New York City, May 2000. The Internet bubble has burst and Evan, a computer programmer, is fired with an email from his boss. The next day, his girlfriend dumps him, also via email. Afraid to check any more emails, Evan desperately seeks a rebound romance but the catastrophes that ensue go from bad to hilariously worse. 
Fortunately, Evan meets Sammy — someone whose legendary disasters with females eclipse even his own. To reverse their fortunes, they recruit their friends — Trevor, Yi, and Carlos — to form a group of five guys who take on Manhattan in pursuit of dates, sex, and adventure. 
When Evan, a closet writer, falls desperately in love with a Hollywood starlet, he schemes to meet her by writing a novel that will sweep her off her feet. Sammy knows nothing about publishing but is confident of one thing: Evan's book should have the word "sex" in the title. 
With musings about life, relationships, and human psychology, this quintessential New York story about the search for happiness follows five men on their comical paths to trouble, self-discovery, and love.