A dilation of the pampiniform venous plexus in the scrotum above the testicle, called a varicocele, affects approximately 15% of the general male population. While the majority is asymptomatic, pain results in up to 10% of cases of varicoceles. The pain associated with varicoceles is typically mild and is described as heavy, achy, or dull—and is usually isolated to the testicle or spermatic cord. Guidelines clearly recommend varicocele repair in males with varicoceles, infertility, and an abnormal semen analysis. While chronic, severe pain is an additional indication for repair, a careful evaluation to rule out other etiologies in addition to a period of conservative management are necessary prior to surgical treatment because of the high incidental prevalence of varicoceles in the general population. Several techniques for varicocele repair have been described, including retroperitoneal, laparoscopic, inguinal, and subinguinal. Additionally, recent adjuncts to improve visualization and identification of critical structures including the operating microscope and microvascular Doppler ultrasound have improved success and complication rates. With careful patient selection, outcomes of varicocele repair with regard to pain are excellent, with over 90% of patients experiencing symptomatic relief. After failure of conservative treatments, a varicocele associated with pain should be considered for repair, and the microsurgical subinguinal approach is the gold standard surgical treatment, offering excellent outcomes while minimizing risk of complications.