The Mid Life Dating Files 2025

Is there an age or year of your life you would re-live?

If I could relive any time in my life, it would be my 8th or 9th grade years—1986 and 1987. Those were, without a doubt, some of the best years of my life. Everything just felt lighter then—life was simple, fun, and full of possibility. I was dating the best guy ever, the one who still crosses my mind after all these years. He was the one who got away.

If I could go back and do it all again, I would have held on tighter and never let him go. I truly believe my life would’ve been even brighter if we had stayed together. He was, and still is, one of the kindest, most genuine souls I’ve ever known. Sweet, smart, funny, and so easy to be around—he had this way of making everyone feel special. He was handsome, popular, athletic—your classic all-American boy—and everyone loved him. But beyond all that, it was his heart that made him unforgettable.

When we were together, we laughed endlessly and found joy in even the simplest moments. I can still remember the way he’d look at me and make me feel like I was the only girl in the world. I don’t even know why we didn’t stay together—maybe life just got in the way, or we were too young to understand how rare that kind of connection was. But if I had the chance today to go back and be with him again, I wouldn’t hesitate for a second.

They say, “you don’t know what you’ve got till it’s gone,” and I’ve learned just how true that really is. Some people leave a mark on your heart that time can’t erase—and he’ll always be that person for me.