From girls to women and me becoming a man from a boy, my love life truly was, and still is a spectacle. From middle school throughout high school I’ve had girlfriends, crushes, and even gotten stood-up… on multiple occasions. One of my strangest moments was playing strip poker with a girl from high school whom I rarely talked to until only recently after we graduated. Not exactly sure how we got to that situation, but it was definitely interesting. I got to hold hands with my first crush roller skating to Aerosmith’s’ “I don’t want to miss a thing.” Only she was skating backwards, not messing with my masculinity whatsoever. With all of that being said, here’s a much longer story of how my love life has gone.
The Girls From School
Everyone seems to have those typical cliché high school romantic life. You’re either all alone, hooking up with multiple girls, or have that long lasting relationship with your sweetheart. So where am I in this category…? When I was in school, I was normally a very quiet person. Stuck to myself for the most part, and didn’t have many friends. I knew a lot of people, but that was mostly it. I did have a small circle of friends I’m proud to say that are close to me to this day. My grades could have been better, but I found it difficult to pay attention in class because I was distracted easily by the girls. They always thought I was cute, like Snoopy(sorry, had to use that Rush Hour reference).
My freshman year was quite a wild one. Never thought I would be brave enough to ask out as many girls as I did. I had the biggest crush on this girl that seemed really interested in my life, Erica. We never dated or anything, but would always write notes to each other in English class. She was the only girl I knew back then that was curious about me on a personal level. Not even my girlfriend at the time asked me personal questions or tried getting to know me in that way. We did however wrote letters to each other and talked on the phone. But when we were together at school, we barely had a conversation. Our relationship didn’t last that long.
Fresh off a relationship, I just started asking these girls out I thought were pretty and cute. They agreed to going out with me, but when it came time for us to meet up at said location, not a single one of them showed up. I was hurt, and sad. To be 14/15 and ecstatic to go out with someone only to get stood up emotionally is just devastating. My spirit was crushed because it happened to me more than once. And pretty much from there, I went on the rest of my high school days living in disappointment and lacking confidence. Afraid to ask anyone else out because I’ll always think to myself, “what if I get stood up again?”
A Terrible Wingman
Wasted half my life on a friendship that should have ended a long time ago. But if I knew what I know now, we would have never been friends from the start. All things considered, he made a great Antagonist in the story of my life. I won’t call him by his name on here due to the fact I want nothing to do with him. There were definitely some scars left on me(mentally) from the friendship and it was still pretty recent when I chose not to talk to him anymore. I guess for the sake of this story, we’ll call him… Harvey(yes, like Harvey Dent a.k.a. Two-Face because that’s exactly how he played out to be in my life).
I met Harvey through my brother when I was about 13 or 14. Since my brother and I were really close and I didn’t have a whole lot of friends, I got to meet some of his. So, later down the road I would end up hanging out with Harvey just us at times, and I did get to meet his cousin who, I had a crush on for years. But nothing happened between us, just a little bit of sexual tension… I think. Anyway, there were several girls in my past that I did have a thing for, and I always thought that Harvey was such a great person because he had a way with words, and I was hoping he could help build me up with these girls. I would have to find out the hard way many times that it was not the case at all. As far as I knew, he only talked to them for himself. To the point where this girl I liked, he legit stole her from me. We ran into her at a bar downtown and I offered to buy her and her friends a round of drinks but he put it on his tab and took credit for it… and this was on my birthday! It didn’t end there either, despite him having kids with her. I met this really nice woman from a bowling league we had and by this time, I had gotten a lot better talking to women. And again, he would butt in and keep the conversation between them pushing me out. This was getting real old and it was only about a year after that I knew this friendship had to end.
Some of my closest friends would tell me how unfaithful he was and how poorly he treated me. I guess because when I met him at such a young age, my underdeveloped mind was processing information differently. There were countless times I knew he would make me feel awful and resent him as a friend. But something always brought me back to him. Now, I could go on and on about him but I’d rather not. Maybe I’ll save it for my autobiography I’m thinking about writing in the near future. Life has to go on, no matter who’s in it or not. Should have listened to my friends a lot sooner. But better late than never. And since I dropped him, I know I’m better for it.
Being a regular at restaurants and bars aren’t all bad, the servers will remember your drink orders. At least, that’s me of recent versus how I was, say, about 10 years ago. I was out with some old high school friends I hadn’t seen for a while and my goodness, my drink orders were the definition of a failed moment. It started off fine, just a water. Then I was craving something else, wanted to talk to our waitress more, so I ordered a lemonade. A little while after that and eating our food, I then decided to get a beer, just to make conversation. The routine I made of how I got to ordering these drinks was incredibly shocking… in a disastrous way. By this time, one of my buddies made fun of me for that, jokingly of course. It goes on my ‘epic fail’ moments. Let’s just call it a good lesson learned!
Not long after I turned 21 I went out with Harvey and some of his coworkers at the time to a restaurant to meet up with them. I was always really quiet, but who wouldn’t be? When you’re that young, and surrounded by people you don’t know, it’s difficult to make conversation especially when you’re an introvert. I have gotten much better at talking to people since though. So we’re out eating and having a few drinks, talking and laughing, then everyone wanted to change the mood a bit. Head to a bar with a dance floor. I met this sexy little minx named JC, as they called her. She was a friend of the coworkers. We locked eyes at one point on the floor and started dancing closer and closer together. This random guy saw us breaking it down and thought he should get in on the action(thinking there was going to be a dance-off). He goes a little over the top with his moves, leaving him to literally dance off of his shoe. Moments later, JC saw his shoe on the floor, grabbed it, and chucked it back at him, not realizing I was in the pathway between her and the guy. So this shoe hits me in the head and now I’m a little dazed and confused. JC immediately comes to me apologizing and then giving me a big hug that nearly sent us falling over. Unfortunately I would no longer see JC after that night. We never exchanged numbers or anything. But at least I was left with a good story and an interesting little moment.
A Friend’s Friend
I feel like we all have those friends that want to introduce you to one of their friends. In this situation, it’s always the friend’s girlfriend’s friend. Playing matchmaker. I can’t quite recall the occasion, but little did I know, I was going to meet my boo… Kait. Kait and I had one of those types of relationships; the sexual tension, an unspoken thing, and playing each other hot and cold. She was much better at the hot and cold thing than me. I was pretty bad at it. When we first met, she had this wild glowing look. Curly blond hair and red lipstick. She liked to stand out. But later would go to red hair, which to this day, I have no idea what her natural hair color is. We would watch basketball together rooting for the Bulls. This was during the time Derrick Rose was top dog. Back when the era of the NBA was, at least to me, at one of its’ highest peaks. Before all the big threes joined forces. Yeah, so we got together for that, out to the bars and even celebrated New Years. After waiting in line to get into the bar for a couple hours in the cold, we had just about 5 to 10 minutes before midnight. We were with one of my buddies I met from high school as well. Had a round of shots, the clock is ticking, and people are counting down from 10. And there we were. Eyes locked, almost midnight. Not certain if I should have gone in for the kiss when that hand hits 12…
Kait and I did quite a bit together. Watching sports, going out to the bars, clubs, to city events and watching a movie at my place in the dark with no one around. All of these and yet… I never made a move. Not even a single kiss despite many opportunities. I can’t really explain it, why we never happened. And now she’s married and has a child, which I’m very happy for her and her family. But after writing all of this about her, about us, I think I know what it was… that chase. I really do love it, and I’m not sure why or how I became that person. But eventually the chase has to end.
What Have We Learned
Whether I’m getting stood-up or dealing with issues at home, I know my friends always seemed to have my back. They were very supportive and lifted me up in a way I never thought. Even when I was at one of my lowest. Thank you all for being my friends. You guys know who you are. As far as hindsight goes, I seen it way too late that a girl from school had liked me while I’m busy telling her about another girl that I liked. So sorry Jaclyn. I saw the look in your eyes at prom and I thought the same thing. Maybe in an alternate Universe we could have been. Although I’m really slow in seeing these situations, I tend to learn many things the hard way. Like how some women give off very easy signs they like me and yet I still find myself unable to ask them out. It may have something to do with my past and being afraid to make that next move. Ladies, I’m definitely working on it! Just be patient with me a little while longer. With that, I do hope you enjoyed this read. It’s definitely one of my longer posts so far, but I am a better man for everything that has happened to me.