“Daddy Issues” is not the laugh-out-loud rom-com it had likely aspired to be, yet it’s just charming enough to make you wish it were better. As evidenced by the dedication card and home movie footage that accompanies the end credit roll, the film appears to have been a meaningful labor of love for Datnow and her sister, Amy, who share both producing and story credits (we are informed in the opening montage that this is a “Datnow Sisters film”). Yet the screenplay wasn’t written by them—Holliday and John Cox served as it coauthors—and the dialogue reads more like a blueprint without the personality filled in. You can almost see the notation “Insert humor here” scribbled in the margins. None of the characters are developed enough to register as anything more than sketch comedy tropes fit for improv exercises rather than a feature-length film. If the film had been funnier, this wouldn’t have been as much of a problem, yet Holliday also wants to convey an important message, and that’s difficult to achieve when the world she has constructed lacks believability.
Henrietta’s need to seek the approval of the men she dates stems from the lack of acceptance she received from her father, whose funeral opens the film. This relatable conflict would’ve had more dramatic heft if the father were portrayed as a human being rather than a stuffy cartoon caricature. He materializes as a disembodied voice that sounds like a mustache-twirling stock villain no less artificial than the series of fools Henrietta chooses to date. It’s glaringly obvious from the get-go that her one decent match is Nolan (Tanner Rittenhouse), her father’s longtime employee whom she finds still living in his dead boss’ house. As per the patriarch’s dying wish, Henrietta treks from London to inherit her dad’s Los Angeles estate, while ensuring that his business remains intact. Yet her designated role on the board requires zero responsibilities, and since she has zero qualifications, the nonsensical speech she delivers—into a pencil, which she treats as a microphone—earns her the expected roundup of bewildered expressions from her father’s colleagues.
It’s a shame that the plot is so formulaic, considering the sheer unpredictability of its leading lady. Datnow has a penchant for slipping biting remarks into otherwise banal interactions and throwing off a secretary by ringing the bell on her desk for no particular reason, all without rupturing her pokerface. She deserves better lines than, “Wanna play with your balls?”, which serves as verbal foreplay to a sexually charged game of ping pong with Nolan. Rittenhouse has an effortlessly likable, easygoing screen presence evocative of Paul Rudd, yet even that can become grating as his stunted maturity tests the patience of his girlfriend, Grace (Martha Hamilton), a single mom whose exasperation is entirely warranted. Henrietta and Nolan’s eventual romantic pairing is such a foregone conclusion that it makes the long progression toward them realizing this fact all the more tedious.