How Do You Know

Softball player Lisa Jorgenson 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. Lisa is devastated when she is left off the Team USA roster. On a whim, George calls again to invite Lisa to lunch 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. Unsure what to do next, 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. George and Lisa bump into each other in Matty’s building and George offers to help Lisa carry her groceries home. Matty returns home and is upset to find Lisa at “his place” with an uninvited guest. 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 due to his advanced age — 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 does, Charles must go to jail, and if she doesn'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 tells her to meet him downstairs if she decides she reciprocates them too. George then leaves the party and goes downstairs to give her time to think it over. Finally, Lisa says goodbye to Matty and joins George outside. Charles looking on from above smiles at the sight, but the smile soon fades as he realises that he has to go to jail.

Lisa is confused about her feelings and tells George, "I thought you were this silly guy. Now it's like... everything but you seems silly." George suggests she had never felt the kind of overwhelming love where the guy is the whole deal, which helps her realise that she's in love with him. Lisa then reaches out and holds George's hand and they are seen boarding a bus together.

Bill Murray was Brooks' original choice for the role of Charles Madison.[5]

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.[6] Filming finished in November 2009,[7] although Brooks later reshot the film's opening and ending.[3] 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.[3]

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.[8] 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 $48.7 million worldwide.[4] In 2014, the Los Angeles Times listed the film as one of the biggest box office flops of all time.[9]

On Rotten Tomatoes, the film has an approval rating of 31% based on reviews from 151 critics, with an average rating of 4.88/10. 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."[10] On Metacritic it has a score of 46 out of 100 based on reviews from 38 critics, indicating "mixed or average reviews".[11] Audiences polled by CinemaScore gave the film an average grade of "C-" on an A+ to F scale.[12]

Todd McCarthy of The Hollywood Reporter gave it a mixed review, and called it "A low-impact romantic comedy-drama from James L. Brooks in which the central characters are strangely disconnected from one another as well as from the audience."[13] Peter Debruge of Variety gave it a negative review, and wrote: "How do you know when the spark is gone? When your latest romantic comedy looks like TV, feels like greeting-card poetry and sounds like a self-help manual."[14] Roger Ebert of the Chicago Sun-Times wrote: Nothing heats up. The movie doesn't lead us, it simply stays in step.[15]

Richard Corliss of Time magazine, noted that the film had already received particularly negative reviews, but responded "Yeah, well, I still like the film."[16]

• Official website
• How Do You Know at IMDb
• How Do You Know at Box Office Mojo