Hesitance is an innate human psychological phenomenon pervasive in our daily life. Although it is very complex and still not fully understood, there have been many studies related to this interesting topic. In this study, we proposed two fundamental problems about hesitance: the first is the generating problem, which is related to how to elicit hesitance information from human thinking; the second is the measuring problem, which is related to how to devise effective and reasonable methods to measure hesitance degrees from given hesitance information. With these two fundamental questions, we first discussed and analyzed several examples in real life involving hesitance, showing that it can indeed be recorded and represented. Then we roughly classified the hesitance information into two major classes: static hesitance and dynamic hesitance. Some simple and interesting methods were proposed to elicit hesitance, and more reasonable methods were proposed to measure the hesitance degree from the two classes of hesitance information. All methods that have been discussed in this study try to avoid complexity in every aspect while reserving strictness and reasonability; therefore, the present study provides suitable information for practitioners with different backgrounds.