Ejaculatory dysfunction, encompassing conditions such as premature ejaculation (PE), delayed ejaculation (DE), anejaculation, and retrograde ejaculation, significantly impacts male fertility, psychological well-being, and quality of life. This chapter provides a comprehensive evaluation of these dysfunctions, emphasizing the importance of creating a supportive environment for accurate assessment and effective management. The evaluation of PE involves a detailed medical and sexual history, physical examination, and the use of validated questionnaires such as the Premature Ejaculation Diagnostic Tool (PEDT) and Index of Premature Ejaculation (IPE). The chapter also explores the diagnosis of DE, highlighting the necessity of distinguishing between lifelong and acquired forms, and considering both clinical and psychosocial factors. Retrograde ejaculation and painful ejaculation are assessed through medical history, physical exams, and specific diagnostic tests, including post-ejaculatory urinalysis and semen analysis. Additionally, the evaluation of ejaculatory anhedonia involves an extensive history-taking process and a combination of physical and psychological examinations. This chapter underscores the importance of a thorough, multifaceted approach to diagnosing and managing ejaculatory dysfunctions to enhance patient outcomes and quality of life.