It was first recorded by American country music singer Patty Loveless for her 1993 album, Only What I Feel and released in March 1994 as the fourth single.

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.

The universal power of the song became evident the first time she performed it - for an audience of crusty media types at a convention in New York.

"I saw this guy breaking up, sort of rubbing his eyes and trying to control his feelings, and I went up to him after the show and said, 'I didn't mean to make you cry'.

"[4] Jack Hurst from Chicago Tribune viewed it as "exceptional material" on the album, with "a highly affecting lyric about mileposts of life".

[5] Alanna Nash from Entertainment Weekly felt that the singer "reaches her artistic zenith on the soul-rattling ballads", remarking "the enormously involving" "How Can I Help You Say Goodbye".

[6] Hoelzle and Smith from the Gavin Report noted, "Patty was apparently so moved by this song that she had a hard time getting through it in the studio.

"[7] Jim Abbott from The Sentinel wrote, "By far the most emotional song on the album is "How Can I Help You Say Goodbye", a ballad about how leaving childhood friends, divorce and death affect the relationship between a mother and her daughter.

"[10] Chuck Campbell from Knoxville News Sentinel felt it should've been a hit, declaring it as "a bit melodramatic (about a dying mother), but delivered with simple grace by Branigan.