Iris DelaCruz (Hera Nalam) mistakes Simon Friesen (Kristian Jordan) for some other guy she met at a part once. I suppose this counts as a meet cute. Since they’re already talking, she asks him out for a drink. They go to a bar. There, Iris and Simon reveal each other’s secrets and decide to never see each other again. For a while, this works. With I Propose We Never See Each Other Again After Tonight, director-writer Sean Garrity shows their separate lives.

Simon works with Gord (Matthew Paris Irvine), who proposes that they appear in a porn. Gord promises to be respectful during shooting, but Simon shoots him down before their boss tells them to go back to work. Iris, on the other hand, tries to live her life as a 1.5 generation twenty something Filipino Canadian. She’s also helping her family plan her sister’s wedding. But she looks out of the window, signaling that she wants to see Simon again. Separately or together, Propose at least shows how beautiful Winnipeg is.

Comedies like this are always about its side characters. For a while, I see potential in how I Propose builds them. It gives to time show Gord’s fleeting interests, and it also shows Iris’ task oriented future brother-in-law Justin (Aaron Pridham). But then those characters just end up being the worst. Gord turns out like one of those gay characters who try to manipulate their straight male friends. And I mean we all manipulate our friends but not for a kiss. Iris’ sister Agnes (Andrea Macasaet) is just as bad. She tells the former that she can’t just sleep with two men her entire life. This advice sounds like it’s coming from a bad friend instead of a younger sister, and it encourages unnecessary drama.

The Filipino Canadian culture also gets misrepresented here, as it highlights their shame in Iris, a divorcee moving in with another man. Sure, that’s an issue, but it’s a bigger issue that they haven’t met Simon to figure him out. Filipino-boyfriend relationships can go many ways, but The introduction part is essential here. People of any ethnicity introduce serious partners to their parents. Also, Simon being white makes Filipino families less judgmental. Lastly, I’m happy for Filipino representation in Canadian cinema. This is apparently the first Canadian film to do so, and firsts are always rough. But I wanted to see Simon’s Mennonite family too.

Eventually, Iris and Simon move in together after a three month relationship. She confesses to a betrayal that makes him walk out on her without his shoes on. Iris drives to his home town to look for him instead of, you know, looking more closely. This is just one of Propose‘s many third act contrivances. Sure, love can make a brown woman drive to a town that’s full of white people but it doesn’t address that fear. This walkout also hints to Iris and Simon being neuro-atypical, another issue that Propose fumbles on.

Love conquers all but not my suspension of disbelief. This search, by the way, is one of many scenes showing Iris or Simon’s search history or texts, which do not look good on my roommate’s 40 inch screen. If those search histories are important to the story, the least a filmmaker can do it let us see them. Nalam is a singer who’s acting for the first time. She eventually gets to sing here, highlighting a good poppy soprano voice. She’s also a good actress, and there’s an honesty when she and Jordan are together, but that’s not enough to save this mess.

Also Iris and Agnes’ mom wears blue eye shadow which no.