After a chance encounter leads to drinks and conversation, Iris (Hera Nalam) makes one simple and rather unexpected request of her new acquaintance Simon (Kristian Jordan). During their brief time together, Iris wants them to be completely honest with each other. They will share their secrets and fears without shame because after tonight they will never see each other again. Of course, as is usually the case in romantic comedies, things do not go as planned in Sean Garrity’s latest work I Propose We Never See Each Other Again After Tonight.

While the premise of the film evokes memories of the “now that I’ve met you, would you object to never seeing me again?” scene in Magnolia, Garrity’s film is more of a playful look at two individuals stuck in a self-sabotaging rut. Iris is filled with insecurities stemming from a failed 9-month marriage at age 19, and the perpetual feeling of being the black sheep of her Filipino family. Simon has his own set of doubts, related to his Mennonite past, that keep him from getting to close to anyone outside of his best friend Gord (Matthew Paris Irvine). Although things start off swimmingly for the couple, their budding relationship begins hitting choppy waters when Simon decides to abruptly take a solo vacation to clear his head and allow them to see if they are truly meant to be with each other.

Caught off-guard by Simon’s decision, and encouraged by her engaged sister Agnes (Andrea Macasaet), Iris sets out to embrace her wild side. However, her encounters while back on the dating scene prove far less satisfying than she hoped for. Complicating things further is that realization that, upon Simon’s return home, the pair have drastically different interpretations of what it means to “sow your wild oats”.

As in his previous works, Garrity’s film finds plenty of humour in the idiosyncrasies that often hinder relationships before they truly get started. This is not just confined to Iris and Simon’s romance, but their individual interactions with those in their orbit. The complicated relationship between Iris and her family serve as some of the film’s most richly layered moments. Furthermore, Garrity finds rather inventive ways to convey the modern horror that is the “swipe right” era of dating app.

While I Propose We Never See Each Other Again After Tonight does a solid job of building up Iris and Simon’s bond in the first half, it struggles to balance their individual problems in the latter sections of the film. Since so much emphasis is placed on Iris’ growth, and the lengths she goes in hopes of smoothing things over with Simon, the natural conclusion the film reaches feels a little too one-sided. Simon spends so much time consumed by his own ego and inclinations to flee at the mere notion of discomfort, that his supposed growth is never fully justified. His one big gesture never feels on par with the effort that Iris puts in throughout the film.

Simon’s arc simply needed more depth. For a man who claims to have bedded many women, he seems devoid of any basic understanding of them. Walking around like a zombie in key moments that could have provided hints of personal growth, it quickly becomes apparent that everything we learn about Simon comes from Iris’ inexplicable quest and not the young man himself.

Despite the uneven nature of the narrative, Garrity’s film benefits from the solid performances of its two leads. While Kristian Jordan brings an everyman charm to the film, it is Hera Nalam who delivers a sensational breakout turn as Iris. She is the heart and soul of the film and brings a delicate mixture of vulnerability and inner strength to the role. I Propose We Never See Each Other Again After Tonight is not as cohesive as Garrity’s other films, but the performances keep one engaged as it travels down some rather rocky paths.