New York City, May 2000. The Internet bubble has burst, and Evan's boss fires him with an email. 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 someone whose legendary disasters with females eclipse even his own.

To reverse their fortunes, they recruit their friends into a group of five guys who take on Manhattan in pursuit of dates, sex, and adventure. 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.