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How Do You Know (2010) Poster

Trivia

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To date (March 2021), this is the last film to star Jack Nicholson, as well as the last film directed by James L. Brooks.
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One of the lesser known "big box-office bombs of all time"; the budget spiraled up to $120 million due to high salary demands of its principal cast and director (around $50 million), a lengthy production, as well as a costly re-shoot for the beginning and the ending. Coupled with marketing costs, the movie lost an estimated $105 million.
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Kathryn Hahn spent three days filming the scene where her character gives birth. In the early morning, after completing the shoot, she herself went into labor with her daughter Mae being born later that night. Two months later, Hahn would go back and complete filming the scene.
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To convincingly play a professional softball athlete, Reese Witherspoon practiced the sport for two to three hours every day for months. Ultimately, however, there's only about 20 seconds of her playing onscreen.
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A huge flop, this only made $7.6 million on its opening weekend.
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Kathryn Hahn - who plays a pregnant character in the film - was pregnant in real life when she got the part.
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The part of Lisa was written specifically for Reese Witherspoon.
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At one time, Bill Murray was in talks to play the role of Charles, but turned it down.
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James L. Brooks worked on the film for over 5 years.
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Jack Nicholson's and James L. Brooks' fourth film together.
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Former major league pitcher Jim Bouton, who wrote disparagingly of several bullpen coaches in his best-selling memoir "Ball Four" (1970), has a brief cameo as a bullpen coach.
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Paul Rudd and Reese Witherspoon appeared in Overnight Delivery (1998).
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Reese Witherspoon's character has a romantic relationship with Owen Wilson. Previously, Witherspoon played a character in Legally Blonde (2001), who had a romantic relationship with Luke Wilson (Owen's brother).
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Reese Witherspoon and Paul Rudd were voice actress and actor in Monsters vs. Aliens (2009), and their characters were love interests as well.
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Shipped to theaters under the code name "List After List".
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The film was originally rated R by the MPAA before being reduced to a PG-13 rating on appeal, somewhat commonplace for a James L. Brooks film.
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Paul Rudd, Kathryn Hahn, and Owen Wilson have all appeared in films or limited series based on Marvel Comics.
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Kathryn Hahn and Paul Rudd would reunite in Wanderlust (2012) and Our Idiot Brother (2011).
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Reese Witherspoon and Owen Wilson appeared in Inherent Vice (2014).
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One of three movies, along with Sweet Home Alabama (2002) and This Means War (2012), where the central plot revolves around a love triangle between Reese Witherspoon's character and two male characters. Witherspoon is also involved in love triangles with two male characters in Best Laid Plans (1999), Vanity Fair (2004), and Water for Elephants (2011), but the love triangle is not the central plot in those movies.
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Lisa wears a Washington Nationals jersey with the number 33 on the back. At the time this movie came out, there was no member of the Nationals who was assigned that number. In 2012, Edwin Jackson became the first Washington Nationals player assigned that number.
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Teyonah Parris and Kathryn Hahn both appeared in WandaVision (2021).
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Rachel Breitag's debut.
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Spoilers 

The trivia item below may give away important plot points.

When Jack Nicholson is telling Paul Rudd what's really going on, he says he feels an incredible pain in his chest, similar to how he felt when he took "Lipitor". This may be a nod to the movie Something's Gotta Give (2003) where Jack Nicholson, who portrays Harry, informs the doctor he takes Lipitor while being treated for a heart attack.
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