06/04/2005
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
Evan Helmuth
as Troy
Johnny Sneed
as Chris
Greta Onieogou
as Tammy
Lizz Alexander
as Charlene
Brandon Craggs
as Casey
Shary Guthrie
as Christie
Lenny Clarke
as Uncle Carl
Steve Levy
as Reporter at Spring Training
Scott Severance
as Artie
Jessamy Finet
as Theresa
James B. Sikking
as Doug Meeks
Willie Garson
as Kevin
Armando Riesco
as Gerard
Zen Gesner
as Steve
Mark Andrada
as Ezra
Matt Watts
as Valet
Charlotte Sullivan
as Spin Instructor
Tim McCarver
as Tim McCarver
John Franchi
as Red Sox Fan
Don Gavin
as Cop
Stephen King
as Stephen King (uncredited)
Nicholas Purcell
as Red Sox Fan (uncredited)
Andrew Wilson
as Grant Wade
Martin Roach
as Husband
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