Letters To Grandma, To Me, To Yesterday and Tomorrow
- stephaniewilson
- Oct 3, 2023
- 4 min read

I set the plastic storage container on the table. It was big enough for one pair of shoes — an awfully small space to hold what would blow me over like a flimsy roof in a pitiless storm. But I didn’t know that yet.
I opened the lid and grabbed the top letter. The paper was aging, thirty years old now, and the handwriting looked archaic like a piece of history from an earlier iteration of human. Years ago, when I’d peeked into this bin of letters — maybe only ten years now — that handwriting seemed normal. But today it looked old-fashioned. Nobody writes with their hand anymore.
My mission was to unearth my grandmother’s long pen pal relationship with me from the boxful of letters I’d saved from various people. My letters to her were returned to me after she died. There were over fifty of them written from when I was in eighth grade to when I became a mom. Now, eighteen years later, I had the guts to read them.
As I sorted through, I recalled those pen pal days. I recalled the silliness my grandmother and I had together on the page from one mailbox to another. I recalled being tickled with whatever shenanigans I invented on the paper hoping to tickle her even more when she’d stand in her kitchen 3000 miles away reading it.
However, as I started to read through my letters, my memory of that pen-pal relationship wasn’t bearing out. There were shenanigans, to be sure, but only from my end. Where were Grandma’s funny letters to me? All I had was short communication from her. Did I not save her funny letters? Or were her funny letters in my memory an illusion? Had I invented her humorous replies to justify the things I wrote to her? Or was it wishful thinking?
Even odder, and more unsettling, was the person who wrote to Grandma in my name. She reminded me of myself in small ways, but otherwise, she was a stranger, and maybe not one I’d seek out for conversation. She wrote things to my grandmother I can’t imagine writing now — using jokes I’d never use with a grandparent. The best I can figure, she was pushing the envelope to be funny and trying to share adult thoughts with an adult. She was risky in ways I could never be. I sat there stunned that this alternate-universe me had been me.
I walked around in a funk over this for days.
This adolescent version of me was exactly as I’ve been learning she would be — a young person with an executive function yet to be developed. If you’d taken my recent diagnosis of ADHD into account as you read this risk-taking author, you’d have not gone into a funk. You would have understood. But I opted to drop off the cliff of self-cringe and drift offshore into a sea battle over who I used to be. Not fun.
In the letters written through the 1980s, I alluded to challenges I was weathering at the time, but I always seemed to brush a glittery stroke over things, promising my grandmother that life was rosy. Perhaps I wanted her to think I was fine. Maybe I wanted someone — anyone — to think I was fine. No doubt I wanted to believe I was fine.
But I’ll never know what I thought. Memory is not our reliable friend. Maybe an unreliable friend is better than an unreliable enemy. It depends.
At this point, I can only shrug.
I often wave away those years of my life as not completely, legitimately part of my actual life because they demarcate a person who is not completely me as I know her today. It’s as if I think of my life as two conflicting entities. One is a collection of various versions of me over time. The other is my most refined philosophical understanding to date — my true self, if that’s a thing. And while a true self is up for debate, there are certainly long-lasting threads.
For example, my letters to my grandmother often insist on being funny. Many of them have hand-drawn cartoon images to illustrate, which was a complete surprise to me. I’d always had this vague knowledge that I used to combine words and drawings, but I never had access to the actual data. I knew when I gave myself permission to draw cartoons for my stories today that there was precedence, but from where I didn’t know. In these ways, I haven’t changed. It’s a big surprise to discover tangible evidence of something you intuit but don’t know why.
The earliest letter I have from my grandmother’s stash was written in June 1979 to my grandparents when I was 14 years old, about to enter high school the coming Fall.
“I’m sort of glad to be rid of grade school and am looking forward to high school, but I’ll miss Middle School. And I won’t forget when I was little enough to swing on the monkey bars in the playground and was able to not touch the ground. But, of course, I’m not all grown up yet either. I still have a few years ahead of me. I can’t wait till I’m a grandparent and I’ll be able to sit back and read a thank-you letter from my grandchild. I mean, aren’t you just having the time of your lives reading this??!! (If you are, I suggest you see a doctor!)”
Silly girl.
Maybe I’ll write to that fourteen-year-old since now we’ve been introduced and we’re both letter writers.
Dear Whoever You Are,
I envy you that you can remember the monkey bars and can write to your grandparents. I have no memory of the playground and no grandparents. I wanted to let you know that in the coming years, it’s going to get harder before it gets easier. Over time you’ll learn to reframe the past. Sometimes the past is just another word for your opinion of yourself.
Trust me, you will rise and things will turn out okay. In fact, better than okay. One day it turns out beautifully. Hang in there. Don’t stop with the jokes. They’ll carry you through.
Love, Whoever I Am
I think I’ll write to her again in ten or twenty years. Or I hope so. We’ll see.
Happy Fall, dear ones.





Comments