The backstory alone is unlike anything else: filmmaker/musician Sook-Yin Lee and cartoonist Chester Brown were in a romantic relationship back in the '90s, and when Lee broke it off, Brown decided to hire sex workers rather than look for another girlfriend — a lifestyle he chronicled in his graphic novel Paying for It in 2011. Now, the adaptation of that graphic novel has been directed and co-written by Lee, bringing the singular story full-circle.
It's a fascinating situation that's just as messy in practice as it seems like it would be a theory. Paying for It stars Dan Beirne as Chester and Emily Lê as a barely-fictionalized version of Sook-Yin named Sonny, and they soft-launch their breakup in the opening scene, with Sonny saying that she's falling for someone else and asking for Chester's permission to pursue that budding relationship.
That sorta-kinda breakup becomes permanent, but rather than moving out of their shared home in Kensington Market, Chester simply drags a mattress down into the basement, where he can hear his ex-girlfriend fucking and fighting with her new boyfriend just upstairs. It's the kind of codependent tangle that seems to make sense at the time.
Chester begins seeing sex workers as a way to fulfill his desires without putting his emotions at risk — something that has moments of sweetness and mostly seems pretty awkward. Paying for It aims to destigmatize sex work, but it's not didactic, preferring to show things as Brown experiences them and not soapboxing about why it's right or wrong. People who don't hire sex workers won't come away from this film feeling like they oughta give it a try.
Even though this story is being told by the people it happened to, it's not overly flattering to its subjects. Chester's transactional approach to sex brings out his superficiality, and when he tells his friends about how great it is, he rarely expresses much overt happiness, often seeming as much like he's trying to convince himself as anyone else. And Sonny is judgemental and fickle, steering their lives into one unsustainable situation after another. They're flawed while remaining likeable and relatable.
It's a wonderfully small, almost uncomfortably intimate glimpse into an odd situation, created with care using lots of Toronto-specific ephemera. Sonny works for a TV station called "MaxMusic" and wears a Mystic Muffin T-shirt, while Chester meets his friends at Buddha Vegan Restaurant on Dundas. There are music video clips from Canadian indie bands like Thrush Hermit, Cub and Gob. Having seen Lee's pandemic film Death and Sickness, I suspect much of Paying for It was shot in Lee's actual house in Toronto.
The film is glimpse into a very specific time and place, when two people who cared about each other made some very surprising decisions in order to maintain that closeness. It's frankly amazing that they were willing to tell this story at all, as Paying for It is a wonderful bit of oversharing that audiences should be grateful for.