This review originally appeared as a guest post on 10 Years Ago: Films in Retrospective, a film site in which editor Marcus Gorman and various contributors revisit a movie on the week of its tenth anniversary. This retro review will be a bit more free-form, recappy, and profanity-laden than usual.

Ad exec Will (Ryan Reynolds) wanders through Manhattan to pick up his daughter, playing “the perfect song” for when you’ve just been served with divorce papers: “Everyday People” by Sly & the Family Stone. Let’s agree to disagree, movie. This is perhaps the most generic song until “ABC” the following year, and it isn’t nearly as catchy. My overt hostility this early into the film should tell you what to expect here – this is the first 10YA film I’ve rewatched and found substantially less enjoyable than my first viewing a decade ago. So let’s do this thing. Will’s tiny individual Bluetooth earbuds indicate that he is abundantly wealthy and tech-savvy by 2008 standards (these are still barely a thing). He interacts with a series of New York street people from central casting as the credits play, then wanders up to his daughter’s school.

“Sometimes, no matter how carefully you plan your playlist, there is no right track for what awaits you.”

I normally begin my 10YA reviews with a selection from the opening voiceover, but this is really the first time it’s been this trite and inconsequential. His song is uninspired, his metaphor is now dated, and “what awaits him” is a bit of a cacophony at the school because the kids have just started sex-ed. His daughter Maya (Abigail Breslin) explains the mechanics of sex, and asks a perfectly reasonable question – her friend Sammy Boigon’s sister says he was an accident, and how do you accidentally thrust a penis into a vagina? Will shuts her down, telling her to stop saying such accurate words (“say tinkle-part or wee-wee or something cute”) – bad form, Will. Comprehensive sex-ed is better for a reason. She then asks more pointedly, “If they didn’t want to have a baby, why did they have sex?” Will misses a second teachable moment, and says they were rehearsing. He’ll miss another one later when his daughter asks, “What’s the boy word for slut?” One thing I’ve done since 2008 is become a parent, and I really try not to judge how other parents handle common pitfalls. But Will seriously biffs this moment, and given that it’s one of the only consequential moments with his daughter until the end of the film, it seems worth noting.

Anyway, all of this was an awkward lead-in to Maya asking how Will met her mother. Does this premise sound familiar? The CBS series “How I Met Your Mother” was in its third season and largely unknown to me in 2008, although seeing this film may have seeded my interest in it. Now that I’ve seen that whole series, which spawned a skip list and series-end podcast in which I called it “one of the finest sitcoms on television,” this film suffers by comparison, both in the credibility and structure of the story, and the likability of the characters. More on that later. Will agrees to tell Maya the complete story of his adult dating life, but he’s going to change the names, and he won’t reveal until the end who her mother is. Definitely, Maybe does a poor job of justifying its premise. It attempts to lend a sense of urgency and purpose to the story by couching it as Maya’s precocious attempt to “solve” her parents’ impending divorce. And Will makes it clear (to the audience) that he knows this, but never that he’s doing this for some definable purpose, or even against his better judgment. Beyond the appropriateness of the subject matter, this just really seems like a bad idea. But…what the hell do I know, I’ve never been divorced. To call this situation desperate and sad seems a bit obvious, but it’s all I’ve got going in.

The tale begins. In 1992, Will is a volunteer for the Young Democrats of America in Madison, Wisconsin, and we meet Lady #1: Will’s college sweetheart, Emily (Elizabeth Banks). If I remember correctly, this is Maya’s mother. I obviously didn’t know this the first time I saw the film, but seeing it now, the film definitely pats itself on the back several times for hiding this result. Maya even guesses that it’s never the first girlfriend you meet – which implies that she knows more stories in this “rom-com mystery” genre that I’m unaware of. The only other one I can think of is Extraterrestrial, and the mystery there was “What’s up with the alien spaceship hovering over our one-night stand?”, but no matter. These particular early-90s Democrats work for the Clintons, and Will is leaving for New York to work for Bill’s presidential campaign. Because Will wants to be president. I give the movie kudos for presenting Will’s political aspirations (with a mix of real and fictional politicians) as something admirable and sincere. Reynolds plays Will’s later disappointment with President Clinton’s scandals in a way that feels genuine and devoid of cynicism. Clinton is his idol, and his fall from grace disappoints him. It doesn’t count for much of the film’s plot, but it’s something.

Emily, who is staying behind, sends Will along with a book-sized package to return to one Summer Hartley (Rachel Weisz), whom she met on her exchange program at Cambridge. You may be assuming that this means Weisz will speak with her native British accent, and you would be wrong. Emily notes that all the guys wanted to sleep with her, and Will suggests that perhaps she should mail it instead. Whoops. We haven’t seen her yet, but Summer is Lady #2, and Will is definitely, 100% going to sleep with her. Flying into New York, Will looks out the window and sees…what looks like archive footage of the NYC skyline. The WTC towers are visible, but also it looks a bit grainy, which is a strange thing to see in HD. He’s handed a cellular telephone just slightly more advanced than the one Zack Morris carried in ’92, and is sent to get coffee and bagels. When he returns, he wipes out offscreen into the men’s room with a comically huge pile of TP while the campaign manager briefs everyone, and screams “what am I doing here?!” We get it, movie. Shit rolls downhill. This film largely predates the gig economy, but Will’s bitching about his no-future entry-level political job feels petty. Suck it up, intern.

Will meets April (Isla Fisher) at the copy machine, and they flirt. April is apolitical – this is just a gig for her. She’s also Lady #3. Will makes some vague promises about how great Clinton will be for African-Americans and women, and then the Gennifer Flowers scandal breaks. Whoops. The campaign gang goes out for beers, and they spontaneously compare notes on who their romantic “types” are. Will’s type is brunettes with horn-rimmed glasses (neither Emily nor April). He drunk-dials Emily, who correctly concludes that he’s never coming back from NYC. Back in his room, with some prodding from his campaign roommate Russell (Derek Luke), Will rips open the package from Emily and finds…a diary. They decide they can’t read it. Then they read it, it plays as light erotica written by a dude, and it seems that Summer might be Emily’s ex-lover. I’ll go ahead and admit an area of personal growth for me here: This is definitely something that would’ve seemed like a bigger deal to me in 2008 than now – I didn’t really grok the Kinsey scale in those days, and this sort of revelation would’ve made me feel insecure in a more categorical way than the existence of ex-boyfriends. But it’s a personal hang-up that I find silly in retrospect (you’re either confident the person you’re dating likes you, or you’re not), and I’m glad to be past it.

Will heads over to Summer’s apartment without calling first, and finds Kevin Kline in an open bathrobe. He is Professor Hampton Roth. Will asks if he is Summer’s father, and he confirms, “Yeah, I’m her daddy.” Gross. Then – and I’ll pause here to note that it’s about 10AM – he pours some Johnny Walker. The boys get hammered and pass out, and Will awakens to the face of Summer, who introduces the professor as her boyfriend (and thesis advisor). They engage in some flirtatious banter in Weisz’s hit-or-miss American accent. This was a miss. The accent, and the character. She asks if he read the erotica-diary, throws it at him and suggests that he read it when he’s lonely, then follows him into the hallway and kisses him. “Sorry,” Summer says, “I was just curious. Hampton encourages me to cultivate my curiosity.” Ugh. These two met 60 seconds ago. This is utterly bizarre, even in this genre.

Back at the campaign, Will is stapling signs, nearly staples his hand, and screams aloud again, “What am I doing here?!” Each of these complaint beats feels like the failure mode of an “As Seen on TV” commercial. Luckily, the movie has also lost patience with this, and campaign manager Arthur Robredo (Nestor Serrano) realizes he needs someone with a Wisconsin connection to court Madison donors in the NY area. Will now has a desk and a real job, and it turns out he’s an ace at it, selling out an entire fundraiser table. He runs into April buying cigarettes at the convenience store, and the two have a dumb argument about which of their brands is healthier and/or burns faster. Then they proceed to have a competitive smoke-off. During the ensuing chat, we learn that it’s April’s birthday, her musician boyfriend stood her up (on her birthday!). She wins the bet, but declines the payoff, and they haggle their way into attending a party together. They end up on a rooftop, and Will reveals that he plans to propose to Emily when she comes to NYC. April invites Will to practice the proposal on her. He starts with a half-assed “Will you, um, marry me?”, and she gives a solid rehearsed speech excoriating him for it. This is a decent scene – not because of the overwritten rom-com speeches, but because April is not being a ridiculous caricature here – perhaps just a bit heightened. She’s neither manic, nor pixie. I buy that she has a life outside of this moment. They go back to her apartment for tea, and they have a nice chat about a copy of Jane Eyre that her father inscribed and gave her before his untimely death. This’ll be important later. They chat all night about music, politics, travel, etc, and she tosses in a line about how this is nice that they can just sit here and chat and not have to worry about flirting or all the attraction stuff. Then they frantically make out, and then he leaves. It’s a mess. So far, I believe this relationship the most of the three.

Back in the hotel, Emily – Will’s actual girlfriend, remember – has arrived on the red-eye to surprise him in the morning! She takes the elevator, he takes the stairs, and he magically gets to the room…long after she does. Well played, movie. But it’s fine, because his roommate has covered for him. They kiss, and Emily notes a bit frantically that his tongue tastes different. They wander through Central Park, and Will tells a rambling story of how his father ran into an ex on his way to propose to his mother (meta-story!), and it turns out he’s proposing to Emily now, and Emily panics and scream-admits that she slept with Will’s roommate Charlie. So it’s over. And I now remember with absolute certainty that Emily is the mother, so at some point this will all be a double-reversal. Back at the campaign, Bill Clinton has won the New York primary (and three others, including Wisconsin), and it’s party time. April drops by to see why Will is so miserable, and they banter and apologize for the kissing. They have a competitive metaphor-off for how disastrous their hypothetical romance would be, and she wins with “Sandpaper and bare ass (you’d be the ass)”. Then she asks him to dance. I continue to buy this relationship the most of the three.

Will and Russell hit the road to continue with the campaign. And then time advances, montage-style. Once Clinton is elected, the two form their own political consultancy, and they join the [fictitious] gubernatorial campaign of their old boss, Arthur Robredo. Will starts dating again, April dumps her loser boyfriend and goes traveling, and the two become pen pals, and fast friends. It’s 1994 in New York. Will lazily informs us that the internet is getting started, everyone on the street has a large (but not huge) cell phone, and I start to think this movie has Forrest Gump ambitions of being a time capsule for future rosy-eyed nostalgia. It would really need a better soundtrack for that. Will gets invited to a book signing with Professor Roth, and runs into Summer again. Summer is writing for NYMag, and the professor has moved on to dating a pair of college freshmen. Legal, but still gross. And the three of them engage in more preposterous banter. It is utter nonsense that any of these people would remember each other from a single meeting two years earlier (kisses and drunkenness notwithstanding), and all of this feels forced. Summer agrees to write an article about the campaign. She and Will go out for dinner again, flirt like crazy some more, and montage their way into a relationship (much of which is weirdly musically-focused and takes place on the same park bench). They make out on various couches, decide to spend the whole day in bed together, then they’re immediately called away to the hospital to tend to Professor Roth, who has had an aortic rupture (a condition with a 90% mortality rate) and is somehow still alive. Roth is just conscious enough to criticize her for not writing a sufficiently hard-hitting exposé on Robredo’s campaign, seeding the destruction of this relationship, which is barely five minutes old in movie time.

And then April returns. They wander the streets, and she tells a story of bursting into tears after making out with a hot stranger on a Cretan beach, because she realized that she couldn’t see a relationship with this guy going well. And then she realized she simply had to tell someone specific about this, and that someone is right in front of her face- annnnd while they’ve been talking, they’ve walked into a jewelry store because Will is picking up a diamond engagement ring for Summer. Whoops! Back in the present day, daughter Maya recites some subtext: “Weren’t you listening? She came home for you!” Will looks pensive, as if he somehow didn’t realize this. This is where the structure of the movie strains credulity a bit. It’s certainly possible for someone to interrupt a personal anecdote to say, “Hey, you were the asshole there”. But it doesn’t really make sense that Will would tell this story, which obviously emphasizes April as a major participant, if he never realized that April was one of his own love interests. He can tell the story of how he met Maya’s mother, but April is only an important character if she’s a potential mother, and it sounds like Will is supposed to be gobsmacked by this sudden realization.

Back in ’94, he goes to meet Summer. NYMag has asked her to do a followup on Robredo, which she has already written, and it’s a doozy: Robredo abused his political influence to get a friend an early parole from prison. Will says this is bad…that his boss is the “tough-on-crime Democrat”. Then he tells her if she hands this in, “we won’t survive this.” Summer starts to equivocate, and then he makes it clearer. “I’m talking about you and me.” This is the point in the story in which I interrupt Will and say, “Hey, you were the asshole there,” because that’s a hell of a thing to say to someone you’re about to propose to. It’s also the point where I say the same thing to Summer, because writing an exposé about her boyfriend’s campaign…well, I’m no journalist, but it sounds like a serious conflict of interest. And it turns out she’s already handed it in, so the campaign and the relationship are over. The relationship careening off a cliff makes sense, since this relationship was utter tosh to begin with – but politically, this feels quaint in a post-2016 world. This is a mundane bit of patronage, and it’s hard to imagine this scandal would torpedo a campaign today, when every politician with a national profile is gleefully ignoring multiple career-defining scandals each week. The world got weird and ugly. The GOP backed Roy Moore. And this would barely make a dent today.

Speaking of scandal, we flash forward to 1997, when Clinton is about to be impeached, and April finally calls Will back, leading with “Are you watching?” I guess their meta-awareness that they’re in a story is just something I’ll have to suspend disbelief on, because this is a weird way to call someone after a three-year break. They banter. April is quite sure that Bill did it, saying of Monica Lewinsky, “Look at the picture of her! I love her, she’s so his type.” I was rather incredulous at this line – both because we seem to have found the one person in 1997 who was kind to Lewinsky, and because… Well. I’m not going to pretend we (or I) have found some sudden piety on the subject of powerful men abusing their positions to make advances on the women in their employment in the past six months, much less the past decade since I first saw the film. This is an issue we’ll be coming to terms with for a long time as we begin the slow, generational task of reducing the incidence of women being drummed out of male-dominated industries by sexual harassment from men in supervisory roles. That said, it seems worth acknowledging that “she is so his type,” while perhaps a period-accurate statement for someone to make in 1997, is a little fucked up. As if type has much bearing on it when he’s the President of the United States.

Later, Will and April are back in a diner, and they discuss the nature of finding “the One”. April says it’s not a matter of who, but when – you reach a point where you’re ready to settle down, and whoever you’re with then becomes The One. More on this at the end. But first, Will dopily inquires if there’s ever been a guy that made her think, “This is it, this is him.” Isla Fisher kills this moment, because standard rom-com misfortune dictates that she has had this exact thought about Will, but April reveals just enough of this for the audience, but not enough for dunderhead Will. Then she reveals that she’s seeing someone (a dude named Kevin), and Will gets drunk. He’s disappointed with his life, Clinton’s linguistic dickery over the word ‘is’, and obviously the April situation. He checks his answering machine (kids, this was like a Google Home that only worked offline), and finds messages from April about his upcoming birthday, a surprise call from Emily (who is in New York), and April again. He wraps himself in a blue blanket of sadness, and April shows up at his door. This is the second time she has come looking for him when he’s being a sad sack and avoiding a party. This happened to me once in my early 20s, and I also failed to pick up on its meaning at the time. Will fails similarly, falling on his face off-screen as April marvels inconsequentially as his disheveled apartment, and- WHOA. Aggressive smash cut to them arriving at the party, and it really feels like there was supposed to be more dialogue here. I guess the movie was running long.

Here we see most of the minor characters from earlier in the movie. They chat about Bill Clinton, whom Will has genuinely lost faith in, and thinks maybe should be impeached. Will leaves the party, gets drunk (again), and wanders to April’s doorstep, where she finds him and cheekily berates him for missing his cake, which she baked (*sigh*). And hang on, folks, because this scene is quite a ride. He quotes Nirvana. She takes an intimate swig of his beer without asking. He calls her beautiful and she thanks him. He drunkenly confesses that he likes her, then soberly confesses that he’s in love with her. He then projects some insecurity onto her, and she says he’s an idiot. He kisses her, and she pulls away and demands to know why he didn’t tell her sooner, instead of like this, when his “shit is a mess”. And he apparently took the ‘mess’ thing personally because he gets personal, and nasty. Nastier than their friendship can withstand. He insults her life and her career and her choices, and then twists the knife by saying he’s just saying this as a friend. She slaps him and goes inside. Reynolds made his bones playing the loveable asshole, but I’ve seen him play truly unlikeable only a handful of times. It works for the villain at a nostalgic theme park, but not the hero of a romantic drama.

Will wanders past a bookstore and finds the lost copy of Jane Eyre that both he and April were looking for, with the inscription from her father inside. Finding a specific lost copy of a book is a ridiculous plot device, but we’re moving at lightning speed now, and this is the only artifact that can save this relationship. He arrives at April’s apartment to deliver it. April’s roommate answers the door, and she is visibly amused by the torrent of sad sack apology messages he has apparently been leaving on the answering machine, because restraining orders don’t exist in Comedy World. She lets him into their gargantuan apartment, where he finds April’s boyfriend Kevin, who is Model-Hot, and who mentions he lives with her. This means Kevin should also be aware of the apology messages, so he’s either the most chill dude in the world, or he just sees Will as that non-threatening. Will leaves. Oh, and April’s in grad school now, so his abusive rant apparently stoked her ambition. More on this later.

Next up, he’s at a sidewalk café, a waitress brings him a gigantic glass of wine, and asks, “Do you know what you want yet?” “No, ” he responds, with a dumb double meaning. Summer wanders up, and is pregnant. Baby-daddy’s out of the picture, and she invites him to a party to make amends, and – whoa whoa whoa. Back in the present, Maya is now completely freaked out and demands to know if Will is really her father, and I have to say, the movie is being downright sadistic now. He is her father, and he’s a terrible one at that. He says this story has a happy ending, and she demands to know how that could possibly be, when whoever her mother is, they’re getting divorced. He offers to stop, then goes to get her a cup of tea before they continue. She falls asleep. Poor kid. The next morning, they get a bagel and continue the story. Will arrives at Summer’s party, and gives her flowers. She makes niceties, we learn that Professor Roth died alone in his office, and he…accuses her of planning to seduce him. Seriously, this rom-com narcissism is getting tedious. It’s like Will has read the script and knows these women are required to be into him (à la Black Mirror‘s “USS Callister”). She shrugs that off and asks if they can be friends, he agrees, and she leads him across the room to meet an old friend…his ex-girlfriend Emily, who lives in New York now. The two share some easy banter over whether he intended to call her, and he puts her number directly into his Motorola StarTac (I had one of those!) because he actually means to call her back this time. Later, Emily and Will wander in the park, and she makes overtures about continuing the relationship, and reaches up and strokes the side of his head, and BAM – Maya figured it out. Emily (real name: Sarah) is her mother, because she does that head-stroking thing to her too. Do I even need to point out that it would seem a bit odd for Will to include this particular visual detail in a story told verbally? No? Okay, let’s move on.

Sarah (who is Emily, remember) walks up, and they all share a stoic trip to the zoo. They stand in front of the penguins, and Maya teaches them all about lifelong penguin monogamy. It’s sad. We don’t know why these two are splitting up any more than we know why they got back together, so it’s hard to invest much in this scene apart from the grim knowledge that there must be a good reason. Maya leaves with her mother, then runs back to thank her dad for telling her the story. Will says he forgot to tell her the happy ending. He looks his daughter in the eye: “You.” They embrace. It’s a sweet and completely unearned moment. Bless her, Abigail Breslin adds almost nothing to this film. This girl was Little Miss Sunshine, and here she is relegated to a sympathetic sounding board for a midlife crisis. Then Bill Clinton (impersonator Dale Leigh) jogs by with a Secret Service detail, and Will shouts a greeting. Clinton waves, and…Will has closure, I guess? About something?

Will goes back to his office, signs the divorce papers, and finds the copy of Jane Eyre that he located for April, now many years earlier. And it’s happy ending time. He finds April at the offices of Amnesty International, in an unspecified do-gooder dream job. And here’s something I definitely didn’t realize in 2008: the movie is pretty clearly telling us that the torrent of drunken abuse that Will threw at April earlier was instrumental in helping her go back to school and get her life back on track, and this feels deeply unsettling in retrospect. All that we saw of April earlier was that she was confident, capable, gainfully employed, had saved enough money to go traveling (and then did so), and was in multiple relationships that we have no particular reason to believe were unhealthy. Will’s criticism of her in that scene is all the more baffling because it comes out of nowhere, and if the movie intended for him to be wrong or misguided, it does a terrible job of showing it. April laughs at him on arrival (in a “happy to see you” sorta way). They trade details: No one’s dating anyone, no one’s currently smoking, he just got divorced (which she somehow heard already), and the two are maybe finally ready to be together? He gives her the book. She cries and thanks him. He completely unnecessarily tells her that he’s had it for years, and apologizes. She tells him to leave. Come on, movie. Coffee is for closers.

Back home, Maya berates him, and reveals that Summer’s real name is Natasha (“who writes for that magazine”), and asks why he didn’t change April’s name in the story. She tells him he’s not happy. He tells her to get her coat. They head for Brooklyn. This is incredibly inappropriate, and I guess it’s really happening… They buzz April’s apartment, she demands to know who the kid is speaking in the background. He tells her. “That’s kinda cheating, isn’t it? Bringing your daughter?” Yes, April, yes it is. They decide to count to thirty and leave if April doesn’t come down. As April listens to this on the intercom, Maya tells Will he should tell April the story, and “Then she’ll know!”. They reach 30 and start to walk away, and April bounds out the front door, surprising no one, to ask, “What story?” He says he kept the book because it was the only thing he had left of her, and he couldn’t let her go completely. They embrace. Then they go inside for some awkward storytime, but not before the two grownups pop back out to the front step for a huge smooch. Annnnd we’re out. Good luck folks.

At the risk of vaguely spoiling How I Met Your Mother, the series did all of the same things as this movie, and it certainly had its share of redundancy and meandering subplots. It tried to have its ending both ways in a similar manner, giving the main character a happy (but ultimately doomed) romance with one character, only to pair him with another at the end. But what was it all for? Well, in How I Met Your Mother, the explicit message (as narrated by Bob Saget) was that love is hard, but it’s worth it, because it’s the best thing we do. The only thing close to a coherent message I can extract from Definitely, Maybe is April’s speech about finding The One – that at a certain point, everyone just decides they’re ready, at which point they love The One they’re with. It’s a glib message, but it’s one that’s supported by the complete lack of foundation for Will’s romance –
and re-romance – with Emily/Sarah. All we ever saw of this relationship was failure. I don’t know why these two were ever together, apart from the convenience of college geography, and I have no idea why they got back together, apart from quarter-life desperation. But at least they got a nice kid out of it?

FilmWonk rating: 4 out of 10