Insight is a salient psychotherapeutic progress but has rarely been measured in a controlled experimental setting. This study aimed to assess whether textual micro-counseling dialogue could validly evoke insight and to explore the characteristics of insight. The guessing riddle of cognitive psychology was used as a reference of the experimental paradigm. Specifically, textual micro-counseling dialogues applying cognitive restructuring techniques were presented. The participant first read a description of a psychological distress (“problem”) and then an explanation (“solution”). Zero-, low-, and high-restructuring solutions were randomly matched to the problems and it was expected that they would trigger different levels of insight experiences. Experts and students evaluated the adaptability and emotional valence of problems, and the insightfulness, novelty, adaptability, and emotional valence of solutions. For both experts and students, different intensities of insightfulness were produced across high-, low- and zero-restructuring solutions. Novelty significantly discriminated the high-restructuring solutions from the other two solution types. Adaptability and emotional valence could discriminate the high- and low-restructuring solutions types from the zero-restructuring solution. Insightfulness had high correlations with novelty and adaptability. These results indicated that textual micro-counseling dialogues with a high-restructuring solution could validly produce the greatest insightfulness and the features of high-restructuring solutions may have reference meaning for improving psychotherapeutic effect.