The quietly composed film Maybe Someday follows Jay, a photographer recently separated from her wife, on a journey away from her old life and towards a new and unmapped path in Los Angeles. On the way, she visits a high school friend, once (and perhaps still) a BFF, and a divorced mother Jess.
In a sense, Maybe Someday is Jay’s road trip tale, travelling somewhere else in her own melancholy mind. Bereft and nearly expressionless, she hesitantly texts her ex (on a flip-phone), sending and receiving fairly meaningless messages that tether her to an obviously defunct relationship. With Jess, she has a halfway safe haven, geographically and metaphorically, to her destination.
Through flashbacks, younger versions of Jay and Jess are shown as quintessential teenage girls in the throes of a passionately platonic friendship, often described as a training ground for later adult romances. Different here for Jay, because for her, it’s not a rehearsal.
Meanwhile, Jay and flailing cynic/comedian Tom team up, first as colleagues and then as pals, giggling at ideas such as breast-milk moisturizers, mortifying poor Jess, who is navigating her own way in a world she never expected to captain.
Altogether, Maybe Someday is a touching film, sometimes uneven and awkward, but as in the portrayals it reflects, people at all ages blossom, one way or another.