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Definitely, Maybe (2008) Poster

Goofs

Factual errors 

In the beginning of the movie, on a close-up of the divorce papers, the word "Judgement" is used. In the USA, it should be spelled "Judgment".
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Anachronisms 

The cell phone number that Emily gives Will at Summer's party has a 212 area code. At that time, the 212 area code was for NYC land lines only.
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In a scene just after the 15 minute mark, when Ryan Reynolds' character first arrives in New York in 1991, as he passes by the TGI Friday's on Eighth Avenue, a white Mercedes-Benz CLK convertible (W209 model) drives by, which could have been manufactured no earlier than 2003.
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When William first visits April in her apartment during the Bill Clinton 1992 New York primary campaign, April plays "In Spite Of Me" by Morphine (followed by Nirvana's "Come As You Are"). "In Spite Of Me" wasn't released until Morphine's September 1993 album Cure For Pain.
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When Will is talking to Hampton, the bookshelf behind Will has a hardcover copy of David McCullough's "Truman" on it, which wasn't published until June 1992.
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When Rachel Weisz tries to sober up Ryan Reynolds in 1991 (he's working on the first Bill Clinton campaign), she gives him a modern style bottled water - which was not available in 1991.
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Continuity 

During the scene where Maya convinces Will to tell about his past relationships, her braid switches from being on her shoulder to hanging down her back in between shots.
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When Will prepares to leave Madison, Wisconsin, after the New Year's celebration, there's green and full foliage on the trees. Highly unlikely in January 1992, global warming notwithstanding.
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When Will is asked to get people to attend the dinner for donations his boss says it's on Monday night, but on the phone Will says that its on Thursday night.
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Will throws a noodle onto the TV but when April some in there are two extra noodles hanging there.
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When Will goes to visit Summer, Hampton opens the door with his glasses hanging partly under his chin. He adjusts it correctly and then invites Will in. When they're inside the apartment, Hampton's glasses is crooked and under the chin again.
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When Will is in April's apartment before they kiss, her hair keeps switching from framing her face to being pushed back or behind her ear.
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When Summer is sitting by Hampton's bed in the hospital, when we look at her she is holding her head up with her right hand, but when we look at her from behind she is not.
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Will is sitting outside a small restaurant. Just before Summer's surprise reappearance, the waitress serves him his wine and asks him if he has made up his mind yet. At his place is a sandwich with fries etc, just barely started.
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When Will and April are smoking outside Two Guys, April's cigarette constantly switches from her right to her left hand depending on camera angle [facing her, left hand; facing Will, right hand]. Same thing with her hair in her apartment on the couch with her hair [framing the left side of her face, framing the right].
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When Will takes the book to April's apartment, her roommate locks the door after he enters. When Will leaves after his encounter with Kevin, he walks out the door without unlocking it.
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Crew or equipment visible 

As Emily turns to walk away at the zoo, the transmitter for her wireless microphone is visible under the back of her sweater.
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When Will starts calling people to reserve seats, the camera starts going around Will and for a few seconds, you can see a grip off to the far right (visible in wide-screen only).
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Errors in geography 

The ends scene by April's apartment in Brooklyn shows a steam construction site with a stack in the background. In New York there is only steam in Manhattan, not in the streets of Brooklyn.
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Factual errors 

When Will and Summer are called to the hospital, a nurse tells them that Hampton has suffered an "aortal rupture." In medical terminology, all terms relating to the aorta are "aortic". There is no such word as aortal. Notwithstanding this, an aortic rupture is a life threatening condition. Anyone who has this would either be dead or in the Intensive Care Unit heavily sedated, not conversing easily like Hampton was. At the very least, he should have had a blood transfusion bag hanging over his bed.
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Incorrectly regarded as goofs 

Everything we see of the events that happened in the early 1990s (his first contacts with Emily, April, and Summer) is Will's recollection of how things happened. Since Will is retelling the tales of events that happened many years previously, how the events played out and any anachronisms (e.g. what people were wearing) is subject to the fallibilities of human memory.
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During the scene where Will and April are smoking outside the store we see that Will's cigarette has a white filter. Will bought Morley Reds, which is a fictional brand used in movies. The pack has the appearance of Marlboro Reds, which have always had brown filters, leading some people to think his cigarette was a goof.
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Revealing mistakes 

When Will and April are comparing cigarettes, Will buys a pack of Marlboro Reds. When he is smoking outside in the rain, the cigarette is completely white. Marlboro Reds have brown paper around the filter area of the cigarette.
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See also

Trivia | Crazy Credits | Quotes | Alternate Versions | Connections | Soundtracks

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