I’ll Always Regret That You Weren’t My First Kiss


When I look back at my life, I have a staggering number of regrets. I have made so many massive mistakes. If I could go back in a time machine, I would change most of the major decisions I’ve made as an adult. And yet, my biggest regret is not something that I did, but something that I didn’t do. That’s the one that haunts me.

I regret that I never kissed my first boyfriend, the one I had when I was 12. I know it’s completely ridiculous that this is the one thing in my past that I would most like to fix. But I truly think that if he had been my first kiss, my life would have been different.

I loved him from the first day we met. We were eight years old at the time. What could an eight-year-old kid possibly know about loving someone? All I can say is that I knew immediately that he was the one.

He had the most beautiful green eyes I’ve ever seen. To this day, I love guys with green eyes simply because they remind me of him. For several years, he was the best friend I’ve ever had. Then when we were 12, I found out that he liked me. I was ecstatic. From then on, he was my boyfriend. We hung out at school, talked for hours on the phone at night, gazed lovingly into each other’s eyes while slow-dancing at the school dances. One night, while we were joking around on the phone, I told him I loved him. And he said it back. He even said he always thought that we would get married someday.

So why weren’t we making out all of the time? I was too terrified to make the first move. A first kiss is supposed to be special, and I wanted it to be perfect. I’m not really sure why he never tried to kiss me. My best guess is that because I was battling depression toward the end of our time together, he was too freaked out. The depression is what broke us up. It made me paranoid that he didn’t really care about me. One day, I very stupidly told him that I wanted to break up. I was desperately hoping that he would fight for me. He didn’t.

That was it. I lost my boyfriend and my best friend in one fell swoop. I tried to take it back. I called him and tried to restore some semblance of our friendship, but it was too late. He didn’t care anymore. The last time I saw him was at a reunion right before I graduated from high school. He was perfectly friendly, but his feelings for me had vanished. My feelings for him never did.

I dream about him all of the time. I dream that we run into each other somewhere, and we start talking, and eventually he kisses me. It’s everything I hoped it would be. Then I wake up and my heart breaks because I’ve lost him all over again.

My actual first kiss was with some random guy who I made out with simply because I was 14 and I wanted to kiss someone. It was the antithesis of special. None of the relationships I had following it were anything remarkable either.

I’m 33, and I’ve never been in love with anyone other than the green-eyed boy. The one I never kissed. Maybe if I had, we would have stayed together. Maybe we would have gotten married, just like he thought we would. Or maybe we still would have broken up. But at least I wouldn’t be tormented by the thought of the kiss I never had. At least I would have one less thing to regret.