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Star softball player, Lisa, has just been cut from the national team; Scholarly business man, George, has just been indicted from his fathers company. With everything that they know in their lives taken from them, Lisa and George attempt to find romance. Lisas potential boyfriend, Matty, however, is as clueless and perpetually single as they come, and Georges girlfriend just dumped him. A chance hook-up through mutual friends, Lisa and George may be able to form a friendship, or more, that can help them climb out of the piles of lemons that life has handed to them.
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 womens 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 its what she really wants. As a team member, she attended therapy because it was offered as a team perk, and although stating that she didnt 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 Madisons 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 Georges problems and her own self-interest that Georges 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 Lisas life in he slowly falling for her, she the only bright spot in his life, while Lisa enjoys Georges 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.
Reese Witherspoon
Lisa
Paul Rudd
George
Owen Wilson
Matty
Jack Nicholson
Charles
Kathryn Hahn
Annie
Mark Linn-Baker
Ron
Lenny Venito
Al
Molly Price
Coach Sally
Ron McLarty
George's Lawyer
Shelley Conn
Terry
Domenick Lombardozzi
Bullpen Pitcher
John Tormey
Doorman
Teyonah Parris
Riva
Tony Shalhoub
Psychiatrist
Dean Norris
Softball Coach
Donna Dundon
Annie's Mom
Cyrus Newitt
Annie's Dad
Will Blagrove
Matty's Teammate
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