When Ben Wrightman, a young teacher, begins dating pretty businesswoman Lindsey Meeks, the two don't seem to have a lot of the same interests, but they fall in love, regardless. Their romance goes well until baseball season begins, and Lindsey soon realizes that Ben is completely obsessed with the Boston Red Sox. Though she tries to understand Ben's passionate team loyalty, eventually it threatens to end their otherwise happy relationship.
Drew Barrymore
as Lindsey Meeks
Jimmy Fallon
as Ben Wrightman
Jason Spevack
as Ben - 1980
Jack Kehler
as Al
Maureen Keiller
as Viv
Daniel Greene
as Waiter
Ione Skye
as Molly
Marissa Jaret Winokur
as Sarah
KaDee Strickland
as Robin
JoBeth Williams
as Maureen Meeks
Siobhan Fallon Hogan
as Lana
Brett Murphy
as Ryan
