Everyone in Anne Wheeler’s Better Than Chocolate (1999) is on the precipice — or squarely in the middle — of a transitional period; nearly all of its narrative strands unfurl kind of like miniature coming-of-age films for people having a second puberty. At first it seems positioned to be a rather straightforward romantic comedy that’ll chronicle how things will play out between young women who fall in love basically as soon as we’re introduced to them. They’re Maggie (Karyn Dwyer), a 19-year-old who’s prematurely dropped out of college to work in a lesbian-centric bookstore run by the charmingly stern Frances (Ann-Marie MacDonald), and Kim (Christina Cox), who’s a little older and lives itinerantly out of a school bus spray-painted with nude female forms. The universe cajoles them into living together nearly as quickly as they meet cute: Kim’s mobile house is towed around the time Maggie secures a cushy subletting opportunity.

The two can barely enjoy the heaven-on-Earth pleasures of a new romance — best encapsulated in Better Than Chocolate by a cornily soundtracked montage where they paint each other with sewage-evoking colors and plop onto floor-bound canvases to capture their fresh coupledom for posterity — before everything is upended. Maggie’s housewife mother, Lila (Wendy Crewson), has filed for divorce from the husband she’s just discovered is unfaithful. She’s hoping she and Maggie’s teenage brother, Paul (Kevin Mundy), can crash until she figures things out. Maggie agrees despite her apprehensions. Aside from being an all-around nag critical of everything from her clothing to her professional explorations, Lila doesn’t yet know that her daughter is a lesbian, an identity Maggie is still getting used to post-college. 

Better Than Chocolate makes us see Lila just as frustratedly as Maggie does. It also has true empathy for her, lamenting how she gave up any aspirations she might have had — she studied opera in school — for a marriage that ultimately didn’t work out. But it lets her have some fun in rediscovering herself. One of the film’s funniest sequences sees Lila discovering a dildo- and vibrator-stuffed box under Maggie’s bed and, after a few seconds of shock, going to town with them herself. Paul will have a sexual awakening, too; he’s shown some ropes by a sexually assertive young woman who frequents the bookstore where Maggie works.

Written by Peggy Thompson, Better Than Chocolate is careful not to spend more time with its heterosexual characters than its queer ones; it isn’t very interested in excessively indulging straight viewers. After some time clamping down their passions out of a fear of getting caught, for instance, Maggie and Kim have an outing at a lesbian bar, where they sway on the dance floor and have a quickie in a bathroom stall so audibly steamy that the line of patrons that’s accrued claps when they push open the door with their hair mussed and lips flushed. 

There’s also a burgeoning romance between Judy (Peter Outerbridge), a trans woman who’s stressed about being too forward, and the shy Frances. Better Than Chocolate missteps in having Judy be played by an actor who’s straight and cisgender in real life. The character also marks one of the most positive depictions I’ve seen in a movie of a transgender person. Barring a couple of bigoted interruptions that will be immediately ameliorated, she’s always seen and appreciated for who she is. The film is pointed that the recognition of her humanity shouldn’t be contingent on how palatable her gender identity is to close-minded outsiders. Better Than Chocolate is well aware of, and doesn’t ignore, how its women characters might be seen by broader society. But it never dwells too long on hardship, buoyed by its sense of possibility and optimism.