James L. Brooks is an institution. My only question over the years was whether he was the good kind of institution because there were times during I’ll Do Anything and Spanglish where I hoped a large Indian would suffocate me with a pillow and carry me away. As Good as it Gets is a movie I enjoy tremendously and his Simpsons involvement speaks for itself, but How Do You Know represented a pivotal career moment for this particular member of Hollywood royalty and a mediocre romantic comedy just wouldn’t be enough at this stage of the man’s career. Especially with the bed of talent involved. With that preface in place I am here to tell you that How Do You Know is a pretty mediocre romantic comedy.

Reese Witherspoon stars as Lisa, a Jenny Finch-alike (not a pitcher though) who after winning a gold medal for her country and various other achievements is reaching the end of her playing career. When she is cut from the next Olympic team by her coach (Breaking Bad‘s amazing Reggie Bannister clone Dean Norris, used for a pitiful one scene), she reaches a major crossroads in her life and has to decide where her life is going to go after so many years of being a professional athlete. We meet her just as she’s being set up for the bad news and the early moments involving her softball teammates and coaches had me in fear of the proceedings that lie ahead. Witherspoon has proven herself a consummate professional but I’d had a hard time buying her as a unique as a talent as much as just accepting her as a reliable consumer brand. Here she has moments where she seems to be challenging herself but buying her as a gal who really opens up when she has a pint of Guinness in her hand… no.

Paul Rudd is George, another person who has just been given bad news. Much worse news actually, as George is about to be indicted for fraud due to some sort of negligence at the corporation he works at. Immediately we see the kind of person George is as he is manhandled by his corporate lawyer (80’s sitcom star Mark Linn-Baker) and the man who runs his company, his own dad (Jack Nicholson himself, thoroughly wasted here). Even with Paul Rudd’s plentiful charisma in place, George is an absolute loser and there’s nothing worse than watching a romantic comedy where one or both of the leads are absolute wet blankets. Rudd is so good at what he does that he almost pulls it off but watching this guy be afraid of any sort of confrontation or bad news gets old fast. There’s also this really weird relationship George has with his secretary (Kathryn Hahn) that has a few cute moments and an actually heartwarming payoff but also further showcases the man as an oddball too immature and incomplete to deserve the kind fo storybook ending these films so enjoy.

The third major cog in this romantic machine is Owen Wilson as Matty, the star closer for the Washington Nationals (if this were a true story he’d be traded to a contending team by the third act). Wilson is the tasty morsel in the center of this concoction. His effortless charm and the breezy and delightfully lunkheaded superstar lifestyle he conveys adds much needed vigor to the movie. Wilson has always been a joy to watch and it’s great to see his offscreen troubles having no bearing on the unique and lovable persona he creates onscreen. When Matty is in the movie there’s a golden light shining through it, and the humor comes from Matty’s weird perception of the world from his jaded star athlete perch as well as that innocence the actor is still so good at accessing in his work. In Matty Lisa has her easy boyfriend who allows her to be frivolous and maintain ties to the athletic world she’s leaving and in her he has the closest facsimile of a real companion he’s ever had. If the film were about their relationship it may have worked.

But it’s instead about the perfect and adorable pairing of Reese and Paul and though the film doesn’t insult the intelligence it doesn’t have the pop or charm the best work of any of the involved parties had, particularly Brooks. This is the man who gave us the amazing Broadcast News and As Good as it Gets. This is most certainly not as good as it gets.

And then there’s Jack. There has never been a performer like him and his presence in a cast usually is one of if not the premier selling point. Here he is stripped of all the charm and inner fire his that has made him a one word brand, leaving only the oily core of his character. It’s a role anyone could have played and since the Brooks/Nicholson connection is a winning formula, it’s a surprise to see the actor wasted.

The film gets bogged down in subplots (it’s almost hard to watch the childbirth sequence because of how thick the sweetness is laid on), spends too much time with supporting characters, and it’s not easy to have corporate fraud and familial betrayal factor into the proceedings and maintain that peppy tone and lightness needed to make the thing feel whole. Additionally, the sweet moments and levity is effective to an extent but not enough to justify the time spent in the theater. It feels tonally off and underwritten, which is very surprising with the talent involved. And the title is too vague and just plain weak. I kept having to go back to my notes to even remember the damn thing.

How Do You Know is an uneven misfire, though I can’t imagine it’s going to be anything more than a slight hiccup for any of the involved parties.

5.5 out of 10