Filmmakers John Mitchell and Christina Zeidler are proud of their Canadian roots, wasting no opportunity to name drop neighborhoods to make it abundantly clear that Portrait of a Serial Monogamist takes place in Toronto. It’s something New Yorkers have been doing this for ages now with their city, so at least this film offers a perspective on a different area (though the proximity is fairly close). The film also presents a different take on the typical rom-com, as it features a middle-aged lesbian who’s a serial monogamist with a long history of broken hearts. Some of the gambles in the film don’t pan out, like needlessly breaking the fourth wall by speaking directly to the camera, but without risking failure, you’ll never attain success, a lesson that the central character soon learns the hard way.

Elsie (Diane Flacks) has been a serial monogamist since grade school. Now, as forty-something lesbian, she’s practically an expert at breaking up with existing girlfriends and starting new relationships. Yet when Elsie breaks up with her girlfriend Robyn (Carolyn Taylor) of five years, she uncharacteristically finds it difficult to move on. This is strange because Portrait of a Serial Monogamist opens with a monologue of Elsie confidently giving advice on how to properly break up with your partner, even ending her spiel with “after you’ve made your decision, never look back.”

Unable to take her own advice, Elsie seeks opinions from close friends on how to cope with being single again. Her first instinct is to listen to her friend who suggests she immediately start dating. In the best scene in the film, her friend Sarah (Sabrina Jalees) explains how the holy grail of the dating world is the dog park. Sarah insists that you can tell a lot about a potential partner by the breed of dog they own—she recommends staying away from owners of black labs and retrievers as they are loyalty breeds and stick to owners of more free-spirted breeds, like cocker spaniels and terriers. Due to Jalees’ comedic background, this scene plays out with a ton of laughs, but it’s also clever. In the same vein as the famous car door lock advice from A Bronx Tale, Sarah warns, “if anyone tells you their name before the dog’s name, run.”

But most of these shoddy suggestions just feed into her old ways of thinking. It becomes frustrating to watch her struggle between a younger new fling (who hardly seems promising) or her former long-standing lover Robyn. Several flashbacks throughout the film that indicate how much Elsie still thinks about Robyn, making it obvious to everyone except for Elsie that she should get back with her. Which leads to the biggest issue of the film—not getting a chance to properly value the relationship that the film is centered around. Because Portrait of a Serial Monogamist begins with Elsie immediately dumping Robyn, it’s difficult to feel the impact of why she was so important to Elsie.

Mitchell and Zeidler provide some valuable insight on how heartbreak and love go hand-in-hand, and how trying to avoid one will result in losing the other. But in the end, this light-hearted indie comedy suffers from stiff performances (aside from Jalees, who could have used some more screen time), and an abundance of subplots and clichés. At least Portrait of a Serial Monogamist follows the (eventual) advice of its characters by attempting to provide fresh ideas from a unique vantage point, even if it doesn’t completely succeed.