The film was shot in Philadelphia and Washington, D.C.. It was the third film to feature Witherspoon and Rudd following 1998’s Overnight Delivery and 2009’s Monsters vs. Aliens. How Do You Know was released theatrically on December 17, 2010, and grossed $48 million against a $100 million net budget.
Softball player Lisa Jorgenson is devastated when she is left off the Team USA roster. Unsure what to do next, Lisa begins dating Matty Reynolds, a pitcher for the Washington Nationals. She also receives an intriguing phone call from a young executive, George Madison, who was advised by a friend of Lisa's to give her a call. George calls out of politeness because he wants to explain that his relationship with his girlfriend has just become more serious. But life takes an abrupt turn for the worse for George when he suddenly finds himself the target of a federal criminal investigation for corporate malfeasance at a company run by his father, Charles Madison. George is fired from his job and abandoned by the company, with the exception of his father and his pregnant secretary, Annie.
Still reeling from this blow, George goes to his girlfriend for sympathy and is stunned when she immediately breaks up with him. On a whim, George calls again to invite Lisa to dinner and she accepts. It turns out to be a disaster; George is so overwhelmed with his troubles that Lisa eventually asks that they just eat in silence, and they part ways not expecting to see one another again. Soon, Lisa moves in with Matty, who has a penthouse in the same upscale building where George's father lives. Matty is rich, well-meaning and fun, but is also immature and insensitive, and continues to have casual affairs with other women.
George is indicted and could face prison time. Annie is so loyal that she tries to give him inside information in advance, but he urges her not to lose her own job. Matty tries to do better in Lisa's eyes, promising to consider seeing fewer women on the side. He inadvertently offends her, so Lisa moves out and spends a pleasant, tipsy evening at George's modest new apartment. George's father then drops one last bombshell on his son: It was he who committed the illegal act for which George is being charged. Due to a previous conviction, Charles would spend at least 25 years — basically, the rest of his life — in prison, whereas George would only do three years at most.
On the night Annie's baby is born and her boyfriend proposes, Lisa begins to reconsider her previous reluctance to settle down. George is clearly smitten with her, but Matty pleads for another chance and she accepts. George makes a proposition to his father: He will take one more shot at persuading Lisa to be with him; If she will, Charles must go to jail, and if she won't, George will take the rap for his dad. At a birthday party that Matty throws for her, George confesses his feelings for Lisa and goes outside to give her time to think it over, Charles looking on from above. Finally, Lisa says goodbye to Matty and joins George outside. At the end of the movie, they are seen boarding a bus together.Reese Witherspoon as Lisa Jorgenson
Paul Rudd as George Madison
Owen Wilson as Matty Reynolds
Jack Nicholson as Charles Madison
Dean Norris as Tom
Kathryn Hahn as Annie
Yuki Matsuzaki as Tori
Andrew Wilson as Matty's Teammate
Shelley Conn as Terry
Tony Shalhoub as Psychiatrist
Domenick Lombardozzi as Bullpen Pitcher
Ron McLarty as George's Lawyer
Lenny Venito as Al
Mark Linn-Baker as Ron
Molly Price as Coach Sally
Bill Murray was Brooks' original choice for the role of Charles Madison.
Brooks began work on the film in 2005, wishing to create a film about a young female athlete. While interviewing numerous women for hundreds of hours in his research for the film, he also became interested in "the dilemmas of contemporary business executives, who are sometimes held accountable by the law for corporate behavior of which they may not even be aware." He created Paul Rudd's and Jack Nicholson's characters for this concept. Filming finished in November 2009, although Brooks later reshot the film's opening and ending. The total production cost of the film was $120 million, with the net budget at about $100 million after tax rebates from Pennsylvania and the District of Columbia. The combined salaries for the director Brooks (about $10 million) and the four major stars Witherspoon ($15 million), Nicholson ($12 million), Wilson ($10 million) and Rudd ($3 million) totaled about $50 million. Brooks' "slow and meticulous" production and post-production also explained the size of the budget.
How Do You Know opened at $7.6 million in the United States and Canada, making it eighth in the box office at its first weekend. The film fell off the chart by its third weekend. On its opening day, December 17, 2010, it debuted at #5 behind Tron: Legacy, Yogi Bear, The Fighter and The Chronicles of Narnia: The Voyage of the Dawn Treader. By December 22, it was #11 in the box office. How Do You Know grossed a total of $48,668,907 worldwide. In 2014, the LA Times listed the film as one of the biggest box office flops of all time.
On Rotten Tomatoes, the film has an approval rating of 32% based on 147 reviews and an average rating of 4.9/10. The site's critical consensus reads, "How Do You Know boasts a quartet of likeable leads – and they deserve better than this glib, overlong misfire from writer/director James L. Brooks." Metacritic reports a score of 46 out of 100 based on 38 critics, indicating "mixed or average reviews". Audiences polled by CinemaScore gave the film an average grade of "C-" on an A+ to F scale.