My crush, my awkwardness, and the What-ifs that still haunt me

It was 2006 and the 12th board results had just come out. I had done really well and a few days later I was cycling to the market when I saw my crush. She and I had been classmates in coaching, and though we’d only spoken a few times before, I had a huge soft spot for her.

I gathered all my courage, said hi, and to my surprise she greeted me with the most genuine smile. We spoke for about 10 minutes — just casual stuff about studies and life. Then, out of nervousness, I blurted something silly about her board marks, pointing out that she hadn’t been completely honest about her earlier results. She just smiled, but the conversation ended soon after. That turned out to be our last real interaction.

Not long after, life changed drastically. I left town for college, she moved away too, and soon after we both faced personal tragedies. I lost my mom, she lost her dad. There was no way to reconnect, and life just carried us forward.

Years later, I tried finding her on Facebook and eventually did. She accepted my request but barely responded to my messages. I took the hint and stopped pushing. I moved on, dated other people, focused on my career. Still, she stayed somewhere in the back of my mind.

Last week, I came across someone with the same name at work, and it brought everything back. Out of curiosity, I looked her up and saw that she’s been married for years, happy with her life. And suddenly I was 17 again, replaying that one 10-minute conversation in my head — wondering if I messed up, if I ever had a chance, or if it was never meant to be.

Logically, I know she probably never thought twice about me. Still, almost two decades later, my brain keeps replaying that moment like I dropped the easiest catch of my life right at the boundary and lost the match. It’s such a small, silly memory, but it still stings