Songfacts®:

• In this song, Hutchinson time travels to deliver a message to his younger self, letting him know that everything will be OK and alright. "I took the exercise of writing to my younger self really seriously and was really moved when I saw what thoughts came to the surface - forgiveness, acceptance, determination and hope," he said. "It was a healing experience to look back and realize how much I've grown up, and it was humbling to realize that all that advice to my younger self is also advice I'd give myself today."
• This is the opening track to Hutchinson's fourth album Easy Street, which like his first two albums (That Could've Gone Better, 2003 and ...Before I Sold Out, 2006) was self-produced and released on an independent label. Hutchinson says the track is "the closest I've ever come to getting a song exactly how I heard it in my head."
• In a Songfacts interview with Eric Hutchinson, he said of "Dear Me": "I wrote a bunch of angry songs and I took a step back and I said, You know what, I don't think this is really what I'm trying to take away from this experience. And how do I spin this into something positive in my life and how do I learn from this?
  
  I started thinking about my younger self, and I quickly started taking the idea of if I only had a few minutes to tell my younger self something, what would I say? I took the exercise pretty seriously and the song came together pretty quickly, I'd say."