In the three verses, the narrator describes with florid imagery three experiences of loss in her life: moving away from her best friend as a young girl, separating from her husband as an adult, and her mother's death. Each time, in the repeating chorus, her mother seeks to comfort her, asking "how can I help you to say goodbye?"
Loveless' album, "Only What I Feel" had sold over 650,000 copies and had been certified as an RIAA Gold Album. Sony/Epic was receiving requests from radio stations that this song be released as a single, and in March 1994 it was released. This song climbed up the charts, reaching #3 in June. It was also nominated for the 1995 Grammy Awards for Best Female Country Vocal Performance and Best Country Song. The accompanying video was also nominated by both the CMA and the ACM as 1995 Video Of The Year.
Burton Collins, who was an actor at the time, had never written a song before "How Can I Help You Say Goodbye". He told Country Weekly that the title was spoken to him by his grandmother shortly before her death in 1988. After being introduced to Karen Taylor-Good by a mutual friend, he wrote the song with her. Collins said that he and Taylor-Good wrote the song in three hours.