Lisa (Reese Witherspoon – Legally Blonde) is in the middle of a life-crisis. Her position on the US Softball team has just gone and she’s now forced to re-evaluate her goals. She has just started seeing megastar Baseball player Matty (Owen Wilson – Marley & Me) and is enjoying her time with him until a friend fixes her up on a blind date with George (Paul Rudd – Clueless). He is in the middle of his own life-crisis and is being investigated for financial fraud even though he’s innocent. With all their troubles, perhaps Lisa and George can help each other forget their woes? But when George falls for Lisa that complicates matters further and sparks a rivalry for her affections.