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Jack Nicholson, Reese Witherspoon, Owen Wilson, and Paul Rudd in How Do You Know (2010)

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How Do You Know

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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.
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.
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.
Kathryn Hahn - who plays a pregnant character in the film - was pregnant in real life when she got the part.
James L. Brooks worked on the film for over 5 years.

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