Nadine (Janeane Garofalo), a quirky entrepreneur, owns a dating service that is failing. She realizes that getting a date isn't the hard part, but getting through the date is. She decides that what singles really need is a dating "coach." Nadine develops a "fool-proof" dating guide that will guarantee anyone love. But, in order to be credible and save her business she must become her own client and win the love of one of the city's most eligible bachelors.
The trouble is... she too has been unlucky in love. But...Nadine is determined to prove her faith in her new manifesto as she embarks on a mission of extreme dating and using any means necessary to get her man.