To understand the student experience on social software, the research aims to explore the disruptive nature and opportunity of social networking for higher education. Taking four universities, the research: (1) identifies the distinction between the students’ current usage of social software; (2) reports on the students’ experience on opportunities and challenges of learning with social software; and (3) introduces principles as a guideline in using social software for learning. Quantitative research methods (web-based questionnaires) were incorporated to investigate the pattern of learners’ usage. Qualitative methods (student interviews) were adopted to clarify and further inform this relationship and their attitudes towards social software for learning. The results demonstrate a massive use of educational technology with distinct divide between the learning space and personal space. Student voices reveal that the central problem of such divide is due to the contrast perception and experience of ‘learning/studying and social life’. We argue that online learning and social personas may overlap but that learning needs to be designed so that it addresses the individual preferences to combine or separate the two domains. The paper concludes with a few principles of learning with social software grounded in students’ experience and Vygotsky’s paradigm.