Earl being a bit older, had a thing going now and again with the pogo-stick-kid's Mom. Makes sense.
As to why he was always trying to hook up his buddy with nice women, I think he was trying to help the poor kid who was sort of confused sexually. He likes girls, even has a dream girl in mind, however, he wears a really GAY belt buckle. The heart buckle is a GIRLS rodeo buckle. NO manly cowboy would EVER wear one. Never! So ..
OH, and even a manly thing like having a schedule so you never have to do anything "right now", that is alien to the kid, but second nature to Earl. Manly vs gay.
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