This book constitutes the refereed proceedings of the 14th IFIP TC 9 International Conference on Human Choice and Computers, HCC14 2020, which was supposed take place in Tokyo, Japan, in September 2020, but the conference was cancelled due to the COVID-19 crisis.The 31 revised full papers presented were carefully reviewed and selected from 55 submissions. The papers deal with the constantly evolving intimate relationship between humans and technology. They are organized in the following sections: ethical and legal considerations in a data-driven society; the data-driven society; peace and war; our digital lives; individuals in data-driven society; and gender, diversity and ICT.