Of all my mishaps, this is the one that bothers me most. It was #1 in my Top 5 Biggest Mishaps (read that HERE). This one is so huge for me because for three years I worked towards getting my moment with Dream Girl…and when I finally did, I blew it big time.
10th grade was when the kids in my town entered high school for the first time, and I saw her within minutes of walking through the door. Everyone was gathering in the cafeteria, and my eyes were immediately drawn to her. She floated around the other side of the room like a fairy princess. Many years have passed, but I will have this moment etched in my brain forever.
Dream Girl stood about 5’2″ with beautiful blonde hair. That first day, she wore tight blue jeans and a light blue button down shirt. The buttons on her shirt looked like they were struggling to contain her breasts. She seemed to be so happy, and bounced around from person to person, friendly with them all. I was mesmerized. I was infatuated. I was instantly in love.
If you’ve seen Can’t Hardly Wait, or I Love You, Beth Cooper, then you know exactly who this girl was to me. But unlike in those movies, I didn’t turn down other opportunities because of my love for her. That being said, every moment of my high school career seemed to lead up to my one big chance, which would come only months before graduation.
Early in my senior year, I spotted an opportunity to get to know her. She was a library aid during her study hall, so I (the smart man I was) signed up to work with her. Three days a week it was just her and I. Like a dream come true.
Even though Dream Girl was in the popular crowd and I wasn’t, she never made me feel that way. She was so nice, and we became friends. I asked her out early on in the school year and she turned me down, but she never made me uncomfortable about it. Our friendship continued to grow throughout the year.
In March, my opportunity would finally come. Our school was hosting an event and she asked me to help her work it. After agreeing, she suggested that the two of us should go out to lunch together after it was over. While not an “official” date, it was more than enough to get me excited.
I arrived to the event early in the morning and she was already there. She wore a tight white dress that was very short. It may have been one of the sexiest things I ever saw her in. Three of us went out to pick up pizzas for lunch. She sat in the back seat of my Jeep Wrangler and when we arrived, I helped her out. She spread her legs, revealing the lacy white panties she wore. I’m 99% sure my eyes popped out of my head like in a cartoon. I couldn’t look away at this delightful sight. When I finally did, I looked up into her eyes and she was staring at me, smiling.
Over lunch, I overheard her talking to her friend. It sounded like they were making plans for after the event and I was crushed! How could she forget about our plans? I spent the rest of the day completely bummed out, and as soon as the event was over, I bolted in shame. On Monday, back in school, she greeted me really upset. She asked what happened to me, and told me I blew my chance. Yes, we’ve all seen it a hundred times in the movies. That moment where one character does something drastic because the misheard something another character said. If you ever wondered if this actually happens in real life, apparently it does to me!
It’s completely unhealthy to do this, but I have often wondered what would’ve happened if that lunch happened. The whole scene helping her out of my Jeep leads me to believe that really good things would’ve happened. I do feel that it was an honest mistake and maybe she was a bit harsh on me, but that’s from my perspective. I have no idea how me not showing up for her that day made her feel. That being said, this was instantly one of my biggest life regrets, and one that will never be topped. I put in so much time with this girl, only to flub it at the end, never to get my chance again.