Songfacts®:

• Sometimes the hardest lessons to learn are the least complicated.
  
  Indigo Girls are Emily Saliers and Amy Ray. When it comes to songwriting, they contribute equally but write separately. Saliers wrote "Least Complicated." In a Songfacts interview with Saliers, she told the story: "I wrote that song actually sitting two stories above. I was in my house, I remember it very clearly, and I was looking down onto the street, and there was this boy and this girl, or young man and woman, I forget how old they were, exactly. But they were just holding hands and walking down the street. And I was going through some personal love crisis at the time - I can't even remember what it was - and I just started thinking, 'I don't want to be cynical at this young age,' but I looked down at them, and it looks so easy, and I was just like - 'You just wait.' Because what human beings do is repeat their patterns, oftentimes.
  
  I used a lot of the school metaphor, like buying a ring. I bought my seventh-grade boyfriend a ring, that's a true story. So the part about not being cool... like girls weren't supposed to buy boys rings, but that's what I did, and I just thought back to my school days. It's about lessons learned, that's where the image of the school days came in. And the fact that truly, if we could live our lives so much more simply in principle and not repeat the same mistakes, then we'd be happy. But it's so hard to do - at least for me."
• Saliers says that she gave her seventh-grade boyfriend the ring. "He was pretty gracious about it," she told Songfacts. "I think he was taken aback, actually. I bought it at Woolworth's. It was a really cheap, like, high-school-looking ring with a red fake stone. It was awful. I liked him so much, but that relationship didn't last past seventh grade, so it's okay."
• This was the only single from Swamp Ophelia, the duo's fifth album. Indigo Girls were never a singles band, with a fanbase that tended to buy their albums. Swamp Ophelia and its predecessor, Rites Of Passage, each sold over a million copies in the US. A few years later, Indigo Girls were a main stage act on the Lilith Fair.