

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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