When 31-year-old professional softball player Lisa Jorgenson (Reese Witherspoon) is unexpectedly dropped from her team's season roster, she is left in a shellshocked personal crisis. For a focused, driven athlete like herself, she suddenly is put in the position of having lost what she loves the most and not knowing what to do with the rest of her life. Across town, George Madison (Paul Rudd) is an earnest, nice-guy corporate executive who can't believe it when he becomes the target of a federal tax fraud investigation. Having been dumped by his girlfriend and facing newfound unemployment of his own, he feels all the more betrayed when he learns his boss and father Charles (Jack Nicholson) has been up to some unsavory company activities behind his back. The day couldn't get any worse, so Lisa and George figure there's no sense in cancelling their blind date. Their dinner starts off rocky—both of their nerves are on edge—but when Lisa suggests they just sit silently and eat without the pressure of idle chit-chat, George is instantly smitten.

Written and directed by James L. Brooks (2004's "Spanglish"), "How Do You Know" is an overstuffed romantic comedy that can never quite seem to find its focus. Spending too much time on extraneous subplots—all of the corporate governance material with George, his faithful and very pregnant assistant Annie (Kathryn Hahn), and his crooked father drones on endlessly without even the satisfaction of a payoff—and foregoing substantial character development for a lot of back-and-forth squabbling between people who can't make up their minds, the film is often frustrating in its dumbed-down repetitiveness. The idea of two people separately and simultaneously stripped of their professions and wondering what's next for them as they navigate a romantic relationship is conceivably interesting, but Brooks tarnishes the results by resorting to narrative conventions while failing to properly explore his characters with the detail and care they should be given. Instead, they're at the mercy of a screenplay that washes, rinses and repeats contrived conflicts so that the running time prattles toward the two-hour mark. In the end, it just doesn't add up to anything that hasn't been seen before, and done with more style and energy.

It has been noted that filmmaker James L. Brooks created the character of Lisa Jorgenson expressly for Reese Witherspoon (2008's "Four Christmases"). The question, then, becomes why he didn't write the role with more depth and intelligence. Lisa is one of the two central leads, but she is gravely underdeveloped with no mention of parents or a family, no talk of her background outside of her softball playing, and no true attention paid to the steps she begins to take—or at least begins to talk about—in order to make a new career path for herself. Furthermore, for someone who prides herself on being strong and taking an initiative in things, she is awfully wishy-washy in her decision-making. No fault of Witherspoon's, who makes the most of the role and is as lovely and beguiling as ever, poor Lisa is used and abused by the script, becoming a pawn knocked back and forth by the requirements of the plot. It is blatantly apparent that George is the man who is right for her, yet it never seems to even occur to her. Instead, she treats George like a gay best friend, seeking his shoulder to lean on every time she has a falling-out—which is repeatedly—with boyfriend Matty (Owen Wilson), a Washington Nationals pitcher who is unashamedly insensitive about what it means to be in a monogamous relationship.

As the sincere George, Paul Rudd (2010's "Dinner for Schmucks") is even more charming here than usual—quite a feat—so it's easy to imagine how a really good love story could have been made between himself and Reese Witherspoon. "How Do You Know" keeps them apart emotionally for way too long as Lisa makes wrong decisions and overlooks the obvious. One of the film's best scenes is the already-mentioned initial dinner date they share, their personalities and chemistry bouncing off one another even when things fall silent and they simply have their meals together. Too much time is spent after this wandering off-track with the ins and outs of George's business woes.

Matty, too, overstays his welcome. A professed ladies' man whose luxury bathroom comes with a drawer of sealed toothbrushes and a closet of women's sweats in all sizes for his overnight guests, Matty's behavior turns off Lisa at first, but then she gravitates toward it. She believes she can change him, but is just fooling herself. Nevertheless, Lisa gets angry and walks out on him numerous times, only to return for no plausible reason. This does a distinct disservice to her character, whom the viewer almost begins to lose respect for. As Matty, Owen Wilson (2008's "Marley & Me") doesn't play the part as a bad guy, but as the wrong guy. We know it, and George knows it. Even Matty probably knows it deep inside. As for Lisa? Well, let's just say she's not the sharpest knife in the drawer when it comes to ways of the heart.

"How Do You Know" was reportedly made for $120-million, an offensively bloated number for what reminds of a stage play and could have just as easily been filmed with unknown actors for less than a million. Surely everyone was overpaid—this includes Jack Nicholson (2007's "The Bucket List"), showing up in a half-dozen forgettable scenes and wasted beyond description as George's dad—because there is no other explanation for so much money having been spent. The picture features very few establishing shots. Scope is minimal. There is no effects work; the film is all about people standing around conversing. There aren't even any songs on the soundtrack that might have cost a lot; actually, the only music heard is the low-key score by Hans Zimmer (2010's "Inception"). By the time Lisa comes to her senses and begins noticing all that's right for her about George and all that's not about Matty, there is just enough time for a closing ten minutes that are winning and tender. Sadly, it arrives too late to mend the deficiencies of the previous 100 minutes. "How Do You Know" doesn't really know the answer to its title question; it doesn't trust its characters enough, most specifically Lisa, to find out.