History Film / DefinitelyMaybe

* 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, [[AmbiguousEnding maybe.]]]]

* 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 the [[TheNineties 1990s]] when most of the story takes place.

* IAlwaysWantedToSayThat: When Hampton ends up in the emergency room, and the nurse lectures him on his drinking and smoking, Hampton 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.

* 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 the [[TheNineties 1990s]] when most of the movie takes place.

* LastMinuteHookUp: It's implied that [[spoiler:Will gets back with April in the present]].

* 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, but beyond that, it's left ambiguous. Although the fact that it ends with her leaping into his arms and kissing him implies they do get together.]]

* FallingInLoveMontage: Will and Summer in tune of the latter's "I've Gotta Crush on You".

* TwentyMinutesIntoThePast: The movie was made in 2008. The story begins in 1992 and ends shortly before that time, but most spans the mid to late [[TheNineties 1990s]]. 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.

* 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, [[AmbiguousEnding maybe.]]

** April's ''Literature/JaneEyre'' book signed by her late father. [[spoiler:It becomes the last piece to make Hayes and April's relationship fruitful at the end]].

* NoBisexuals: Averted. Summer openly identifies as bisexual, which while less unusual by 2008 when the movie was made would've been somewhat more unsual in the the [[TheNineties 1990s]] when most of the movie takes place.

* TwentyMinutesIntoThePast: The movie was made in 2008. The story begins in 1992 and ends shortly before that time. This is [[LampshadeHanging lampshaded]] by 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.

* NeverLiveItDown: 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 for a while by making toilet paper-related jokes at his expense, but eventually it's forgotten.

* 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.

* TwentyMinutesIntoThePast: The movie was made in 2008. The story begins in 1992 and ends shortly before that time.

* YouGetMeCoffee: Will's job at the campaign office in New York.

%%* FirstFatherWins

%%* FramingDevice

%%* LoveHurts: At times.

%%* MeetCute: Will with April.

%%* OfficialCouple: Soundly averted.

%%* PluckyComicRelief: Maya.

%%* RealNameAsAnAlias: An important plot point.

%%* TheReveal: Eventually, the viewer finds out which of the three women Will married.

%%* TeacherStudentRomance: Hampton seems to favor this.

%%* TrueBlueFemininity: Emily's outfits are usually blue.
%%* TwentyMinutesIntoThePast

%%* DisposableFiance: Subverted.