Plot: Lisa Jorgenson and George Madison simultaneously face major life altering events. Thirty-one year old Lisa, long the emotional center of the national Softball USA women's team, is cut as she was hitting the twilight of her playing life without she even realizing it. As such, she made no plans, like many of her teammates, for her post-softball life, she, not knowing what to do, mimicking the path of the other players without any thought if it's what she really wants. As a team member, she attended therapy because it was offered as a team perk, and although stating that she didn't believe in it, she has ended up over-analyzing everything arguably because of what she learned in therapy. George, a high powered executive in his father Charles Madison's company, is a straight up kind of guy who would not knowingly do something wrong. It is in his misassumption that others, including his colleagues, also do the right thing that he learns he is being investigated for securities fraud, his only wrongdoing being trusting his colleagues. Due to the legalities, the Board of the company recommends not only not having contact with George, but not providing him with information concerning their internal machinations in dealing with the investigation and not providing him any in-house legal counsel, with only his father and his loyal secretary, Annie, standing by him, albeit necessarily from a distance. It is because of George's problems and her own self-interest that George's girlfriend breaks-up with him, the break-up just after they decided to take their relationship to the next level. It is under these circumstances, arguably the worst day in their respective lives, that Lisa and George meet on a delayed and what turns out to be a disastrous blind date. However, in his emotional agony over his legal problems, George sees something special in Lisa. The next time George and Lisa meet in unexpectedly running into each other, Lisa has ended up entering into a relationship with Washington Nationals pitcher Matty Reynolds. While Matty is outwardly caring, he also is insensitive and immature, probably the result of living in the bubble of his life of wealth and fan adulation. Lisa is able to justify one insensitive comment or action by Matty after another in her analyzing the situation after the fact. George tries to remain a part of Lisa's life in he slowly falling for her, she the only bright spot in his life, while Lisa enjoys George's company especially as a respite from problems with Matty. What George ends up doing with regard to Lisa is in light of his legal problems and figuring out where those legal problems were initiated.
Alternative Plot: Lisa Jorgenson's (Reese Witherspoon) entire life has been defined by softball, but at 31, she is deemed too old to play and cut from the team. After being cast adrift, she begins a fling with Matty (Owen Wilson), a charming womanizer who plays professional baseball. About the same time, she goes on a blind date with George (Paul Rudd), a businessman on the hook for stock fraud. Caught in a romantic triangle with the two men, Lisa ponders the meaning of love.
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