confessions of a cruel SOB

This week I got together with a bunch of old friends from high school to have some food and drinks. After catching up on our current lives, we all started to reminisce After talking about girls we used to date, legendary parties and all the stupid dangerous shit we used to do riding our BMX bikes we turned to the wonderful topic of people we used to torment. Leading us all to the realization that we were a bunch of cruel bastards, and let me tell you once we accepted that the laughs really started, so I guess not much has changed.

Anyway this got me thinking about all the horrible shit I used to do to people for shits and giggles, so here are the top 5 cruelest things I’ve ever done to anyone. Names have been omitted to protect the innocent.

5. Pulled up a girls dress in the middle of the cafeteria – I don’t know how it was in your high school but in good old Hendrick Hudson High School the second you start your freshman year every girl you dated for the past 3 years of junior high left you to date upper classmen who had cars and a semi-stache. After two years of toiling away without ladies our time had finally come. A new batch of freshman arrived, we had cars, and hair in our pits. One young lady who will remain nameless, caught my eyes and like most young men who had zero game, I made picked on her constantly. At lunch one day she was walking by and I thought it would be a good idea to pull up her skirt, normally this wouldn’t be that big of a deal but she had a tight lycra skirt on which ended up getting stuck around her waist, embarrassed she ran into a classroom across from the cafeteria that happened to be holding a study hall for upper classmen. While I was a hero amongst my peers I always felt terrible for that one.

4. Threw gum into a girls hair for no reason – It was probably in sixth or seventh grade. My parents moved us upstate to northern Westchester County when we were little because they felt it was better than raising us in Yonkers. We didn’t have a ton of money so we lived in the apartments in the good zip code which was filled with young couples, suburban drug dealers, recent divorcees and families like mine looking for something better for their kids. Well, I befriended a girl who lived in the next building, scratch that I wouldn’t say she was my friend rather someone I would alternately be friendly with and torment. Unfortunately for her she was a fat girl with low self esteem so she would accept such treatment because she didn’t have a lot of friends. Anyway one day we were walking home after school and I had a mouthful of Bazooka, and I don’t know why but I just decided to spit it into her hair. She immediately grabbed it and within seconds it was completely tangled in her hair. She rain home crying. Later that day I went over to apologize and her mom laid into me about how bad of a friend I was, and she was right, I was an asshole for that one.

3. Broke up with a girl on a bet – This one was also one of my stupidest moments ever. She was the first girl I ever really had a crush and I was lucky enough to date her. We were young, maybe sixth grade. A lot of my friends were dating the fast girls your mother used to warn you about. Unfortunately for me this girl, although gorgeous for a sixth grader, was slow. We went on a date to Rolls, the local roller rink and popular make out spot and we didn’t make out. I was annoyed. I told my friend Steve Bell I was thinking about breaking up with her because we didn’t make out. He started making fun of me and bet me $5 that I wouldn’t break it off with her. So with my ego all hurt I marched across the cafeteria and told her 'it’s over' and walked away. She ended up going on to be the best looking girl in our graduating class. Good Job me.

2. Broke a dudes arm – It was during a sporting event so it wasn’t necessarily cruel but I needed to include something that wasn’t done to a woman so I don’t come across like some sort of misogynist pig.

1. Bedded down a girl I couldn’t stand just because her very nature pissed me off – This one, while probably not the cruelest, ranks first because I did it as an adult and it was the last time I was overtly cruel to someone. Before becoming the fourth most famous rapper on Philaflava I used to sell advertising. I was working at a company as an assistant account executive, and I sat across from this girl who while kind of cute was horribly annoying and shallow. I also realized that she had a crush on me. At the time I was already sleeping with the receptionist at this job. Who I learned after the first time I had sex with her and saw the tattoo on her leg of a teddy bear that said snuggles, was a stripper and not the good kind of stripper. No, no, no, she was the kind of stripper that worked bachelor parties. Anyway I got a new job, gave my two week notice and decided to kick it to this woman I hated with every fiber of my being. She ended up not really being a bad person she was just annoying and I was an asshole. Anyway after work one day I went shopping for a new jacket and asked her to come with me. Afterwards I walked her to the train and gave her a kiss goodnight. I knew I had her. One thing lead to another within a few days we are sleeping together. I let this go on for a few weeks and she started falling for me. Once I knew I had her where I wanted her I sent her an email telling her that she shouldn’t call me anymore. When she asked why I replied and said ‘because you are annoying as fuck’.

It ended up being a turning point for me, I eventually realized how mean spirited that was and decided to change my ways. As a payback I fell super hard for the next three girls I dated and they all broke up with me leaving me shattered. Good fun.