In this romantic comedy, we follow the story of Lisa, a young softball athlete who, after a painful breakup, finds herself at a crossroads in her life. Lisa, played by Reese Witherspoon, feels lost and begins to question what love and happiness really mean. Her life takes an unexpected turn when she meets George, a company executive who faces his own legal and personal issues. Paul Rudd brings to life this sweet and awkward character, who tries to find a balance between his professional life and his emotional life.
Meanwhile, George's father, a business tycoon portrayed by Jack Nicholson, is dealing with the consequences of his past decisions, which further complicates the situation. The chemistry between Lisa and George develops amidst a tangle of emotions, where both must navigate the insecurities of modern love, the pressure of expectations, and their own doubts.
The comedic twists arise when Lisa's friends try to guide her on her path to love, as she grapples with her new connection to George and her former life. As relationships evolve and doubts surface, Lisa must decide whether she can take the risk of opening her heart again or if it’s easier to cling to the familiar. Ultimately, the film explores the quest for truth in love and how past decisions can influence the future.