Nobody can claim to be immune to the power of decades of film which have seen glorified, unrealistic and so-called perfect versions of love pushed upon us. Thankfully filmmakers these days have and are continuing to evolve and now offer us richer, more vibrant and frankly vastly more interesting perspectives on love as evidenced in William Kenton’s new comedy short Outdoor Seating. When Kenton, co-founder of the Lisa production company, was deep in discussion about the trajectory of the film with actor and collaborator Chloe Troast, who plays protagonist Claire, they were drawn to the all too well known trope of the manic pixie dream girl and the focus on how when dating, we all too often pretend to be something we are not. Over three frantic shooting days in New York, Kenton and his team brought to life their most fantastical yet very real tale about managing expectations and the sheer volume of BS we are all expected to put up with in life. As Outdoor Seating premieres on the pages of Directors Notes, we speak to Kenton about challenging dating tradition preconceptions in the script, keeping nimble whilst shooting to prioritise the performances and creating a soundtrack which delectably clashes with the narrative playing out on screen.

Please tell us who or what inspired this quirky anti-rom-com.

In 2022 I brought Chloe Troast, who stars in the film, a script about a young couple that gets into an argument while installing their window AC, drops it on a baby in a stroller below and then calls her character’s mom, a corporate lawyer for advice instead of going downstairs to help. It was absurd and kinda snarky like a lot of things I’d enjoyed making at the time and Chloe challenged me to try either going all the way or writing something real, and we both agreed the latter would be more interesting to do together. We talked about the urge to become the manic pixie version of yourself on dates, denial and BK boys whose fashion Chloe described as a “bro in sheep’s clothing”. I wrote the opening scene in Central Park and then I got excited about jumping ahead in their relationship to them meeting up as exes, almost going through the motions of a date without the romance but still the attraction.

I often look for the point of stories so the full life cycle of the relationship was meant to add perspective.

Dating is constantly evolving but we definitely seem to be in a particularly bizarre era, why do you think people are engaging with these types of stories?

I think people might have different hopes for dating and new slang lifted on top, but it’s all the same will-they-won’t-they fun! I think there’s been a lot of progress and it’s exciting to try to free yourself from tradition and oftentimes lose your balance. I read the book On Marriage by Devorah Baum, and there’s a quote from it that stuck with me: “A cynic is a romantic trying not to be.” When I saw that I knew it was true, and got so bummed that I had to figure out what it meant.

I love the condensed but additionally expansive way you have pictured their relationship. Tell us about the script writing and development process after coming up with the initial idea.

It seemed like a fun challenge to show the contrast between an adventurous first date and the reality of the relationship sinking in later, and then even later to the wicked flirting as exes. I think I’m just pretty literal and I often look for the point of stories so the full life cycle of the relationship was meant to add perspective. It’s tough to squeeze all of that into a short without losing stuff that you’re attached to.

Outdoor Seating is peppered with modern tropes, cliches and a lot of the standard BS we hear through modern day dating, do those elements stem from personal experience? How did you make it feel so authentic?

It’s a combination of a ton of things I’ve watched, talked about, read or experienced for sure. Very early on Chloe and I talked about going on dates where you feel compelled to become a version of yourself you’ve never met before. The story isn’t autobiographical but it is based in the truth of some of my experiences, like meeting back up with your ex after some time and ignoring red flags so you can believe the version of the relationship you want to be true. There was also the idea of portraying a character like Justin, a “bro in sheep’s clothing” as Chloe put it, that seemed kind of modern and interesting. It was challenging to write and work through my own attachments and biases but after shaping it in the edit I feel like we did get it to a place where it says something about filtering the BS of modern dating and discovering the agency you have to let someone go, and how empowering that can be.

Was the dialogue completely scripted or was there some improvisation during the shoot? I’m thinking of some of the brilliant little lines such as “I want to rent”.

We shot the whole thing in three days so there was only so much time. It was all scripted and then rehearsed and rewritten but I definitely leaned on Chloe and Ryan Leader’s comedic skills on set to discover some giggles and authenticity. During the actual ‘date’ scenes we let the cameras keep rolling and had Chloe and Ryan just talk to each other, as if they were really on a date, like the rent line was written, but the “polyamorous cyborg” was Chloe and Ryan riffin.

It was challenging to write and work through my own attachments and biases.

There must have been some challenges posed by shooting for three days in and around central New York.

The shoot itself was three packed days bouncing around Manhattan and Brooklyn. We started at the Cloisters and had good permit juju that carried throughout the set. Alex Wohlin shot it with two Sony FX3s so we could be more nimble (tight apartments and free streetlight keys) and prioritize the performances we captured while Ryan and Chloe were both together in New York. After wrapping somehow Chloe and Ryan still managed to get up in front of a crowd Friday night at our production company Lisa’s live sketch show.

I really want to put Ryan Leader’s character’s head down a toilet…is that what you were going for?

Haha for sure. People react differently and that’s part of what’s been interesting screening it around. It was a challenge because Justin had to come off as charming enough that Claire would want to pursue him, but menacing at times to feel real in a way. This dude exists, and he sucks! I had been a big fan of Ryan Leader and had him in mind when I was writing the script. He did these really funny sketches that I thought said a lot about dudes in our generation with very little actual dialogue. His email was in his bio so I sent him a script, and he was into it. It was very fun working with Ryan to try and put together this kind of guy and he really brought him to life in a nuanced way. I think you have to be graceful with your judgement of yourself and others’ mishaps but also understand they’re not mishaps if they just keep getting repeated.

How did you evolve the vintage, classic almost rom-com look of the film?

I was trying to keep things simple, restrained, and focused on the relationship between the characters, and let that dictate the images. Especially with the date I was excited to just park the camera and commit to what I wrote and what we got on the day. Alex Wohlin shot the film, and he says, “Everything was informed by the performances, and allowing space in the frame for the actors to work and try things.” It wasn’t easy covering everything in the time we had, but Alex has a fantastic eye and we communicate quickly, so we made our days. Russell Katz on B-Cam remarks, “There is nothing more beautiful than shooting a babe in his father’s arms.” Then we pushed the colors in post with Alissa Yong, who brought a really lively look to it, especially in the Central Park scenes that hopefully brought it to the ballpark of other romantic comedies set in New York of the early-to-mid 2000s.

I ended up with something I hope more people might be able to connect to, a short about a young relationship, one with big feelings and big egos.

Did anything new come through your edit?

There were a few things to confront in the edit, the first assembly was 30 minutes and as we whittled it down I got a little lost at one point in Claire’s arc. Steven sent a new cut with two pages hacked off the back and that did a lot with a little and it was one of the best parts of the process. I ended up with something I hope more people might be able to connect to, a short about a young relationship, one with big feelings and big egos and a story about a hero that needs to decenter herself: “If someone tells you who they are, don’t try and make them someone else.”

The twittering soundtrack, evoking joy and freedom is a wonderful juxtaposition to the storyline, tell us about this part of the film.

You’re right about the juxtaposition, Ali Helnwein composed the music and he’s a wizard! I think the score is much more romantic than what’s happening on screen, almost as if it’s trying to appeal to our fantasies of what a relationship can be like – which clashes with the reality of what’s happening between the characters.

And finally, what’s next for you?

I wanna shoot a TV pilot about New York dating, great expectations in a crumbling empire. Either that or an ensemble road trip movie.

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