Conducting a dialogue on the Web is a matter of linking thoughts in digital conversations. This article is intended to contribute toward learning qualities in such conversations. The term “dialogue” refers to a special kind of conversation, having structure, purpose, and learning qualities. The focus is on learning Web dialogues taking place in a course context using text-based, asynchronous meetings. An overview of factors that influence digital group conversations is presented together with a model for dialogue competence face-to-face. The dialogue potential of Web dialogues is highlighted. Course leaders and teachers wanting to create opportunities for learning Web dialogues, as well as the interlocutors themselves, need to wise up on the digital interchange of thoughts as a form.