Background Vasectomy is a procedure that results in permanent yet reversible sterility and remains a great contraceptive option for many. Previous research studies have highlighted frequency of vasectomy utilization, defining characteristics of individuals who opt for this method, various surgical techniques, and the risks and benefits associated with the procedure. What remains to be defined is why or why not individuals may experience post-vasectomy regret and whether the previous characteristics correlate. Objective The objective of this review is to synthesize information regarding reasons individuals may regret their vasectomy and seek reversal, what options exist for accomplishing the reversal, and patients’ fertility prognosis post-vasovasostomy. Methods This review utilized a combination of secondary and tertiary data analysis across a wide scope of academic databases pertaining to the topic of interest. Results Typically, most males who have sought a vasectomy are satisfied with their decision, however, approximately 6% of this population seeks reversal. Key factors influencing vasectomy regret include age at the time of vasectomy, parental status, pre- and post-operative relationship status, unresolved physical and psychosexual problems, and development of chronic scrotal pain following the procedure. Few options exist for vasectomy reversal including microsurgical reconstructive vasectomy reversal (VR) and sperm extraction for in vitro fertilization. There is no guarantee that fertility will be restored in any case but a major predictive factor for success is the time interval prior to reversal. Conclusion Vasectomy is intended to be a permanent form of contraception; however, a minor chance remains that individuals may experience post-operative regret due to various factors. This warrants proper comprehensive counseling by the patient’s provider regarding benefits and risks, procedural outcomes, opportunities for reversal, and fertility prognosis.