Handwriting is an art form that most people learn at an early age. Each person's writing style is unique with small changes as we grow older and as our mood changes. Here we analyse handwritten text in a culturally significant personal diary. We compare changes in handwriting and relate this to the sentiment of the written material and to the topic of diary entries. We identify handwritten text from digitised images and generate a canonical form for words using shape matching to compare how the same handwritten word appears over a period of time. For determining the sentiment of diary entries, we use the Hedonometer, a dictionary-based approach to scoring sentiment. We apply these techniques to the historical diary entries of Rosamond Jacob (1888-1960), an Irish writer and political activist whose daily diary entries report on the major events in Ireland during the first half of the last century.