Aaron Sinclair talks his newest film, modern dating, and being single
It’s February and love is in the air. For some of us, at least. Here comes that special time of the year to remind us who has been struck by Cupid’s golden arrow versus those who have tasted the lead-tipped arrow instead.
Narrative filmmaker Aaron Sinclair puts the audience through the woes of modern dating in his new interactive film, Singleness. Featuring a Saskatchewan-based cast and crew, this film was shot right here in Regina. Readers, beware of light spoilers ahead!
From experience to inspiration
Throughout the 14 years of being a filmmaker based in Regina, Sinclair has explored various concepts in his craft. This time, his personal connection to being single birthed a film that will have those going through post-breakup or looking to find love, be able to see themselves depicted on screen.
‘’I’ve been personally single for a while and just kind of living that life, often [I] find [that] this is a unique experience and it’s [in] the small quiet moments that you notice it,’’ said Sinclair.
The idea of using singleness as a concept had been brewing in Sinclair’s mind for a couple of years. It came into fruition when the app, Choosewise, provided the opportunity for collaboration on the project.
“I actually had shot sort of like a pilot episode before we got the opportunity,” said Sinclair. “Once I got the chance from Choosewise, I wrote the script in the course of a few months.”
In the film, Seth, played by Andrew Valdez, leaves his romantic fate in the hands of the app’s user. The story thrusts its viewers into a tense break-up scene between Seth and his ex. Then, users are immediately expected to make a choice between fighting for the relationship or letting it go. Each choice reveals a scene that many are familiar with, like an awkward first date, feelings of self-doubt, and jitters before making that first move.
Order the pizza, put on the playlist, and feel the feelings.” – Aaron Sinclair
Home is where the heart is
After spending a few months writing the script, the film was shot in June of 2025 with only three days of shooting. The beginning of the film heavily contrasts the warmth of the sunny day, since the breakup happens at the famous patio of Regina’s Skye Café and Bistro.
Fireside Bistro is another local restaurant that enters the scene as the location for Seth’s first date with Paisley, played by Emma Fiorante. Sinclair expressed his gratitude towards these spots in the city that allowed for filming. He said that showcasing Regina and Saskatchewan in his work is something that happens naturally.
“They just let us in after hours and let us do our thing,” said Sinclair. “It always surprises me how many restaurants or businesses will be willing to do that, as long as you tell them what you’re doing and what you need, they’re happy to help.”
Sinclair also notably mentioned his landlord who has granted him access several times to a space for filming. “We actually shot the apartment scenes in the building that I live in. My landlord often lets me use the empty suites for shooting in, so that helps.”
For Sinclair, filming in Saskatchewan is exciting and unique. He says that it gives a great advantage of being independent and still producing quality work.
“You hear stories in bigger cities, you know, that can get short-lived and all of a sudden locations start to cost a ton of money to get into,” said Sinclair. “I think we’re able to do a pretty high level of production quality here that, if you were doing the same level in L.A., it would cost a lot more to do.”
[Singleness] is just an experience in life, and life is better if you can find joy.” – Aaron Sinclair
Directing emotions and giving hope
Describing himself as an empathetic director, Sinclair’s experience with singleness shone in the way he connected with the actors and their roles.
‘’When we shot the breakup scene, there’s a bit of heaviness that I was feeling while [Seth’s ex] was standing her ground,” said Sinclair.
Although the users might experience melancholic feelings from watching Seth traverse singlehood, there are also lighter moments in the film.
“There’s a heaviness [to] getting dumped, but there’s also pride to it because this character is standing up for what she needs. There’s a lot of joy in that and I think that’s important too.”
Sinclair says that the narrative on being single is often portrayed as being the worst thing that can happen, but it is far from his truth. “[Singleness] is just an experience in life, and life is better if you can find joy.”
In the film, Seth is shown a year later dancing with glee around his apartment. Sinclair thought this was an important element to bring in and show the audience that they can take the reins of their lives.
Sinclair wishes for the audience of Singleness to see their experience represented on screen and to send it to someone who might get a laugh or a tear out of it. At the time this conversation was conducted, Sinclair was aware of Valentine’s Day being on the horizon and hoped that those who see themselves in Seth will treat themselves kindly. “Order the pizza, put on the playlist, and feel the feelings,” said Sinclair.
He also noted that there are many filmmakers in Saskatchewan who are trying to produce interesting and cool films that are worth paying attention to. Currently, Sinclair is in the early stages of working towards his next feature film. He says there is already a script and he is starting to bring people in to get the ball rolling. In the meantime, and after bonding over dating traumas with Seth, one can catch Sinclair’s other interactive film on Choosewise, titled Awake. To view his other works, visit @aaronsinclair.film on Instagram.
