Maybe Someday opens with Jay (Michelle Ehlen), a non-binary lesbian, arriving at the home of her estranged wife, Lily (Jeneen Robinson), for dinner and a movie. Lily asked for a separation to which Jay, defeated by her wife’s desire to live apart for a little while, has agreed in the hope that time will bring them closer together. We meet Jay sitting in her car for a brief moment, catching her breath and her wits before walking up to Lily’s front door. Her eyes are glassy. It’s apparent how hard this is for her. When Lily opens with a smile and a warm, “Hey there! Welcome! Come on in, I’ll give you a tour,” it’s filmed from Jay’s first-person perspective. The sharp contrast between Jay’s palpable sadness and Lily’s pleasant demeanor is simple, relatable and deeply emotional. That realization that someone you love doesn’t love you anymore, that you’ve been knocked down to a different tier in their catalog of social behavior and public faces, is utterly devastating.
That devastation — and recovering from it — is the focus of Maybe Someday, which Ehlen also wrote and directed. The story takes Jay on a journey of self-discovery and redefinition. After leaving Lily’s home, Jay starts a cross-country trip to Los Angeles to ostensibly pursue a professional opportunity but really just to run from the heartbreak. Along the way, she stops in her hometown to stay with her childhood best friend, Jess (Shaela Cook), who is also divorced and now a single mom. Jay and Jess share a lot of history together, although Jess isn’t aware she was also Jay’s first crush. Flashbacks to their youth (with Eliza Blair as young Jay and Cameron Norman as young Jess) establish a complicated coming-out for Jay and the pain of her unreciprocated affections for Jess. It’s a cycle she’s felt trapped in for her whole life.
While in town, Jay meets Tommy (Chad Steers), a stand-up comedian whose hidden pain is masked by a personality that only grows bigger the closer someone gets to him. Tommy is brash, but he helps Jay emerge from her shell a little bit and come to grips with the reality that Lily’s promise to reassess after a few months apart wasn’t necessarily true. Their banter and chemistry as friends allows Maybe Someday to be more than just a story about overcoming a failed relationship. The two of them bond, eventually putting on a drag show together. There’s some tension Jay feels over spending more time with Tommy than Jess, for whom she still feels unreciprocated feelings. Her fun with Tommy, though, doesn’t stop Jay from checking her flip phone each and every morning for new texts from Lily, though. Or from hoping she can return to the way things were instead of heading farther west.
I can’t speak highly enough about Maybe Someday and the choices Ehlen makes throughout her film on both sides of the camera. That first scene described above really sets the stage for the rest of the film, which never loses its focus on Jay’s character and her inner turmoil. Revelations about Lily’s choices during their marriage, as well as the fallout of their split, serve to heighten the sense of loss. The flashbacks, too, really inform Jay’s journey. It helps that Blair’s version of the character is played with as much focus and control as her older counterpart. She’s an imperfect person with a complicated love life. It’s amazing how many other films can misunderstand how to play something so relatable and true. Ehlen kills it.