Lisa (REESE WITHERSPOON) is a professional softball player who's been a jock most of her life to the point that she only dates other athletes. Her latest boyfriend is Matty (OWEN WILSON), a professional baseball player who's confident in his womanizing ways, but thinks he might be falling for Lisa and thus asks her to move in with him.
Corporate man Charles (JACK NICHOLSON) also lives in that same building, but his focus is on a federal subpoena that's been served to his adult son, George (PAUL RUDD), who runs the daily operations of their company but is surprised by the charges leveled against him. The same holds true for his very pregnant but single assistant, Annie (KATHRYN HAHN), who doesn't like the way Charles treats George.
Having been set up on an unscheduled blind date by her friend and fellow player, Lisa ends up going to dinner with George, but with his confidence shaken, he doesn't make much of an impression on her. Then again, when she's cut from her team, she ends up in the same boat. From that point on, and despite wanting to remain as Matty's girlfriend, Lisa must choose between him and George and the various bits of emotional and behavioral baggage they bring to the romantic quandary.