We've all hooked up with, or dated that person. You know, that person who, when you look back on your life, you think to yourself, what the hell was I thinking! Unfortunately, for me, I've had one too many of those. My first What Was I Thinking! began back in high school. I had the biggest crush on this guy. Let's call him S.

Believe it or not, back then, I was unbelievably shy. I was so shy, that I could barely even talk to S. And whenever I would talk to him, it was the most awkward conversation imaginable. I guess I just never knew what to say to him, and just blurted out whatever came to mind. Sometimes I said things to him like, "Why are you wearing sunglasses?" on a sunny day. Or, "Why are you wearing a belt?" One time, I even pulled a Clueless and sent myself flowers on Valentines day just to get his attention, because I didn't know what to say to him that day. And of course, he didn't even notice.
But it wasn't until June 1999 that it happened. I asked S to my senior prom. I finally worked up the courage to actually ask him. Alright, fine. I asked online. But whatever, I still asked him! After what felt like five minutes to finally answer the question, he said "When is it?" I told him. "I don't know. I think I'm going on vacation that day. Sorry," he said. Ouch!
The next day at school felt like an episode of Gossip Girl. Everybody knew that I asked him to the prom, and that he said no. People were whispering as I walked down the hall. People were staring at me. Or, at least, that's what it felt like to me. But then a very good friend of his told me that he was indeed going on vacation. That made me feel some what better about myself. But I was still disappointed. My ex boyfriend had also asked me to the prom, but I turned him down with hopes of bringing S. And obviously, by the time he turned me down, my ex already had a date.
Cut to - prom night. I ended up taking my best guy friend and had a blast. Screw S. I didn't need him. I had a better time than I ever would have had with him anyway. It probably would have been nothing but awkward conversations and wondering if he was going to kiss me all night long.
The very next day after the prom, I was driving down the boulevard with my girlfriend and she spotted him. Wait a minute, I thought he was on vacation! A-ha! He did lie. I knew it! And for that moment, that shy girl suddenly disappeared as I drove by and rolled down the window. He was with a group of his friends, and I know that they all saw me drive by. I pulled over and asked "So, how was your vacation?" What did S do? He hid behind the telephone pole. Um, seriously? Because that'll really hide a person?
After high school, I was totally over S. He was a jerk in my book, and all of my friends hated him for what he did to me. It was just an ordinary day in college, and that was when I saw S. What!? He doesn't go here. What the hell is he doing here? Well, apparently he transferred schools. To my school. No, it's not the Felicity-esque fairy tale ending you'd hope for... he just thought it was a good school.

But oddly enough, we actually became friends. Which was party due to the fact that he was close friends with my then-boyfriend. Awkward! So, unfortunately, I was forced to hang out with him all the time. Eventually, when my ex and I broke up, me and S started hanging out a lot. Back then, a close friend of mine was trying desperately to get us together because she knew that my odd obsession was back. But due to an unfortunate turn of events, this friend was actually into him as well. Which I didn't even know about until recently! The first time around, things didn't work out with S. I guess it was just one of those things that wasn't meant to be. And never in my life did I see such terrible timing, year after year, after year! So, I gave up. But things didn't end there.

After I realized what this so-called friend of mine was up to, I filled S in on the rest. And what do you know, me and S finally got together. I know, so very 90210 of us. It only lasted a short time. But for that time, I was the happiest girl in the world. After crushing so hard on someone for so long, I can't even tell you how good it felt to finally be together.
But everything must come to an end. Things ended poorly with S. Eventually, he chose the other girl over me. And I finally called it quits with S. For a couple of years after college, I actually didn't see him for quite some time. But on one rainy day in New York City, I was at a happy hour and bumped into some old high school friends, and there he was! Of course, we didn't speak. But I still got a kick out of bumping into him. Because, well I don't know about you, but I just love bumping into ex's and showing off that everything is just grand. It drives the boys wild!













