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| Drew Barrymore | Lindsey Meeks |
| Jimmy Fallon | Ben Wrightman |
| James B. Sikking | Doug Meeks |
| JoBeth Williams | Maureen Meeks |
| Willie Garson | Kevin |
| Evan Helmuth | Troy |
| Ione Skye | Molly |
| Jason Spevack | Young Ben |
| Jack Kehler | Al |
| Scott Severance | Artie |
| Jessamy Finet | Theresa |
| Maureen Keiller | Viv |
| Lenny Clarke | Uncle Carl |
| Johnny Sneed | Chris |
| Michael Rubenfeld | Ian |
| Brett Murphy | Ryan |
| Brandon Craggs | Casey |
| Isabella Fink | Audrey |
| Darren Frost | Zach |
| Zen Gesner | Steve |
A corporate executive falls for an affable schoolteacher obsessed with the Boston Red Sox.
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