The title of writer-director Ilya Chaiken's feature debut Margarita Happy Hour refers to a regular gathering of five women who met as young New York art punks, and have remained friends as they've become welfare mothers, approaching middle age. They get together with their kids at a nearby Brooklyn Mexican restaurant, and sip rainbow-colored margaritas while commiserating about their declining sex drives and their difficulties in qualifying for Medicare. Eleanor Hutchins plays the most apparently centered of the bunch, a freelance illustrator who makes her money drawing busty babes for a pornographic magazine. But, then, she doesn't need much money, since she splits the rent on her house with a bunch of fellow bohos, including her responsibility-dodging boyfriend (Larry Fessenden), the father of her toddler daughter. Hutchins' routine gets upset when she takes in an old friend (Holly Ramos) who's recovering from a recent drug overdose. ("My boyfriend found me in the backyard, dead," she explains.) As Ramos needles Hutchins about her ramshackle domesticity, the artist/mom reflects wistfully on the woman she was. Chaiken handles the resulting flashbacks cannily, often cutting back and forth between a location and the same spot a few years earlier, showing her lead literally looking at her former self. Chaiken also has a knack for the subtleties of dialogue, demonstrated in the way she has a government official spell the tricky last name of a man on the waiting list, or how Fessenden registers his disapproval of Ramos' presence by grumbling to Hutchins, "You have this way of making little decisions that somehow affect my entire life." Margarita Happy Hour takes place in a notably fleshy milieu, where a stressed-out woman confesses that she cries while watching sitcoms, and a man agrees that it's an honor that Iggy Pop once wanted to have sex with the man's lover. The trouble is that while Chaiken's community is nuanced, it's not exactly a warm, inviting place to spend time. It's dingy and dismal, and though not exactly humorless, Margarita Happy Hour misses many chances to be funny, at times when a laugh or two would open the picture up. The entire structure of the plot points to tragedy, and the weight of that inevitability becomes trying. Nevertheless, Chaiken's promise shows in moments that demonstrate a clear eye, such as when Hutchins meets with her pornographer boss, and can't stop chuckling at the juxtaposition of the photos of bare breasts on the wall behind him and the droplets of milk that cling to his mustache.