Teenager Holly Hamilton (Hilary Duff) is tired of moving every time her single mom Jean (Heather Locklear) has another personal meltdown involving yet another second-rate guy. To distract her mother from her latest bad choice, Holly conceives the perfect plan for the perfect man, an imaginary secret admirer who will romance Jean and boost her shaky self-esteem. When the virtual relationship takes off, Holly finds herself having to produce the suitor, borrowing her friend's charming and handsome Uncle Ben (Chris Noth - Sex and the City) as the face behind the e-mails, notes and gifts. Holly must resort to increasingly desperate measures to keep the ruse alive and protect her mom's newfound happiness, almost missing the real perfect man when he does come along.