The impediment that a contemporary romantic comedy is faced with isn’t extreme social taboos or audience sensitivity, but the baseline justification for why two characters would meet one another. It’s not that rom-coms are subjected to being “cancelled,” but that they’ve become a lot more boring when online dating apps are the most frequent spark for relationships; without a stranger-than-fiction true story like Hit Man or a high concept premise in Palm Springs, these modern rom-coms struggle to differentiate themselves because they’re interchangeable on a narrative basis. The requirement of a “hook” is something that Voicemails for Isabella’s writer/director Leah McKendrick is aware of because there’s a near-constant series of references to Sleepless in Seattle, a decision that’s either aided the film’s self-awareness or subjected it to untenable comparisons.
The internet had made a meal out of determining which classic rom-coms are “creepy” today, even if that was often acknowledged at the time. It’s to the credit of Voicemails from Isabelle that there’s an acknowledgement of how manipulative the set-up is; the culinary student Jill (Zoey Deutch) recently lost her sister Isabelle (Ciara Bravo) to cystic fibrosis, and has coped with the loss through the recording of messages sent to a cell phone number she believed was unlisted. The voice memos Jill made for Isabelle were directed to the number of the real estate agent Wes (Nick Robinson), who’s made to feel more self-conscious about being single after his best friends (Harry Shum Jr. and McKendrick) get engaged. Jill has worked in San Francisco, but Isabelle and her parents (Gil Bellows and Tanis Dolman) are from Austin, which is where Wes is located (explaining how the number could get redirected). Wes has received these messages and begun to fall in love with the firsthand knowledge he has about Jill’s life, but it’s not until they meet that he’s informed that Isabelle’s dead.
On a foundational level, Wes is obviously in the wrong because he could’ve let Jill know that she wasn’t sending messages to a non-existent number, and he definitely should’ve backed off upon the realization that they were intended for a deceased sibling. Yet, this is a rom-com that also has an impromptu tour bus hosting gig and a Robyn dance number, so there’s some whimsy that can be applied. Wes isn’t framed as manipulative because the coincidence of the film is the only reason that two people of their generation would be willing to open up to one another. Even in a seemingly more connected world of digital dating, it’s unlikely that Jill would ever meet someone new with whom she’s able to openly discuss her feelings of remorse and anxiety. Grief is a crutch that she’s used to justify not taking initiative, but it’s also the only real thing that Wes has heard because his profession is based on spinning information in a positive direction.
It’s stark to compare how little the film is interested in Wes’ background, given that there’s no information about his family, but Robinson’s willingness to show overwhelming enthusiasm in impromptu moments. This would imply that the character has never had a circle of people who he can be vulnerable around, even those played by Schum and McKendrick. Similarly, Deutch is able to add a touch of narcissism to Jill so that she doesn’t come off as an unambiguous victim. Years have passed since her sister’s death, and she’s used it as an excuse to be conservative in the pursuit of her career ambitions. That doesn’t mean that either character is unsympathetic, but that there’s something they might pick up on from having an honest conversation with someone outside of their insular friend group.
The issues that arise are due to tonal miscalculation. The film’s first 20 minutes get into the last days of Isabelle’s life and the blow it caused Jill, who’d used her sister as an idea springboard. Deutch’s acting is good, but it’s far too dour for a film that also has a number of over-the-top side characters, such as Nick Robinson as Jill’s grumpy boss Chef Bastien. There’s also an unnecessary appearance by Jill’s would-be romantic partner Tyler, played by British gold medalist sprinter Toby Sandeman, who’s a professional dating podcast who doesn’t practice the same lessons that he’s preached. Perhaps the intention was to have an example of what a manipulative potential boyfriend would look like so Wes can only be an improvement in comparison, but rom-coms would improve if they dropped any references to podcasting that are bound to age like milk.
Deutch was funny in this summer’s slapstick comedy Gail Daughtry and the Celebrity Sex Pass, but her work here is closer to the casual affability that she showed within her collaborations with Richard Linklater. Robinson’s been on my radar since his youth breakout performance in the coming-of-age adventure Kings of Summer, and he’s been positioned as a rom-com lead several times since; Voicemails from Isabelle is not only the best, but a sign that he’s an adult actor who’s moved past the moody teen phase.
Voicemails from Isabelle is highly watchable and could’ve played in theaters, which isn’t something that could be said of a lot of Netflix originals. The one barrier is its length of nearly two hours, which is too long for something with such a straightforward premise. Sleepless in Seattle was only 100 minutes, and Deutch and Robinson aren’t Meg Ryan and Tom Hanks.