For me, Valentine’s Day seems to bring out my regrets every year

When I was in elementary school, everybody in a class exchanged Valentine’s Day cards at school. Is it still that way? We each decorated a shoebox with our name on it. We cut a slit in the top for others to drop cards through. The displays were up for several days — and everybody was required to give a card to everybody else.

When I was in the fifth grade, I had a crush on a beautiful blue-eyed blonde girl named Wendy. She was my ideal girl when I was about 11 years old. I was terrified of anybody realizing this, though, because then she might know — and that seemed scary. I guess it was “puppy love” rejection I feared.

Since classes routinely gave cards to everyone, there were large packs of small, cheap cards that stores sold. I bought a pack of those generic cards — but I also bought one very special card, much nicer than the others, just for Wendy.

Surely, I thought, nobody will notice. Nobody will figure it out. My secret would be safe.

But little girls who compared the cards they received in our class did notice. And they talked among themselves. Before I knew it, everybody was whispering that I “liked Wendy.”

A couple of days later, I was alone outside of Golden Springs Elementary School. The school day was over, but I was still there. Almost everybody else was gone. But then I noticed Wendy walking toward me. She was still here — and now I had to talk to her.

“David,” she started very shyly, “do you like me?”

I was filled with panic. If I admitted the truth, she might very well tell me that she didn’t “like” me. She might tell me she had her eyes on some other boy. I didn’t know what might happen, but I feared the worst.

I don’t remember exactly what I said, but I lied. I denied everything. I said as little as I possibly could — and then I took off quickly. I was escaping my possible rejection. But as I left, I looked at Wendy’s face. She looked stricken. And she looked hurt. All I cared about was running away, but I saw that my denial hurt her young heart.

She made several more very obvious attempts to be friendly with me before we moved away, but I always found a reason to run. Other kids in our class continued to tease me about “liking” Wendy and I continued to deny it.

For several years after that Valentine’s Day, I felt regret about what had happened. After I got far enough away from my fears to see what had really happened, I realized that Wendy wasn’t coming to torture me with rejection. She was probably flattered. Maybe she “liked” me in return.

That regret stayed with me for years, because if there’s one thing I do exceptionally well, it’s to obstinately remain devoted to loves which have left me behind. Wendy was my first real regret when it came to love, even though we were only 11 years old.

The regrets I carry with me today are far more recent. They’re far more adult in nature. But my regrets about love all seem to be informed by the same fear of rejection which caused me to act like a little fool in the fifth grade.

My strongest regret about love today is a decision I made about how to handle something with a woman more than a decade ago. How long? I don’t recall exactly. Was it 12 years ago? 13?

I tell myself today that if I had handled that situation differently, my life would be totally different today. I tell myself that I would be happier. I imagine that I would have love and a family now if I’d handled things differently.

I know this regret is ridiculous. I’m well aware of the fact that if I’d made a different decision, I might have found a different sort of misery instead. The path we didn’t take — for each regret — could be far worse than the delight we imagine we would have found. We can never know for sure.

I know all that, but I still feel regret. I still put myself back into a specific moment and say, “What if I had simply…?”

Young Wendy was my first experience with botching love, but it wouldn’t be my last. As I sit here thinking about all the ways that I’ve managed to lose the love that some women would have liked to give me, I’m still naive and foolish enough to believe I’ll get one more chance at it.

And I’m still crazy enough to believe the time is coming — very soon — when I’ll finally get it right. And then maybe all my regrets about love can be left in the past.