Ryan Reynolds’ career has been defined by snarky detachment. Since his early days as Van Wilder, the Free Guy star has built his onscreen persona around an ability to wink at the material he’s playing—a skill he took to its logical extreme in Deadpool. But the truth is that it can often be easier to deliver subversive commentary than to do a well-worn genre right. That’s especially true for romantic comedies, which have tropes so familiar and missteps so mockable that the parodies practically write themselves. It’s not hard to score points with a deconstructed rom-com. What’s rarer and more special is when a romantic comedy can breathe new life into old formulas without throwing the rest of the genre under the bus. And back in 2008, an unassuming Reynolds vehicle managed to do just that.
Definitely, Maybe has a depth of humanism that’s both surprising and refreshing, especially for a studio rom-com made as the genre headed towards its nadir. Romantic comedies are always trying to walk the tightrope between evoking real-world experiences while still keeping things light and comforting. And writer/director Adam Brooks gets that balance just right, partially through his understanding that the two most precious commodities in a romantic comedy are time and empathy. So his film unfolds across 16 years of plot, as life, love, and work intersect in a world in which there are no “right” or “wrong” love interests, just flawed people trying their best.
Plotwise, Definitely, Maybe is essentially How I Met Your Mother with a dash of High Fidelity. Reynolds is Will Hayes, a late-30s political consultant turned advertising exec on the verge of a divorce. When his 10-year-old daughter Maya (Abigail Breslin) comes home from school with some lingering questions about a sex ed class—not to mention an ulterior motive of trying to get her parents back together—she asks her dad to tell her the story of how he met her mom. Will agrees but decides to change the names and details in order to spin a “love story mystery.” So Maya is left to guess which of three very different women from Will’s past might be her mother: sunny college sweetheart Emily (Elizabeth Banks), adventurous nonconformist April (Isla Fisher), or confident, cultured writer Summer (Rachel Weisz).
That means Definitely, Maybe’s narrative unfolds on two different levels. On the one hand, it’s a classic coming of age tale for Will, whose story starts when he arrives in New York City as an idealistic staffer for the 1992 Clinton campaign. On the other hand, it’s also the story of a kid first starting to realize that her parents are complicated people with their own messy humanity. There are moments when Maya struggles to wrap her head around the idea that any of the flawed young women Will describes could possibly be her responsible, loving mother. It’s hard enough for her to handle the news that her dad used to be a smoker.
Will’s smoking habit is an early sign that even though Definitely, Maybe has a glossy studio sheen, it hasn’t been entirely sanitized. Smoking is one of those common habits that’s been weirdly erased from 21st-century rom-coms, the better to paint a rosy, clean-cut picture of the world. But in Definitely, Maybe, it’s one of the first things that Will and April bond over, as they bet on whose preferred brand of cigarettes will burn faster. Though the film only intermittently engages with its ’90s setting (and not at all in its costuming), the cigarettes are the sort of authentic detail that goes a long way towards making its world feel real.
It also helps that Definitely, Maybe isn’t a “soulmate rom-com” about how there’s one perfect person for everyone. Instead, it looks at the realistic ways in which timing, circumstance, and miscommunication can impact and upend relationships. And it finds hope in the fact that good things can still come out of a romance that’s not meant to last. Definitely, Maybe is essentially the cinematic equivalent of the adage that people come into your life for a reason, a season, or a lifetime—and that there’s value in all three. Brooks sees love as a journey, not a goal. And that allows him to pull off a much more successful version of the same sort of twist ending that How I Met Your Mother biffed.
While How I Met Your Mother stretched out its story too long to make its pre-planned ending land, the power of Definitely, Maybe is in its ability to elegantly collapse time. The movie weaves a decade and a half into two hours, which gives its rom-com arcs a unique poignancy. At times Brooks zooms in on the nuances of a specific hurt, like a brutal fight that drives Will and April apart for years. But he can also zoom out to capture the way that time shifts our perspectives too. In one scene, Will and Summer have a quietly devastating break-up over a conflict of interest in their respective careers. The next time we see them together, however, it’s a few years later and the old hurts have softened into a nostalgic desire to turn over a new leaf of friendship. The movie offers savvy insight into the way that time can, if not heal all wounds, at least cushion them quite a bit.
Definitely, Maybe also resists falling back on reductive love triangle clichés. While rom-coms with multiple female leads often pit them against one another in order to use the flaws of one character to argue for why another is the “right” kind of woman, Definitely, Maybe eschews that entirely. It’s part of what lets the movie pull off its genuine sense of suspense and surprise. You could see Will being happy with any of these women. And though the time-jumping premise leaves a lot of gaps in the characters’ onscreen lives, Banks, Fisher, and Weisz make up for that with the three-dimensional humanity they bring to their respective roles. Definitely, Maybe strikes a nice balance between delivering lived-in specificity and leaving space for the audience to project some of their own details onto the story too.
For his part, Reynolds turns in one of the sweetest, warmest performances of his career. Though he would go on to have a bigger rom-com hit opposite Sandra Bullock in The Proposal the next year, Definitely, Maybe is easily his best work in the genre—far more so than the Van Wilder schtick he used to paper over the toxicity of Just Friends. As Will grows up, his youthful idealism stagnates into pragmatic acceptance, and Reynolds captures both sides of that coin without falling back on any of his usual bag of deadpan comedic tricks. He’s playing an actual character, not just a snarky persona. And particularly from the vantage point of 2021, there’s an intriguing meta layer to watching Reynolds portray a guy whose romantic ups and downs feel like a metaphor for the actor’s rollercoaster career through Hollywood.
Though Definitely, Maybe did okay at the box office and got a decently warm critical reception, it isn’t a movie that’s particularly stuck in the cultural consciousness—perhaps because even the best rom-coms of its era were generally met with a base level of scorn. While Reynolds was able to ditch the faltering genre and (eventually) find success in the superhero one instead, Definitely, Maybe’s creator hasn’t been so lucky. Brooks seems to have faced the same problem that a lot of would-be leading ladies did in the 2010s: The type of movie he was best suited to making was no longer in fashion. Brooks has yet to direct another film since Definitely, Maybe, although he did co-write the 2018 Sanaa Lathan Netflix rom-com Nappily Ever After (and create Bravo’s dark comedy series Imposters).
It’s a shame because Brooks has a real knack for injecting originality into the rom-com template without looking down on its cornier tropes. Most importantly, he understands that a good rom-com isn’t just about romance. In Definitely, Maybe, Brooks has an interest in relationships of all kinds, including Summer’s strange co-dependent bond with aging cad Professor Hampton Roth (Kevin Kline) and the complicated interpersonal ecosystem of Will’s fellow campaign staffers. Most poignant of all is Will’s relationship with Maya, and her slow acceptance of the fact that her parents aren’t meant to be together. At this age, Breslin was a master of playing kids struggling to process complicated adult emotions, and she puts that skill to great use in the movie’s emotional climax, as Will emphasizes that she’s more important to him than any of his romantic relationships.
As Reynolds’ career continues to climb in the wisecracking action-comedy direction, Definitely, Maybe is worth seeking out—both as a good rom-com from a bad era for the genre and as a solid application of the actor’s charms. It’s optimistic without being unrealistic and sweet without being completely saccharine. It’s a movie that’s aware of rom-com tropes but doesn’t worry too much about winking at its audience. Definitely, Maybe isn’t just set in the 1990s; it calls to mind the best of what creators like Nora Ephron and Richard Curtis produced during that era. And it proves that sincerity can be just as entertaining as snark.
Next time: There’s no replacing She’s All That.
