Sorry, I have literally 0 knowledge on the issue but I saw on Wikipedia that Pol Pot was a fan of a broadcast called "Voice of America", and knowing he was quite the despotic dictator I was wondering, was he another one of America's numerous questionable allies? And does anyone know why America would condone an allied relationship with him? (Assuming they knew what he was doing, because if they did not then I would understand)
Unlikely, they generally sided with dictators only when they were anti communist.
Pol Pot was a chinese ally, and a fanatical communist.
The United States originally oppossed the Khamer Rouge takeover of Cambodia and order bombings on the country to that effect. However, the US would later provide non-combat support to the Khmer Rouge, and by extension Pol Pot, following the successful invasion of Cambodia by Vietnam.
This was done in an attempt to check the power of the Soviet-backed Vietnamese, especially following the Vietnam War. The Khmer Rouge were backed by China, who were viewed as the more agreeable influence out of the two communist powers.