Lisa (Reese Witherspoon) and George Madison (Paul Rudd) are both nice people and team players. And that is why they end up on a horrible date on what is for each of them the worst night of their lives.

It’s the worst night because both of them have been cut from their teams. That’s literally the case for Lisa, a 31-year-old professional women’s softball team. Being the hardest working and most supportive player is not enough when she’s a second slower getting to first base than she used to be. She makes everyone around her better. “The intangibles are everything,” urges the assistant coach. But they don’t score runs. The upbeat little post-it note aphorisms Lisa has covering her bathroom mirror do not provide any guidance. They can remind her to be determined, but she is no longer clear on what she should be determined about. And although she tells her sort of boyfriend, a player for the Washington National baseball team (Owen Wilson) that she doesn’t want to talk about her feelings, she is a little disconcerted when he tells her that is his preference.

George, a top executive at a corporation founded by his father (Jack Nicholson), has been informed by the company lawyer that he is under investigation and on his own in finding and paying a lawyer to defend him from possible fraud charges. And his girlfriend, a physics professor, dumps him with cheery efficiency. It is a lot to process. And he doesn’t want to process it. So, why not call that blind date prospect he had put aside when he thought he had a girlfriend?

As terrible as the date is — they ultimately decide that it is better they don’t speak at all — they sort of enjoy it. And we do, too, because writer/director James L. Brooks (“Broadcast News,” “Terms of Endearment,” “As Good as It Gets”) is very good at exactly that: showing us a world of flawed people dealing with messy, complicated, and painful challenges in a manner that draws us in and keeps us on their side.

There is a lot that does not work. It completely fails in portraying with two subjects I know very well: securities law (note, Mr. Brooks, that’s “securities” plural — “security law” is more like TSA pat-down challenges) and Washington D.C. (no place in Washington is an hour and ten minutes from any other place, even on the bus). George’s father is a character even Jack Nicholson can’t make anything more than a highly artificial narrative inconvenience. The magnificently talented Kathryn Hahn (please, someone give her a worthy role) does her best in a part that is both over- and under-written as George’s very pregnant and very loyal secretary. One of the big turning-point speeches doesn’t deliver the punch it sets us up to expect.

A lot of people are not going to like this movie. But I did because for me he got a lot right. Audiences expecting a conventional structure and tone will be disappointed. I like a movie that is, like its leads, endearingly messy and subverts our genre expectations. Brooks colors outside the lines. There is more happening around the edges of this movie than happens in the middle of the screen of most — George’s problem is more than just a topical reference. And the difference between a male and female professional athlete is not addressed; it’s just there.

Brooks’ dialogue is always a great pleasure. Rudd, one of the most engaging of actors, has never been better. Watch his face carefully in the elevator scene, when he thinks his world has collapsed and then looks up to see that the girl from the awful silent date is there. The mixture of emotions is superbly handled. Witherspoon is revelatory as a woman who relied on an all-encompassing structure with answers for everything and now realizes there were questions she did not even know she had. And if that makes us question our own conventional notion of what we know, well, it just shows you that the intangibles really are everything.