The World Wide Web celebrated its 25th birthday in 2014. In those 25 years, the Web has evolved from static websites (Web 1.0) to a highly complex dynamic system (Web 3.0) with health information processing one of the primary uses. Until now, the western biomedical paradigm has been effective in delivering healthcare, but this model is not positioned to tackle the complex challenges facing healthcare today. These challenges have arisen by increasing healthcare demands across the world, exacerbated by an ageing population, increased lifespan and chronic conditions. To meet these needs, a ‘biopsychosocial’ shift from reactive to proactive health is necessary with a patient-centric emphasis (personalised, preventative, participatory and predictive) that includes ‘gender-specific medicine’. The management of the menopause, part of post-reproductive health, requires a life-course approach as it provides a framework for achieving a women’s preferred health outcome. Surveys from www.menopausematters.co.uk have consistently shown that women do not feel informed enough to make decisions regarding Hormone Replacement Therapy and alternative therapies. Health professionals must meet this challenge. The recently published National Institute for Health and Care Excellence guidance on the diagnosis and management of the menopause highlights the need for tailored information provision. The Internet underpinned by the academic disciplines of Health Web Science and Medicine 2.0 has potential to facilitate this shift to biopsychosocial medicine and tailored information within a life-course framework. The concept of Health Web Observatories and their potential benefit to a life-course approach using tools such as www.managemymenopause.co.uk is discussed.