Alexander the Great lived from 356 to 323 BC, passing away at the age of 33. He waged war as the commander of many battles at the young age of 16 years old and eventually conquered the entire known world from the mountains of northern Greece to the territories of northern India. Never losing a battle to any adversary (from soldiers in Greek city states to the warriors of kingdoms of northern Africa, including Persia and Asia Minor), Alexander was said to be the epitome of ancient history heroes, with one exception: his relationships with other adult males.

While relationships between established, grown men and young boys (around the age of 13 years old) were widely accepted among ancient society members, Alexander the Great stretched the generally accepted limits of male love. He had many relationships with young male escorts in addition to longer-lasting relationships with peers, including his lifelong love, Hephaestion.

Hephaestion and Alexander grew up as childhood friends and were both tutored by Aristotle, who embraced paederasty himself. The love fostered as childhood friends between Alexander and Hephaestion continued to grow as the two entered adulthood. At Hephaestion's death, Alexander is said to have laid upon his body for a day and a night and had to be dragged away. Alexander remained mute for another three days and ordered all cities under his control to mourn for Hephaestion.

Early on, Alexander's parents King Philip II and Olympias sensed his fondness for male companionship over the female version and brought Kallixeina to court to pleasure and serve Alexander. Kallixeina was a professional escort. However, Alexander was not completely swayed to give up his relationships with the male persuasion. Nevertheless, he did sire a child and marry more than once, despite his fondness for men.

Alexander received an eunuch from the Persian king Darius after the latter's defeat at the hands of Alexander. The eunuch's name was Bagoas, and he and Alexander forged a relationship that lasted well into Bagoas' adulthood. Curtius described Bagoas as "a eunuch exceptional in beauty and in the very flower of boyhood, with whom Darius was intimate and with whom Alexander would later be intimate." Eventually, Alexander installed Bagoas in a villa outside of Babylon and required that all of his officers and escorts render him honors. A relationship that began with only escort-like qualities grew into a full-blown love affair.

Alexander's troops respected and admired him as a great military leader. Despite generally negative attitudes toward adult male homosexuality, the men in Alexander's armies embraced his close relationship with Hephaestion and Bagoas (among other young men brought along as male escorts for Alexander). After a hard-fought victory, Alexander's troops encouraged Alexander to kiss Bagoas in a celebratory dancing contest. Plutarch wrote:

…they shouted out for him to kiss Bagoas, and never stopped clapping their hands and shouting till Alexander took him in his arms and kissed him warmly.

However, just as Alexander's troops openly accepted Alexander's relationships with men, there were many critics who refused to honor him or his lifestyle. The satrap Orsines refused to honor Bagoas and said, "I've come to honor the friends of Alexander, not his whores." Orsines' comments caused Alexander to condemn him to death. Additionally, the philosopher Diogenes berated Alexander for his sexual enslavement to Hephaestion.

Throughout history, many Greeks and other fans of Alexander the Great have resisted accepting the indicators that he may have lived a bisexual lifestyle, especially given the fact he is regaled as one of the greatest warriors of all times. Historians have consistently reported that Alexander the Great's life included at least two great male loves; Greek government officials still continue to do their best to quash these stories, attempting to save the honor of Alexander, despite Alexander's own openness about his love for other men.