This study aimed to investigate how individuals regulate emotional expression in different crying situations. Using a questionnaire survey, we examined the everyday crying experiences of 173 Japanese university students, focusing on how empathy and personality traits influence the decision to cry alone or in presence of others. Statistical analyses revealed that individuals with higher agreeableness scores tend to suppress crying in presence of others when experiencing emotions triggered by a close person's sadness or by fictional and documentary characters. However, in situations involving achievements or defeats, they are more likely to share their emotions by crying with others. These findings suggest that highly agreeable individuals are particularly sensitive to social norms and adjust their emotional expressions to align with contextual appropriateness. This study highlights the role of personality in emotional regulation and provides insight into the social functions of crying in interpersonal contexts.