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| Jon Favreau | Mike Peters/$5 Winner |
| Vince Vaughn | Trent Walker/$100 Gambler |
| Ron Livingston | Rob |
| Patrick Van Horn | Sue |
| Alex Desert | Charles |
| Deena Martin | Christy |
| Katherine Kendall | Lisa |
| Brooke Langton | Nikki |
| Blake Lindsley | Girl With Cigar |
| Heather Graham | Lorraine |
A transplanted New Yorker attempting to acclimate to Los Angeles, Mike Peters, is struggling to both boost his comedy career and get over his last relationship. A self-proclaimed master of seduction, Mike's buddy, Trent Walker, tries to show him how to make connections and get the attention of women. Slowly moving toward regaining his confidence, Mike meets the gorgeous and down-to-earth Lorraine, sparking a welcome new romance.
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