If I could relive one day from my past, I think I’d choose New Year’s Eve 1988.
Not because it was a particularly happy day.
I had flown back to Jacksonville after spending Christmas with Mom and the rest of the family. She had already made plans to fly to Texas to visit my grandmother, who lived in Carthage, only about an hour away from me. I had my own plans. I was supposed to spend New Year’s with my girlfriend.
Then the relationship fell apart.
Suddenly, the holiday I had imagined was gone, and I was miserable. I called Mom, and she told me to come to Carthage.
So I did.
I spent that weekend being nursed back to emotional health by my mother and my grandmother, two of my favorite people in the world. At the time, I’m sure I was mostly focused on the breakup. I was young, hurting and probably thinking far more about what I had lost than about what I still had sitting right in front of me.
That’s what makes the idea of going back so appealing now.
I wouldn’t go back to change anything. I wouldn’t try to save the relationship or warn my younger self about what was coming. I wouldn’t even want the pain erased, because the pain was what took me to Carthage in the first place.
I’d just want to be there again.
I’d want to hear Mom’s voice. I’d want to hear Grandma’s voice. I’d want to sit in the same room with both of them and watch them talk and laugh and fuss over me. I’d want to let them take care of me while knowing, this time, just how extraordinary that ordinary weekend really was.
There’s a strange irony in choosing New Year’s Eve. We usually spend that night looking forward, thinking about what the next year might bring. In 1988, I was looking forward and seeing disappointment. The future wasn’t unfolding the way I wanted it to. Nearly four decades later, when I look back at that weekend, the breakup barely matters.
What matters is that Mom said, “Come,” and I went. What matters is that for a little while, my mother and grandmother were together in the same place, and I was there with them.
There’s a song built around the idea of being granted one more day with someone you’ve lost. I understand that longing more now than I ever could have then. But I also understand the flaw in the wish.
One more day would never be enough.
If I were somehow given December 31, 1988, again, I’d know from the moment I woke up that the clock was running. Every conversation would matter more. Every laugh would sound different. I’d notice things I probably ignored the first time. And as midnight approached, the gift would start to hurt because I’d know I was about to lose that day all over again.
Still, I’d take it. Not because I want to live in the past. I don’t. But because getting my mother and grandmother back together in the same space and time, even for one ordinary day when I happened to be heartbroken, would be priceless beyond priceless.
And maybe that’s the real lesson hidden in the question.
We don’t always know which days will become precious while we’re living them.
Sometimes the day we can’t wait to get through becomes the day we’d give almost anything to have back.
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Copyright © 2026 Doug DeBolt