- "One Promise Too Late", in which the singer meets her soul mate but decides to stay with the husband who's never been less than good to her.
- Also, her "The Greatest Man I Never Knew" — mourning the singer's late father.
- "Somebody's Chelsea" is about the singer meeting an old man on the plane home who tells her about his recently deceased wife and how absolutely he loved her. The title remarks that "every woman wants to be somebody's Chelsea."
- "What Do You Say" starts out on a fairly whimsical note, slipping into "sad" for the second, and then the last one...get your Kleenex ready, folks.
- "She Thinks His Name Was John" is another one that'll rip your heart out and stomp on it. A woman has a drunken one-night stand and finds out he was HIV-Positive, which then turns into full-blown AIDS for her. And this was made at a time when the prevailing belief was that "good people" didn't get AIDS. Worse: During their encounter, she apparently was so drunk that she (later) literally could not remember anything about him, except for several vague details (broad shoulders, blue eyes and black hair) and that his name was John; she doesn't even think to get DNA testing that might help them find this man. In the end, the woman is on her deathbed, knowing she will never get married or have children and that her life was destroyed by one drunken night of stupid choices.
- The entire album For My Broken Heart, recorded to help Reba work through her grief after her road band was killed in a plane crash.
- Her duet with Kelly Clarkson, "Because of You" has been known to break hearts.
- "Fancy" is the story of an eighteen-year-old girl whose father has abandoned her, her infant sibling, and her mother who is too ill to support any of them. Fancy's mother decides that the only way Fancy can get out of that life is if she uses her sexuality and basically become a prostitute. Not only that, but there is no mention of what happens to Fancy's younger sibling other than they got taken away by "the welfare people" and it's unlikely Fancy ever saw them again.
- "Every Other Weekend," a duet with Kenny Chesney is sad enough by itself, about a divorced couple who only have contact with each other when they exchange children. They both regret their divorce and are still in love with each other, but say nothing because they think the other is "over it." The video, however, turns it into Tear Jerker territory. For fans of the Reba television show, Joanna Garcia and Steve Howey (Cheyenne and Van) play the male and female narrators. The video also stretches the story over a period of about ten years, with the children aging from elementary age to teenagers while their parents continue to love each other from afar. The line "For fifteen minutes, we're a family again" is especially heartwrenching.
Tear Jerker / Reba McEntire