The very talented Paul Rudd plays George, son of Charles (Nicholson) who is the target of a federal investigation after his father sets him up by falsifying corporate financial documents. The problem is George is a really nice, honest guy and Charles is a lying scumbag who would throw his son to the federal wolves.
In a seemingly unrelated story, Reece Witherspoon plays Lisa, a very talented softball player with an incredible track record and evidently serious skills. She gets cut from the Olympic team because of her advancing age (she will be 31 at the next Olympics). Lisa is dating Matty, played by Owen Wilson. Matty is a $14 million per year major league baseball player, who is also a player off the field.
Everyone in this story is so very nice, but screwed up in their own way. That's actually a hopeful start. So one thing leads to another and George falls for Lisa. Lisa moves in with Matty, who lives in the Charles' building. Lisa then moves out. George is always there for Lisa while her life is in shambles. George's life is in shambles too, but all he cares about is Lisa. Any guess how this ends up? Of course you know. This script is not built for surprises. Or romance. Or comedy.
The bulk of the comedy comes from a very pregnant Kathryn Hahn as Anne, whose life is also a bit of a mess. She is an unmarried, pregnant assistant to George, who worries about him, her and everything ... but she has such a big heart that she bakes and labels multiple dinners for George.
Anyway ... the best part of the film is that we never get subjected to Owen Wilson throwing a pitch or Reese Witherspoon actually playing softball. There is so much talent associated with this film, but it definitely proves the point that the heart of a film is not in the direction or the acting, but in the script. For a similar story line, but far superior film, go re-watch When Harry Met Sally for the eighteenth time. It has comedy and romance and a worthy script.