Will Hayes (Ryan Reynolds) is a determined idealist. This despite his youthful commitment to Bill Clinton and his upcoming divorce. At the start of Definitely, Maybe, Will is almost painfully cheerful, making his way to pick up his daughter Maya (Abigail Breslin) from school, his head (and the soundtrack) filled with Sly Stone’s bright, propulsive “Everyday People.” Folks on the sidewalk smile into his POV camera and he walks, in slow motion, all good will and hope.
On arriving at school, however, his happy day is dashed: the students have been exposed to sex education and their parents are in a panic. “Do you have sex with daddy?” worries a little girl. Maya is more direct, asking about penises and thrusts and vaginas. “Stop saying ‘penis,’” Will pleads as they head through the foyer, past the doorman, to his apartment. Aha, Maya deduces, if she wants him to do something for her—like tell him the true story of how he met her mother—all she has to do is say “penis” a few more times. She’s not only adorable and clever, but also right.
The rest of the movie, beginning with Maya’s self-arrangement among her pillows and stuffed animals, is dad’s story as she hears it. Maya slides in occasionally by split screen, to perk up the story with whoa-there questions or precocious commentary. She calls it “like a love story mystery,” as Will changes women’s names in order to keep her guessing as to who mom’s identity. First of the three candidates is Emily (Elizabeth Banks), his “college sweetheart” in Wisconsin, with whom he is “deeply in love.” When Will decides that he needs to move to NYC to work for the Clinton campaign, she’s worried that the city will “change” him, but he assures her that she’s the perfect mate, that he only needs to pursue his dream a little bit, and that they’ll be together following his couple of months in the melee of political wheeling and dealing.
As much as she wants the story to be a kind of hybrid surprise, Maya early on comprehends its conventionality. “Everybody knows that the girl at the beginning of the story always gets dumped,” she whines, as pretty Emily recedes in Will’s departing POV shot. In New York, he is provided a roommate-confidante-coworker, Russell (Derek Luke), whose earnest support of the candidate recalls, rather nostalgically, that brief moment when Bill Clinton was deemed “cool” on Arsenio. Sadly, Russ is soon reduced to Will’s advisor, encouraging the good white boy to read through the diary Emily has asked him to deliver to her erstwhile best friend and onetime lover, Summer (Rachel Weisz).
The titillation provided by such reading serves as yet another sign of the boys’ lingering adolescence (Will literally reads under his covers with a flashlight, not exactly endearing). The point is underscored when Will meets Summer and her lover/thesis advisor, Hampton Roth (scene-stealing Kevin Kline). She’s the second option in the who’s-your-mama? saga, smart, sensuous, and careerist, while Hampton is brilliant, cynical, and predictably alcoholic. When Will and Summer embark on what appears a perfect relationship, Hampton shows up occasionally as the Not-Will, doubting motives, desires, and candidates, bedding younger and younger women, and lapsing into witty irrelevance (he notes Will’s affiliation with the Cheese State, sees through Clinton’s posturing).
As Emily is too provincial and Summer is too ambitious, April (Isla Fisher) is more generally too much. A Nirvana fan with a perpetually absent rocker boyfriend, she works making copies at the Clinton campaign office. Still, she’s not a believer for a minute, debating Will about Clinton’s merits just as the Gennifer Flowers story breaks on TV. “You’re right about one thing,” she chides Will. “He ‘gets’ women.” Erk. As the film persists in situating Will’s learning curve alongside the “era” his candidate embodies, its structure is simultaneously allusive and uncomfortable, especially when Maya breaks in asking for answers, eventually reduced to tears when she suddenly realizes that all the convolutions might lead to a wowza ending, namely, that Will is not her father. Her trembling lip and big wet eyes inspires him to reassure her absolutely before he finishes the story about her mom, but the moment is an odd one, suggesting not only the film’s investment in uncertainty (“mystery”) as narrative device, but also its most salient point about the ‘90s, that for all its reputation as a time of national hope and prosperity, it was also, always, a time of distrust, betrayal, and politics as usual.
This much is made manifest when Will takes on his last political job, for mayoral candidate Arthur Robredo (Nestor Serrano). (Will is introduced as an ad exec, working on campaigns for Quaker Oats and Cap’n Crunch.) Though Definitely, Maybe doesn’t specify Robredo’s politics, his general smarminess is clear enough, and so he must become an object lesson for Our Will, who makes wrong decisions and draws some strange moral lines, en route to discovering… Mrs. Right. As the film devolves into pap, you see that its use of the faux-familiar political backdrop is in the end incidental, just one way to get to the requisite ideal romance. It’s nice for Maya to be able to believe in her dad’s happy ending, even if the rest of us are left with disheartening political facts and fictions.