Life is full of regrets.
They say that they shouldn't overwhelm you, and I agree with that. I don't sit in my room crying over past mistakes, but I do find myself in random situations thinking about them - like when i'm sitting in traffic or waiting at the airport. I'm glad with most of the decisions in my life, and even some of my regrets are silly but I always wonder.
One of my regrets was my choice not to try out for high school basketball. I went to a all-boys, private, Catholic High School, and I played basketball for fun during childhood, and was on the 8th Grade basketball team. I was average, my large height gave me an advantage, but I was like most other tall kids - bad at dribbling and too skinny to hold my own in the post. It would be like Todd Pinkston playing for the Sixers.
In the high school during my freshman year of 1996 were a few freshmen who were obviously better than me, and even courted by the school to attend and play basketball. I wasn't one of those kids, but from day one every teacher would call me: "Kevin's brother".
You see, Kevin was the basketball star at our high school. When I entered the school freshman year, he was a senior. Expectations were high that year for his team to win the Catholic League Championships, and there was a lot of pride and pressure that went along with being on the team.
That pride and pressure also trickled down to his little brother. It made me nervous, because I thought I wasn't as good as Kevin, since he was the golden child of sports who played little league basketball and baseball, while I was in his shadow. I will be honest, sports at the time didn't hold as much interest for me. I was more interested in playing on my Commodore 64 or Atari. His weekends with the neighborhood kids were spent outside playing the "sports of the season". In summer they would play baseball; fall would be football and street hockey; spring was basketball. My weekends with the neighborhood kids were sleepovers were we would play Dungeons & Dragons until 2am drinking Mountain Dew, eating that new invention: microwave "Pop Secret" butter popcorn and trying that new pizza delivery service "Domino's Pizza".
Why all this information? Just to build up the factors behind my regret. You see I was actually going to try out for the basketball team, and I didn't really announce it to anyone. I thought that I had a shot, and with the proper training that I could have made it.
I remember walking down the hallway towards the doors of the open gym, it was late September and the sun was shining brightly through the hallway windows. There were already some kids on the court taking shots, and dribbling the ball. As I walked closer a cold feeling of dread started in my stomach, and I got scared.
I walked past the open doors, and headed outside to the main entrance. I waited for the bus and went home. That was it. My chance was over, and in a instant moment of fear and insecurity I walked away from the tryout. I still think about that day, and don't really know if I would have made the team - in all honesty, there were much better players than me on that court and my chances to make the team I would give about 25%.
Life goes on. I think my regret is more of a wistful regret of just not trying, and running away from my fear. There has been other times that I didn't do something in my life which was driven by a shy insecurity. I look back on some of these decisions that I made and wonder what could have been.
A second regret I have is, again, silly to me. A friend of my father was a semi-prominent lawyer who lived in Old City Philadelphia. He had three children, one of them, a beautiful blonde haired daughter named Stacey, who was my age. My father told me one day that Stacey didn't have a date to the prom and I should call her - I forget his exact words but it was easily implied that she would go with me to the prom.
I called her, and we spoke on the phone for about 30 minutes. I was nervous and my major dealings with women, at that time, was extremely limited. If you read my first entry, I moved to this new isolated neighborhood in 8th grade and went to all all-boys high school. I know this is starting to sound like something from Dr. Phil.
I don't really remember the conversation. I do remember I was in the basement of our home, dubbed "The Apartment", and that I did agree to go see a movie with her and she did express interest in going to the prom. I really never met her before, maybe once or twice, but I do remember she was intelligent, beautiful and very nice. The next week I drove into Old City and picked her up.
It was something out of a Disney movie when she opened the door at her father's townhome. I half expected a turtledove to land on my shoulder and say to me "You're screwed".
She was hot. I was self conscious and had like NO experience with girls unless you count watching The Playboy Channel. I felt really nervous, and made some simple small talk on our way to the movie. Walking back outside to my Jeep Wrangler, I notice that there is a ticket on my car and she smiles, walked up to my car and grabbed the ticket.
"Cool, now we can park illegally at the theater.", she said.
"What? Won't I get towed?", I inquired.
"Nah, just park where I show you and we will put the ticket back on the windshield and they will never know the difference.", she chimed in.
Beautiful. Intelligent. Nice. AND COOL.
The night itself went well enough, I drove her home, but bailed on even trying to kiss her. Yea, I wimped out.
Of course that was just the one regret. My second regret was that I think I spoke to her on the phone two times more, but I never really talked about the prom or making plans for it. I am nearly positive to this day that she would have went with me, and again - my shy insecurity won out. I didn't ask her and basically really never called her again.
The prom came and passed and my father said to me one night, "Hey what ever happened with Stacey? Why didn't you ask her out?"
I told him that I wimped out and never asked her.
His reply still stings to this day, and even years later he told me how sorry he was for even saying it.
"Yea, she's out of your league, anyhow."
Ouch. Thanks, Dad.
I regret not asking Stacey to my prom. I never went to the prom, but then again - I didn't have many CLOSE friends in high school and since it was all boys it was much harder to even find a date for me. I did run into Stacey a few times over the course of the next couple of years. She went on to study at Columbia University and from what I heard from my father through her father is that she was constantly dating bad boys that her father hated. Every time I would see him he would tell me how she and I would be great for each other.
Maybe he was right. Damn. What ever happened to her phone number...