With Valentine’s Day approaching, Eve Lovett (Joely Fisher), a workaholic TV talk show host with a string of failed relationships, is worried she will never find true love. But when a mysterious stranger named Vernon Gart (Jamie Kennedy) shows up on the set claiming to work for Cupid, Inc., Eve has no idea her love life is about to get an arrow right through the heart.

To help boost the show’s low ratings, Eve's handsome producer Rick (Roark Critchlow), books Vernon as a love expert to do a segment called “Eve’s Week of Love.” Eve reluctantly takes Vernon up on an very unusual offer--if she can help one couple fall in love before Valentine’s Day, her own true love will be revealed. Eve begins enthusiastically setting up couples, but through a series of matchmaking mishaps, her deadline is soon up. Will cupid’s arrow hit his mark or is Eve destined to be alone forever?