Kathleen runs a small mom and pop bookstore known as the Shop Around the Corner. This name pays homage to the earlier movie The Shop Around the Corner that You've Got Mail is based on loosely. In You've Got Mail Kathleen watches as she loses her business and her customers to the new super bookstore chain run by Joe Fox. While this is happening she is having trouble with her current boyfriend and engages in cyber flirtations online with a mysterious stranger whom is actually Joe Fox even though she does not know it.

Joe is the man with the plan, he runs a succesful bookstore chain and aims to drive Kathleen Kelly's little store out of business to make way for progress which is found in his new super stores. He even checks out his competition and makes a purchase from Kathleen's stores, her prices amaze him as they must be high to help compensate for the fact she sells few books. Joe is having troubles with his girlfriend and engages in a cyber romance with Kathleen. He realizes who is cyberdate is before Kathleen does and enjoys planning a meeting with Kathleen, his Shopgirl.

This is Joe Fox's girlfriend at the start of the film. Joe dumps her after being trapped in an elevator. There he has time to reflect on how unpassionate his girlfriend is.

This is Kathleen's boyfriend at the start of the film. He ultimately is dumped by Kathleen so that she can pursue her cyberman without guilt.

This is Kathleen's old friend whom she confides much in. Birdie has been around since Kathleen's bookstore was first started years ago.