In the purposely anodyne Like Sunday, Like Rain, Leighton Meester plays Eleanor, a woman trying to get back on her feet after losing her waitressing job and breaking up with her boyfriend. She eventually takes a job as a nanny for a wealthy single mother’s son, Reggie (Julian Shatkin), a lonely child prodigy who speaks and behaves more like an adult. Their growing and increasingly off-putting relationship ultimately becomes director Frank Whaley’s sole focus, and any political subtext implying a bridge between social standings becomes a casualty of the film’s limited scope. Despite all the supposed goodwill Whaley wrings out of Eleanor and Reggie’s mutually spirit-enriching friendship, the film evinces a perpetual streak of cynicism. Both the upper- and lower-class milieus from which Reggie and Eleanor originate, respectively, are presented as soulless hellholes populated with either vapid or resentful people concerned only with themselves. Whaley never gives these characters a humanizing moment outside of their default personalities, which turns them into cartoon impressions of the worst of each class (hostile world-hating for Eleanor’s family, stoic unfriendliness for Reggie’s).
Whaley does suggest the twin disillusionment Eleanor and Reggie feel with their background as a means for them to seek solace with one another, but this is essentially the one convincing factor for their relationship, which Whaley, even in the midst of a shared passion for music that’s revealed too late in the film, doesn’t effectively develop further. It’s never understood why the know-it-all Reggie, seemingly content with his loneliness, takes to Eleanor in the first place, since she never exactly teaches him anything and even appears to be less mature than he is (she’s also frequently overruled by Reggie when she suggests that he should be doing activities with kids his age). The one quality of Eleanor’s that Whaley does accentuate is her physical beauty, which is usually captured subjectively as if to suggest this is coming from Reggie’s point of view; the culmination of this occurs in a picnic scene where Eleanor is depicted as nothing less than an ethereal angel. The film’s central friendship thus assumes a disturbing feeling of a blooming romance, and in the process practically recontextualizes the newly single Eleanor’s initial decision to care for Reggie as a truly odd form of rebounding.