The story brings romance and courtship into the electronic age of the World Wide Web via e-mail and chat rooms.
Joe Fox (Hanks) and Kathleen Kelly (Ryan) live and work blocks from each other on New York City's Upper West Side. Their lives are practically intertwined. They both shop at the same place, frequent the same coffee shop, and even own competing bookstores on the same street. They also both have significant others of their own. Joe has the overly hyper book editor Patricia Eden (Parker Posey), while Kathleen lives with the scholarly newspaper columnist Frank Navasky (Greg Kinnear). Then they meet in a chat room.
Though they keep their identities secret (they're known only by screen names "NY152" and "Shopgirl"), they tell each other everything about their lives, including their private feelings, which slowly turn into affection for each other. When Joe decides to open a new branch of his "Foxbooks" chain that risks putting Kathleen's "Shop Around the Corner" out of business, the tension between them escalates. Surely her boutique business will be lost to the conglomerate with a built-in newsstand and coffee bar. When Joe sees Kathleen waiting for him in the restaurant where they agreed to meet up, he puts two and two together, but cannot face her, given their agreement not to reveal each others' names and professions. How can he reveal himself to her now, knowing that he is the cause of her misery? Hopefully, love will conquer all.