Director James L. Brooks returns to the helm for this ensemble comedy starring Reese Witherspoon, Jack Nicholson, Paul Rudd, and Owen Wilson, which centers on the story of a passionate athlete who finds herself romantically torn between a narcissistic baseball star and a straight-laced businessman. As far back as Lisa (Witherspoon) can remember, her life has been defined by sports. Then, in the blink of an eye, she's cut from the team. With her identity in crisis as she attempts to regain her footing in life, Lisa begins dating Matty (Wilson), a Major League Baseball pitcher and notorious womanizer. Meanwhile, terminally honest businessman George (Rudd) finds himself on the road to financial ruin or worse after being wrongly implicated in a financial crime. As George struggles to clear his name and reconcile his turbulent relationship with his father, Charles (Nicholson), a chance meeting with Lisa at the lowest point in both of their lives leaves him optimistic that things may work out after all. Meanwhile, Lisa and George both realize that the only thing that's certain about the future is that we never know what fate has in store for us.
by Jason Buchanan synopsis