Cinema may be fluent in the language of romance, but breakups are another, excruciating story, and Christian Frei is happy to chronicle them in “Sleepless in New York.” Following three lovelorn city dwellers over an extended period, Mr. Frei’s raw documentary plumbs the soul-searching, pain and dark, obsessive thoughts that afflict these victims of lost love.

Each of these romantically bereft creative types brings a different shade of anguish to the table. Alley Scott, a multitalented designer, is freshly dumped by her partner of several passionate years. Her fair skin is often flushed from crying and appears all the more blotchy in frequent Skype footage. For Michael Hariton, a translator, the sting comes from the casualness with which he was dropped, on the way to drinks; he lends a caustic, self-lacerating perspective, with the expression of a dog fearing another beating. Finally, the burlesque dancer Rosey La Rouge lives in a what-if world, pining for a man she met once in costume at Coney Island.

A running thread in the film, quite literally, is Helen Fisher, a biological anthropologist who studies the basis of romantic feelings. Often shown jogging or observing human mating rituals at a bar, she’s a strident, repetitive proponent of the view that love is an addiction, an opinion that quickly acquires the ring of a self-help talking point.

Mr. Frei adds to the medley of misery with warped shots of subway riders and their imagined musings. There’s something woebegone about the film itself as it staggers along, ever in danger of tipping into the abyss inhabited by one of its subjects.