To realize a hyperconnected smart society with high productivity, advances in flexible sensing technology are highly needed. Nowadays, flexible sensing technology has witnessed improvements in both the hardware performances of sensor devices and the data processing capabilities of the device’s software. Significant research efforts have been devoted to improving materials, sensing mechanism, and configurations of flexible sensing systems in a quest to fulfill the requirements of future technology. Meanwhile, advanced data analysis methods are being developed to extract useful information from increasingly complicated data collected by a single sensor or network of sensors. Machine learning (ML) as an important branch of artificial intelligence can efficiently handle such complex data, which can be multi-dimensional and multi-faceted, thus providing a powerful tool for easy interpretation of sensing data. In this review, the fundamental working mechanisms and common types of flexible mechanical sensors are firstly presented. Then how ML-assisted data interpretation improves the applications of flexible mechanical sensors and other closely-related sensors in various areas is elaborated, which includes health monitoring, human–machine interfaces, object/surface recognition, pressure prediction, and human posture/motion identification. Finally, the advantages, challenges, and future perspectives associated with the fusion of flexible mechanical sensing technology and ML algorithms are discussed. These will give significant insights to enable the advancement of next-generation artificial flexible mechanical sensing.