[[quoteright:259:https://static.tvtropes.org/pmwiki/pub/images/definitelymaybe.jpg]]

A 2008 RomanticComedy written and directed by Adam Brooks. It stars Creator/RyanReynolds, Creator/ElizabethBanks, Creator/IslaFisher, Creator/RachelWeisz, and Creator/KevinKline.

Reynolds plays Will Hayes, a divorced 38 year old father. His 10 year old daughter Maya (Creator/AbigailBreslin), lives with her mother but visits him twice a week. On one of these visits, after her first sex education class at school, Maya asks him to recount the story of how he and her mother met, and though initially reluctant to do so, he eventually relents and agrees to tell her the story, on the condition that he be allowed to change the names and some of the facts.

It all begins in 1992 when Will, having just graduated college as an idealistic young aspiring politician, moves from Wisconsin to New York City to work for UsefulNotes/BillClinton's presidential campaign along with his best friend Russell (Derek Luke). The initial plan is for Emily (Banks), his college girlfriend, to join him after a few months, at which time he intends to propose, but things don't go according to plan and Will ends up going through multiple relationships and years of romantic highs and lows before settling down with the woman he eventually marries. In addition to Emily, the women who come into his life are April (Fisher), a co-worker from the campaign, and Summer (Weisz), Emily's former roommate and a magazine writer who is in a relationship with her much older thesis tutor (Kline) when Will meets her; it is left to Maya (and the audience) to try to determine which of the three Will ended up with, and thus which of the three is Maya's mother.

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!! This film contains examples of the following tropes:

* ActorAllusion:
** There is a shot of "Two Guys" pizza. Ryan Reynolds was in ''Series/TwoGuysAGirlAndAPizzaPlace''.
** Hampton, played by Kevin Kline, telling Hayes to be masculine might get the audience a throwback to the wonderful "How to be a man" scene from ''Film/InAndOut''.
* AffectionateGestureToTheHead: Recognizing the gesture is how Maya works out which of the women in the story is her mother.
* AmicablyDivorced: Will and Maya's mother ([[spoiler:Sarah/Emily]]) are on good terms.
* AndStarring: Creator/RachelWeisz in the OBB.
* AnimalMetaphor: The daughter tells her divorced parents that penguins mate for life, but sometimes the husband and wife penguins get separated 'cause of their migratory patterns and sometimes they're apart for years, but they almost always find each other.
* BelligerentSexualTension: Will and April have this dynamic at first, as they snark at each other quite a bit from the first time they meet, although since they don't get together it remains {{UST}}.
* BigApplesauce: Though Will is from Wisconsin, almost the entire movie takes place in New York.
* BlackBestFriend: Russell and Will have been friends for a long time.
* BlondeBrunetteRedhead: There's one of each among the primary love interests - blonde (Emily), brunette (Summer), and redhead (April).
* BoyMeetsGirl: Averted. More realistically, it's boy meets one girl, then another, and then another, and tries (unsuccessfully) to find lasting love with each of them in turn.
* BreakHisHeartToSaveHim: [[spoiler:Emily thinks Will would be better off not tying himself down at a young age, and refuses his marriage proposal. When he insists, she informs him that she cheated on him, and it's suggested she did so to make breaking up with him easier.]]
* BusinessTripAdultery: While working on the Clinton campaign in New York, Will's girlfriend cheats on him with his roommate.
* CassandraTruth: [[spoiler:Charlie jokingly warns Will that he shouldn't leave "Emily" alone with him. Then again, it is later implied that Emily just used him as a scapegoat for the BreakHisHeartToSaveHim above to become easier.]]
* CheerfulChild: Maya is ''very'' cheerful and understanding for a 10 year old, despite the fact that her father tells her some rather sordid and unhappy details about his past life.
* ChekhovsGun:
** [[spoiler:Emily/Sarah]]'s AffectionateGestureToTheHead.
** [[spoiler:Emily/Sarah]]'s voice message stating that [[spoiler: she now lives in New York]].
** April's ''Literature/JaneEyre'' book signed by her late father. [[spoiler:It becomes the last piece to make Will and April's relationship fruitful at the end]].
* ChickMagnet: Both Will and Hampton.
* CodeName: Will calls his exes by alternate names, presumably to conceal their identity from his daughter who knows her mother's real name. [[spoiler:She realizes her dad's in love with April because he doesn't give her a code name.]]
* ComicRolePlay: Will practices his proposal speech with April standing in for Emily. The speech:
-->'''Will:''' "Will you, um, marry me?"
* TheCynic: April is quite jaded. Since Will is a WideEyedIdealist, this makes them a CynicIdealistDuo.
* DeadpanSnarker: April is quite biting and sarcastic, even when she's [[BelligerentSexualTension flirting with Will]].
* DisposableFiance: Subverted. [[spoiler: Will and Sarah/Emily do end up getting married in the end]]. Although the fact that [[spoiler: they are now divorced and its implied that Will may end up with April]] may make this a DoubleSubversion.
* DivorceIsTemporary: [[spoiler:Thankfully averted. Maya eventually accepts that her parents aren't the {{OTP}}.]]
* DrowningMySorrows: Will starts to drink heavily after finding out that April is dating a new guy at one point.
* EarnYourHappyEnding: [[spoiler:After Will has been divorced by Sarah (Emily), it's suggested at the end that he may get together with April, after much heartache and years of not even speaking to each other.]]
* EurekaMoment: Maya, when she figures out that [[spoiler:Emily (aka Sarah) is her mother]].
* ExperimentedInCollege: While Summer is an admitted, dyed-in-the-wool bisexual, this was [[spoiler: Emily's]] take on their time together.
* FallingInLoveMontage: Will and Summer, to the tune of the latter's version of "I've Gotta Crush on You".
* FieryRedhead: Downplayed with April. While she doesn't have a HairTriggerTemper, she is the snarkiest and most temperamental of the three women.
* FirstGirlWins: Maya's mother ends up being [[spoiler:Emily, with whom Will once again gets together after years apart.]] Subverted in that the two are now divorced.
* {{Foreshadowing}}: Take a look at Maya's tally sheet. Pay ''very close'' attention to the color she uses...
* FramingDevice: Most of the events the movie depicts are framed as the story Will is telling his daughter in the present day.
* GenreSavvy: Maya knows that April's like the character in the story who's always been the friend. Then she realized she doesn't just want to be the friend. She wants to be the girlfriend, except it's too late. Maya had to explain to Will that April had come home for him.
* GirlOnGirlIsHot: At one point Will and Russell discuss this after coming across a description of a lesbian kiss in Summer's diary.
* GracefulLadiesLikePurple: April constantly seems to favor this.
* GreyAndGreyMorality: Unlike in most romantic comedies, none of the characters is entirely saintly or entirely psychotic in their relationships - they're all flawed but well-meaning people trying to figure out what's best for themselves.
* HappilyEverAfter: Subverted. One of the first things the audience learns is that Will is being divorced by the woman he married.
* HowWeGotHere: The framing device of the movie.
* IAlwaysWantedToSayThat: When Hampton ends up in the emergency room and the nurse asks if he's comfortable, he responds, "I make a living." When the nurse, Summer and Will look at him, Hampton responds he deserves at least a smile because he's been waiting his whole life to make that joke.
* InMediasRes: Sort of. The movie is a [[SubvertedTrope subversion]] of the typical romantic comedy plotline in that there is no neat resolution to Will's pursuit of love at the end.
* InstantlyProvenWrong: As Will tries to argue to April that Gov. Clinton is great to women, the Gennifer Flowers scandal unfolds on the television behind him.
* IntrepidReporter: Summer. [[spoiler:It's why she and Will break up. She targets the political candidate he is working for.]]
* IronicEcho: "We've all gotta make copies sometime; your time is now" "Oh, very funny. You're really funny! What a dick."
* ItWillNeverCatchOn: During the '92 election, Will and his fellow campaigners watch a TV interview with the president's adviser and son George W. Bush, and are not impressed. Russell says, "If this guy's smart, he'll go back to baseball."
* KavorkaMan: Summer's journalism professor, Hampton Roth, who despite being nearly sixty is quite popular with female graduate students.
* KickTheDog: Despite Will begging her not to, [[spoiler:Summer goes ahead with the news story about his boss. She seems to show no regret for him losing his job and reputation from the scandal, even though he broke up with her. Later, Summer is pregnant and hints she wants to reconcile with Will, despite everything. When he refuses to bite, she decides to introduce him to one of her exes, realizing she went too far]].
* LastGirlWins: [[spoiler:Subverted. In fact, his relationship with Summer ended in a very bad way, though they later reconciled.]]
* LastMinuteHookUp: It's implied that [[spoiler:Will may get together with April in the present]].
* LittleBlackDress: Emily is wearing one during the climactic scene. Oddly, Summer never wore any of these.
* LongDistanceRelationship: Will and Emily, initially.
* LookingForLoveInAllTheWrongPlaces: April. Also Will to an extent.
* LoveDodecahedron: Will begins the story by noting that his romantic history is "complicated"; at one point Maya interrupts him to sum up the characters' various conflicting feelings for and relations to each other and admits he's right.
* LoveHurts: Will ends up going through multiple painful breakups.
* ManicPixieDreamGirl: April is set up as this, and Will seems to view her as such at first, though it's ultimately subverted as she turns out to be a person with a three dimensional personality and needs of her own. Summer also has elements of the character type.
* MaybeEverAfter: [[spoiler:At the end of the movie, Will finally gets together with April. Or maybe not. It's definitely implied that they reconcile as friends, and she leaps into his arms and kisses him which suggests they could get together romantically, but beyond that, it's left ambiguous.]]
* MeetCute: Will meets April (his coworker on the Clinton campaign) this way. [[spoiler: Subverted since they don't ever definitively get together romantically.]]
* MementoMacGuffin: April is searching for a copy of ''Literature/JaneEyre'' that was given to her by her late father shortly before he died, which plays a rather important role in the plot. In an interesting parallel, the book serves as the only remaining link from April to her father, and later on Will admits that it also serves as the only remaining link from him to her.
* NarrativeProfanityFilter: As a CallBack to the explanation that casual sex is "rehearsing" for making babies, it's implied that Will's been using that word a fair bit in his relation of the story;
-->'''Maya:''' I can't believe [[spoiler:Emily rehearsed with Charlie!]]
* TheNineties: Much of the story takes place in this era.
* NoBisexuals: Averted. Summer openly identifies as bisexual, which while less unusual by 2008 when the movie was made would've been somewhat rarer in the [[TheNineties 1990s]] when most of the story takes place.
* NoManOfWomanBorn: At her baby shower, Summer tells Will she wants him to meet one of her exes as she thinks they will get along. [[spoiler: Summer being bisexual, the ex turns out to be Emily. Will does [[ExactWords get along with her, marrying her and fathering Maya.]]]]
* OfficialCouple: Soundly averted. None of the three women is depicted as perfect for Will or the one he's meant to be with.
* OnceDoneNeverForgotten: Downplayed. Early in the movie Will embarrasses himself by dropping an armful of toilet paper rolls in front of a room full of his coworkers. They do make fun of him about it for a while by making toilet paper-related jokes at his expense, but eventually it's forgotten.
* OohMeAccentsSlipping: Two:
** Rachel Weisz, a little, particularly in the "I've Got A Crush On You" scene.
** Isla Fisher's accent comes and goes in each scene.
* ParentalSexualitySquick: During the opening scene where Will picks up his daughter just after they had sex ed, one girl can be heard screaming at her mother that the deed happened and that the girl now hates her mother.
* PluckyComicRelief: Maya plays this role with her naive questions and comments about Will's story.
* PopCulturalOsmosisFailure: April tells Will she's going with this musician who seems more interested in being the next Music/KurtCobain than he is in her. Will's response is, "Who's Kurt Cobain?"
* RealNameAsAnAlias: An important plot point, as [[spoiler: Will doesn't use an alias in describing April, which Maya takes as a clue that he has feelings for her]].
* ResurrectedRomance: [[spoiler: Ultimately subverted. Will and Emily/Sarah did get back together and married, but they are now divorced.]]
* TheReveal: Eventually, the viewer finds out which of the three women Will married ([[spoiler: it's Emily/Sarah]]).
* RomanticComedy: Though it subverts or deconstructs most of the typical tropes.
* RomanticFalseLead: There are several characters who would fit this role in a conventional romantic comedy, but it's consistently subverted as there is no OfficialCouple and they are generally (and realistically) just portrayed as other fish in the dating pool, not as obstacles to true love.
* SleazyPolitician: Will's first major client, Arthur Robredo, a candidate to be governor of New York. Will also ends up feeling this way about UsefulNotes/BillClinton.
* SlowClap: When Will manages to fill a whole table at the fundraiser: initiated by the Governor, no less. This is where his career starts to take off.
* SurprisinglyRealisticOutcome:
** [[spoiler:Emily revealed she cheated on Will and wasn't ready to marry him. It seems they can get over that rough patch a few years later when they reconcile and have matured. Not so much in the present; she and Will divorce on realizing they were incompatible]].
** Summer [[spoiler:wrecked Will's career with her article, without caring for the consequences when he was about to propose to her. She later appears pregnant with another man's child, leading to Maya to worry that Will might have gotten back together with her and he's not her actual father. We find out that Summer had the sense to realize she went too far and instead wants to set up Will with one of her exes]].
* TakeThat: The movie takes shots at both Democratic (Bill Clinton) and Republican (George W. Bush) politicians.
* TeacherStudentRomance: Hampton seems to enjoy dating his female graduate students.
* TitleDrop: April pretends to be Emily to help Will rehearse his proposal speech at one point - it's her reply when he asks her to marry him.
* TrueBlueFemininity: Emily's outfits are usually blue.
* TwentyMinutesIntoThePast: The movie was made in 2008. The story begins in 1992 and ends around the then-present, but mostly spans the mid to late [[TheNineties nineties]]. This is [[LampshadeHanging lampshaded]] by details such as Will's first boss handing him a brick-style cellphone on his first day on the job and Will asking "what's this?" in response and the campaign staff Will runs having to rely on dial-up internet at one point.
* TyingUpRomanticLooseEnds: Either subverted or averted entirely, depending on the character.
* UnrequitedLoveSwitcheroo: Happens between [[spoiler: Will and April]], as while they do develop feelings for each other at different times the timing never works. [[spoiler: Until the ending, [[MaybeEverAfter maybe.]]]]
* {{UST}}: Mostly between Will and April, the only one of the three with whom Will doesn't have a romantic relationship at some point.
* WhamShot: [[spoiler: When Will returned April's book, the camera zooms in on the dedication from her father and we see that her name is indeed April.]]
* WideEyedIdealist:
** Will is at first, about both love and politics.
** Maya's heavy-handed narrative about penguins mating for life, and what she hopes it will mean for her divorced parents, falls here too. Maya being a naive preteen, she fits this pretty generally.
* YouGetMeCoffee: Will's initial job at the campaign office in New York, literally.
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