There is increasing interest to work with user generated content in social media, especially textual posts over time. Currently there is no consistent way of segmenting user posts into timelines in a meaningful way that improves the quality and cost of manual annotation. Here we propose a set of methods for segmenting longitudinal user posts into timelines likely to contain interesting moments of change in a user’s behaviour, based on their online posting activity. We also propose a novel framework for evaluating timelines and show its applicability in the context of two different social media datasets. Finally, we present a discussion of the linguistic content of highly ranked timelines.