"Sylvia's Mother" is autobiographical, with songwriter Shel Silverstein drawing upon his unsuccessful attempt to revive a failed relationship. Silverstein had been in love with a woman named Sylvia Pandolfi, but she would later be engaged to another man. Desperate to continue the relationship, Silverstein called Pandolfi's mother, Louisa, but she instead told him that the love had ended.
The lyrics tell the story in much the same way: A young man, despondent and near tears after learning that his ex-girlfriend (Sylvia Avery, with whom he had an earlier bad breakup) is leaving town, tries to telephone her to say one last good-bye, or at least try to get a suitable explanation as to why their relationship failed and maybe try to rekindle things. However, Sylvia's mother (Mrs. Avery) tells him that Sylvia is engaged to be married, and is trying to start a new life in Galveston. She asks the man not to say anything to her because she might start crying and want to stay.