A transplanted New Yorker attempting to acclimate to Los Angeles, Mike Peters (Jon Favreau), 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 (Vince Vaughn), 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 (Heather Graham), sparking a welcome new romance.