Lindsey (Drew Barrymore) is an ambitious business consultant, approaching "twenty-ten", whose spirit is as luminous as her beauty. High-school teacher Ben (Jimmy Fallon) is a good catch. He's charming, funny and great with kids, but has a small income. Sure, they have their differences. She's a workaholic; he loves his summers off, but when they first meet, and despite their differences, their attraction is immediate and true love overcomes all. Everything is wonderful, and Ben seems to be the man of her dreams, until Lindsey discovers what a 23 year long obsession with his favorite team really means. Together they must decide if they will strike out or fight to keep love alive