Meaning of "Chester The Molester" by Sloan

"Chester the Molester" is a satirical commentary on a manipulative and disingenuous person who tries to deceive others for his own gain. The lyrics depict Chester as a character who uses his charm to manipulate women into thinking he is single, all the while being deceitful and not keeping his word. The repeated reference to a ring he is trying to hide symbolizes the lies and deception he uses to lure women into his trap. The song highlights the consequences of his actions, as ultimately, he loses what he was trying to gain. This can be seen as a cautionary tale about the pitfalls of manipulation and deceit, pointing out that it eventually leads to loss and disillusionment.