute disaster, and most people would’ve walked away thinking, “Well… that’s never happening again.” Blocked. Deleted. On to the next.
Not Mason.
He keeps showing up.
That’s what makes his relationship with Leah so enjoyable to watch. The movie doesn’t rush their romance or rely on one grand gesture. Instead, you get to see every little moment that slowly brings them closer together. By the time they fall in love, it feels earned.
That kind of character arc isn’t easy to pull off.
THE CHARACTER CHEMISTRY
So I asked Joel Courtney what the biggest challenge was in building Mason and portraying that gradual emotional growth. I also wanted to know how he and Bailee Madison approached showing two people changing over the course of the film, because by the end, they’re very different from the people we met at the beginning.
And for Andy, I wondered how hard it was to capture it.
Joel said, “One of the biggest things that I always try to give a significant amount of my attention to is where we are in the script, what’s happened previously and where we are we headed towards. Films shoot out of order, it can be tricky to keep your character’s growth consistent across the script timeline. And it can’t be across the shooting timeline because you’re filming out of order, right? That’s always been something that, not always something that I’ve gotten right.”
He then added, “When I was a younger actor. It was not something that I realized was important when I was just figuring out what I was doing. And so to this day and for quite a while now, it’s the thing that I give the most attention to because you can see the characters start to fall in love with each other a bit more every time. It’s not like, oh, he likes her less here and more there. There’s complications in circumstances and like he’s hurt in these moments, but it’s not that he loves her less. And so Andy really was helpful keeping us on track with that too.”
One thing I noticed while interviewing Joel Courtney and Andy Delaney is how naturally they play off each other. A lot of interviews feel like two people taking turns answering questions, but with them it felt much more like a conversation.
They were genuinely listening to each other.
When one person started answering, the other would jump in to add context, expand on a story, or build on a point rather than repeating it. That dynamic made the interview feel richer because every answer kept evolving, and it gave a clearer picture of how collaborative the movie was behind the scenes.
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BLOCKING
It also says a lot about their working relationship. You can tell they respect each other’s perspective and are invested in talking about the film together, not just promoting it individually. As an interviewer, those are often the easiest conversations to get lost in because the guests are helping tell the story alongside you.
And honestly, when interview subjects are that engaged with each other, it makes forgetting your questions a little easier because the conversation starts carrying itself.
Andy added, “I pay a lot of attention to body language and spatial relationships of how people lean in or lean back or power relationships in terms of standing and seated. In terms of, you know, relaxedness in the body, I think, or a kind of stiffness. And so things like that I keep an eye on from the point of view of almost like a silent movie. So I think actors convey a lot, and it’s wonderful when, you know, you get characters, you know, actors like Joel and Bailey, but they instinctively would tracking the narrative and the relationship and convey it through body language. And if I felt there was an adjustment, I would give that maybe. But I really love working with blocking, blocking actors and cameras. I think it’s a wonderful kind of underappreciated part of moviemaking.”
Blocking is definitely important but it’s not something that we hear a lot about. Shooting movies isn’t easy – it’s a lot of hard work and the scenes are almost always very technical.
The film did look well rehearsed and effortless. The pacing and the flow just worked really well. So I asked if there was anything that looked really easy to shoot but was challenging in real life.
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Joel said, “It’s a very nuanced relationship film. So there was, there were a lot of scenes that we really gave, uh, I mean, all of the scenes we gave a good amount of attention towards the circumstances they’re going through. But I think one of the biggest, and possibly because it’s one of the longest scenes, is the scene where I’m at Leah’s apartment and I’m spending the night because my power’s out. And we have a very long conversation on the couch and we each share our hearts a little bit.”
CONNECTION
He continued, “We open up and have a serious moment of connection and mutual appreciation for each other. That really is like a moment where things start to deepen on the emotional side. I’d say, uh, you know, blocking that, moving up and down the couch, kind of leaning in, leaning out, yeah, pulling away, taking a drink of water as a way to emotionally retreat a little bit after saying something kind of powerful. You don’t know if the other person’s gonna— how they’re gonna take that, judge you.”
The scene did look really easy and I have to admit that I wanted to go and buy a jenga game to put on someone’s forehead.
Andy added, “And it was at the end of the day, it was a night scene. So it was the end of a long day. So we were all getting kind of tired. And, and as Joel says, it was a long scene and we did it in continuous chunks. We were just— we just let it all play out and then we do it from different angles. And actually, Joel’s completely right. It was all about where am I on the couch now? And I’ve come down here and then she comes down and then I and it was incredibly affecting. I, I love it. I mean, I was gonna— there was one scene at the very last shot of the movie when they’re walking down the street, it’s kind of sunset. Yeah, that was crazy because we had some situations going on downtown.”
SITUATIONS
I was intrigued. He continued, “We did, we had situations. So there was situations behind me of, you know, some guy attacking a Budweiser van, and so that was fun. We had cops trying to sort this. It was behind the camera and they were so good at staying in the moment. Behind the camera it was the Keystone Cops.”
When interviewing, time goes by really fast. My time ends and I say my goodbyes. I am always thankful for the time I am given and this is another interview I am thankful for.
40 Dates and 40 Nights is out now.
