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| Freddie Prinze Jr. | Alfred "Al" Connelly |
| Julia Stiles | Imogen |
| Selma Blair | Cyrus |
| Shawn Hatosy | Eddie Hicks |
| Zak Orth | Monk Jablonski |
| Ashton Kutcher | Jim Morrison |
| Rosario Dawson | Lana |
| Henry Winkler | Chef Ray Connelly |
| Lucie Arnaz | Judy Connelly |
| Lauren German | Lovestruck Woman |
| Zay Harding | Young Man |
| Amanda Barfield | Faith Keenan |
| Chloe Hunter | Megan Brodski |
| Granger Green | Haley Heller |
| Jed Rhein | Gabe Stiano, New Age |
| Joseff Stevenson | Ted McGurran, Allergic |
| Elizabeth Levin | Carbs Girl |
| Lola Glaudini | Parolee |
| Robin Nance | Daddy's Girl |
| Mary Wigmore | Pearly Whites |
| Julian Michael Caiazzo | Al at 5 Years |
College coeds in New York City, Al, the son of a celebrity chef, and Imogen, a talented artist, become smitten the second they lay eyes on one another at a bar. However, the road to happiness is not a smooth one. Outside forces, including a predatory porn star who wants to lure Al into her bed, threaten to pull apart the young lovers before their romance has a chance to really flourish.
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