With Thanksgiving right around the corner and Christmas not too far behind, a film like How to Ruin the Holidays is a perfect story for those looking to reignite their holiday spirit as our year comes to a close — and offers a timely message on the absurdities of family life around the seminal shifts in perspective we all must face throughout life.
It’s a movie that thoughtfully showcases its all-star cast of comedic actors, keeps nostalgia top of mind, and eventually transforms itself into a love letter to human connection. I had the immense pleasure of sitting with the film’s writer and producer, Kevin Gillese, alongside his collaborator and director, Arlen Konopaki.
The dynamic duo gives an in-depth talk about their thoughts on the holiday season, what it means to make a Christmas “classic,” and how independent filmmaking changed their lives. Take a look at our wide-ranging conversation below:
Let’s let’s start with the holidays. The holidays are this really interesting time for people around the world. Whichever holiday — Christmas, Thanksgiving, Hanukkah, and so on. It’s a period to reflect and reorganize your life. What was it about the holiday season that really drew you both to this project, and how did you approach the emotional behemoth that is Christmas?  
Kevin: I’m a Christmas baby, so there’s a little bit of an extra connection there. After moving away from Canada back in 2010, the holidays became the time when you get these yearly snapshots of your family and friends when you haven’t seen them.
Your updates on them come through strange vignettes. I think I wanted to write from that perspective because it felt true and like something that possessed this bittersweet quality.
On the one hand, it’s always exciting to come home. But, it also heightens the fact that you’re losing a large connection with these folks that you’ve known for so long.
Arlen: I love the holidays. I love Christmas time. The thing that’s interesting about Christmas, and the holidays in general all year round, is that there’s this expectation from an early age that it’s supposed to be magical. It’s about families coming together, forgiveness, love, and the spirit of the season.
This creates this innate pressure to feel all these things, which ironically ends up making it more of a pressure cooker for families and relationships than anything else. It’s an interesting time.
That’s one of the reasons there are so-so many compelling films that are set around these times. There’s something inherently dramatic during the holidays that keeps us all interested.
 That perspective in mind… Christmas movies carry a lot of precedent, and I’m sure that thought process rubs off on the filmmakers trying to tell a good — stand out — holiday story. In so far as movies we consider “classics” of the holiday genre, they have to juggle the nostalgia that audiences expect with an ability to subvert those tropes that made them classics in the first place. How were you both able to capture the nostalgia of those tentpoles, all while bringing something new to the table?
Arlen: In a lot of the best Christmas movies, there is this underlying tension—an ongoing push and pull between comedy and drama. There’s a bittersweetness to them and also an overwhelming level of nostalgia.

 
“I think people at the holidays want to watch something that is either comforting or reflective of the thing they’re experiencing at the time…”
I think people at the holidays want to watch something that is either comforting or reflective of the thing they’re experiencing at the time, which in some ways made our movie thematically easy.
Kevin wrote a great script that has a lot of those familiar feelings for families. Whether it’s the sibling that really bothers you, the feeling that you’re disconnecting from a parent, or the desire to have things be the way they were when you were younger.
All those themes were present in his script, and it was just about making sure that they were portrayed honestly. The comedy is going to be there and the drama is going to be there, and there’s going to be a lot that people can tap into.
Of course, one of the things that excited me about this project from the beginning was that the best Christmas movies, more than any other genre, are watched every single year. If you can make one that can even approach the quality of some of those great classics, you’re going to be watched every year forever.
That was always really exciting, trying to make something as close to a Christmas classic as we could, and that was always the goal. No pressure.
Kevin: My favorites are ones that really subvert the genre in significant ways, like Bad Santa, right? Or maybe to go back further, Scrooged or Love Actually.
Those movies work because they see the trope, present the trope, and flip it on its head. Then, they come back to their audience and flip back to the trope again.
I love that there’s a very comedic sensibility to that kind of reversal. See the trope? Just kidding. This isn’t a Christmas movie. It’s totally different. Actually, just kidding again. It was a Christmas movie all along.
Arlen and I have been a comedy duo for many years, so that’s the language we both speak. That was our way “in” to making something that was earnest.