Homestar was raised by his father and was encouraged to become involved with sports at a young age. He turned out to be a natural. However, he had a brain the size of a jelly bean. This was a problem if he ever wanted to get anywhere in school. After the ten step footrace, at which time he was eight, Strong Bad and Homestar became the best of friends. However, their gym teacher placed them in a boxing match against eachother. Strong Bad's weakness was athletics, so he lost by a long shot, and felt humiliated. Ever since then, he's been trying to beat Homestar in some kind of athletic competition. When Homestar was sixteen, his father said, "You need a girlfriend."
Homestar replied, "But I don't know any girls." His father said, "Well then, just pick up the first one you see." Homestar took these words literally, and when he was riding in his best friend Pom Pom's car one day, he saw a hitch-hiking hippie, grabbed her, and became her boyfriend.