Brad is about to hook up with the girl of his dreams, but runs into a problem, no condom. So Brad sets out into the night to find one, running into many obstacles along the way, while not knowing his best friend, Leah is in love with him.
| Actor | Role |
|---|---|
 Will FriedleBrad Kimble | Brad Kimble |
 Jennifer Love HewittLeah Jones | Leah Jones |
 Marley SheltonBrooke Kingsley | Brooke Kingsley |
 Danny MastersonSeth | Seth |
 Jason MarsdenJosh | Josh |
 Eric BalfourKyle | Kyle |
 Jennie KwanTrish | Trish |
 Charlotte AyannaNina | Nina |
 Kathy GriffinCashier | Cashier |
| JJulien CesarioHomeboy | Homeboy |
 Mike MoroffBig Brother | Big Brother |
 David Patrick KellyBagman | Bagman |
 Anthony Michael HallBus Driver | Bus Driver |
 Paulo TochaJanitor | Janitor |
 Danny TrejoScarface | Scarface |
 Lobo SebastianLead Homeboy | Lead Homeboy |
 Alicia ArdenGirl in Video | Girl in Video |
 Mary McCuskerMom | Mom |
 Chauncey LeopardiFreshman | Freshman |
 Tito LarrivaTattoo Man | Tattoo Man |
 Aaron LohrJock #1 | Jock #1 |
 Allan GrafLenny | Lenny |
 Steve ValentinePonytail Guy | Ponytail Guy |
 Wendy WorthingtonJowly Clerk | Jowly Clerk |
 Lee MajorsOfficer Austin | Officer Austin |
 John FinnBen Kimble | Ben Kimble |
 Wendie MalickBeverly Kimble | Beverly Kimble |
| CChristine DeaverLatin Mama | Latin Mama |
| JJoe CerranoBiggest Homeboy | Biggest Homeboy |
| BBradford DrazenEmployee | Employee |