When Ben Martin e-mails Chloe Andersen, a beautiful mystery girl who keeps crossing his path, he sends a message to single mother Charley Anderson by mistake.
The story of Charley Anderson, a single mother, and Ben Martin, a man who began an e-mail relationship with her, thinking she was another woman.
A young man named Ben Martin (Sean Patrick Flanery) falls for a beautiful girl who crosses his path but winds up emailing his 'love notes' to a single mother instead. He dates the first girl but finds out that she is not the person he had communicated and fallen in love with online.
Ben Martin has a case of "love at first sight" when he sees a beautiful woman in a cafe and overhears Chloe Andersen giving her email address to a friend. Later that night, Ben courageously breaks the ice by introducing himself to Chloe anonymously via email with this message: "Five Top Reasons Why I'm Your Secret Admirer." But, Ben's display of affection for Chloe is misfired when his emails are instead delivered to Charley Anderson. It seems Chloe's co-worker shares a similar email protocol at Game 1 Sports and Entertainment Marketing owned by the legendary sports star "Big-Jim" Nelson. Charley, an overworked single mom who hit the delete button on romance long ago, now excitedly turns on her computer. Soon Ben begins dating Chloe, but she never quite lives up to the anonymous e-mail relationship and innocent friendship he develops with Charley.