Ryanisawomanizingstockbrokerwhoseunethicalbusinesspracticescosthimhisjobandhistrader'slicense.Unabletofindanotherjob,heisforcedtomoveinwithhisequallyself-involved(andcompletelyoblivious)girlfriend,Cindy,aninsensitiveadvicecolumnistonthecuspoflosingherownjobduetoherpooradviceandslowworkhabits.Findingthatthetruthbehindhismovinginhasnothingtodowithromance,Cindyrunsoffwithanotherman.RyandecidestostayintheapartmentandearnalivingbydoingCindy'sjob.RyanestablisheshimselfwithCindy'seditor,Page,asCindy'sgo-fer,collectingCindy'spaychecksandmailanddeliveringhercolumns.InitiallyashopelesslyineptasCindyingivingadvice,henearlygetsthecolumncanceled.However,herapidlygrowsintothejobandthecombinationofforcedintrospection,researchandthegrowingknowledgethatheistouchingotherpeople'slivestransformshim.Thecolumnbecomesanamazingsuccess.RyanfindshisinitiallysuperficialattractiontoPagegrowingintolove,buthecannotrevealhisfeelingswhileheisadeceptivefraud.Meanwhile,Cindybecomesawareofhergrowingfame,andreturnstocashin,atthesametimethattheownerofarivalnewspaperchainattemptstoforcePagetosellCindy'scolumntohim.