Edited by Barney R. Adjusted further by me. All errors are mine.

I have never lived up to other’s expectations

I am Carlton Adams Winthrop, only child of rich, snobbish, overachieving parents. I was a disappointment, at least to hear the ‘rents carry on. I must have disappointed Mary too, after all she looked elsewhere.

I was born in 1967. My parents never let me forget I was a disappointment. I was a straight A student, but because I did not become the valedictorian I was a failure. My high school career was not good enough nor exceptional enough because I graduated only third in my class of over 400.

I tried out for most of the varsity sports teams, but I wasn’t good enough to make any of the varsity teams, I was the first student to win four junior varsity letters. My father told me over and over that I was a wimp and a disappointment. It didn’t matter that I was a near scratch golfer, and could and did constantly whip his ass at tennis. Those were not varsity sports at our high school.

I was a disappointment as a son, because I chose to work after school and earn my own money. I was a computer whiz, and could program at a very high level, I designed several educational programs and single person shooter games that made me a multi-millionaire by the time I was 25.

My parents thought I was unfeeling and anti-social because I worked instead of living off their riches. I hated their social climbing show off set, and only went to the country club to play, or when I was forced by the ‘rents.

My dating and love life was nearly a complete bust in high school. The girls that wanted to date me from the country club set and were just looking at the dollar signs and not me. The girls from school that I dated; well nearly every time I went on a date, told me after that date or a few dates that I should not call her again. A couple of them didn’t say those words, but when I called they always said they were busy. I couldn’t even seem to attract the money hunters from the high school when I was in school.

That is all except Mary Agnes Calloway. Mary was a junior to my senior, she was smart, pretty, and had a smile that made you forget your name. On top of that, she decided that I was the one. She also came from a family that had more money than the city budget of the town we lived in. She was also a country clubber but a schoolmate.

As I said, Mary decided that I was the one. In early January of my senior year, she asked me to the Valentine’s Day Dance. That dance had a tradition of the girl asking the guy, and if he wasn’t in a relationship, he was expected to accept. I wasn’t, and I did. It was a first for me.

I was a disappointment to my parents when I didn’t ask for money for my date. I had already sold two lucrative, programs to an educational software company. I bought a brand new F-150 super cab pick-up and that furthered their disappointment. It wasn’t a luxury auto. It didn’t matter that it cost more than my dad’s new Beemer.

Mary was thrilled with my pickup. She told me it rode better than her dad’s Caddy. She especially liked the fact that I got the bench seat with the fold down armrest. It was never folded down when she was in the truck.

The dance was the start of a nine year on again and off again mating ritual. Mary and I were inseparable the rest of that year and through the summer. We spent every weekend together and she was my prom date. A whole lot of jaws at school dropped when the students realized that the awkward nerd had the prettiest and most popular girl in school on his arm.

She knew I was going to be going to college, and so when August came around, she asked that we take a break because I wouldn’t be able to come home every weekend.

Confused by this, I asked her; “Where do you think I am going to go to college.”

She said had never asked and told me she had no idea. Even with that broad hint and her response, she didn’t ask, so I did not enlighten her.

I told her it was her decision, but if we were to ‘take a break’ we should make it permanent as I must not be someone worth waiting for.

She looked down at the ground and quietly said; “That’s not what I meant. I felt that with you in college, and I still have my senior year in high school to do, that we would be apart more than we would be together.” Then she looked me in the eyes. “I want to enjoy my senior year, and you won’t be here for it.”

“OK, I am sorry to disappoint you that I won’t be spending another year with you. I love you, but if you feel we need the break, we will break. However, if you feel we need the break, you need to understand that we will not be getting back together until I, that’s right, I decide the break is over if it ever is. Now do you want a break?”

“Yes.” Was all she said. I paid for the dinner we never ate and took her home.

I had received full ride scholarship offers to MIT, Case Western, University of Chicago and the U of M. I went to the University of Michigan and turned my scholarship back so someone who was equally deserving but needed resources could come. I chose U of M because I wouldn’t have to be too far from home and their computer programs were more in line with what I wanted to study. When I got there, I found that most of the students and teachers did not feel a successful programmer was a disappointment.

I also found that other than when I was studying, I could always find a group of people to hang out with. Studying came first, and with my course load, I was not an every night partier. I made it home five out of every six weekends. I also discovered the ‘joy of sex’, and ended up with several (3) FWB relationships that I enjoyed immensely and often. The girls all knew each other and they all knew that it was only friends.

As I said, I was able to go back home almost every weekend. Mary wasted no time in replacing me. I saw her at the first of the high school sports events that I attended with a new boy. Every time I was in town I saw that she always was with a boy, or man, if a high school student can be called a man. I was often with a girl from school as we were only a 20 minute drive from my home. Mary didn’t look too happy whenever I showed up with a date. I even went to the homecoming dance. My date for that night was Sally Raymer. She had been in my class, and also had a scholarship to U of M. Unknown to Mary, and to almost everyone else, Sally was and is an ‘in the closet’ lesbian. I knew it, and it didn’t matter, she was a fun girl, and a great date, albeit without sex.

I was home for Christmas break, when my mother, the same one that thought I was such a disappointment, decided to try to intervene between Mary and I. She invited Mary to a couple of dinners with the family. I was not impolite, but I made a point to find a seat away from Mary, and did not start any conversations with her. I answered any questions she asked me with as short an answer as I could.

Mom was pissed and told me so, so the day after Christmas I returned to campus. Classes didn’t start for another week, and I didn’t care. I knew what I was to them at home, and I could do nothing to change their minds. But I didn’t have to have it shoved in my face anymore.

I finally went home for the first time since that incident during spring break my sophomore year. I went home for two reasons, my mother was diagnosed with terminal cancer, and I was not one to go to Florida or Arizona for my breaks. Mother was told she only had a few months to live, and she wanted to mend fences with me.

“Carl, (she never called me Carl) I want you to know that I am sorry for the treatment we gave you when you were growing up. Your father decided that by seeming to be unsatisfied with your achievements you would work harder. Unfortunately, it worked, and it also became easy for us to continue the ridicule. You were the son we didn’t deserve, you were a high achieving, caring boy who tried too hard to please his stupid, hurtful parents.”

“I want you to know that when you stormed out of the house last year at Christmas and not talking to us until I called two weeks ago caused me to think of what we did to you. I’m sorry, and if I could turn back time I would be a more involved, caring and loving mother.”

Then she proceeded to tell me about the huge fight with my father because of her change of heart. She had filed for a divorce, and discovered, from dad, in one of his rants, of his being a long term affair with one of his male employees. She then told me of his being discovered by one of the other employees and when confronted he quit and left town. She hadn’t heard from him for over two months.

When it all settled down, mother told me that all of their assets except my father’s 401k and a small insurance settlement were hers, and when she died it was coming to me.

I know it shouldn’t have, but that pissed me off. “I’m supposed to suddenly become a model son because your money is supposed to make up for the hurtful comments and put downs I had to endure. I tried and tried to make you and father proud of me. I made my first million while I was in High school. Take your money and put it where the sun doesn’t shine.”

I stormed out of the house and did something I swore I would never do again. I cried for my mother, for myself, and for all the hurts that were now right in front of me again.

I temporarily withdrew from school with the assurance that as soon as my family problems were finished I could and would return. I stayed with mother until she died, it wasn’t a few months, it was only six weeks.

At the funeral, Mary came up to me and asked to talk. I couldn’t be as impolite as I wanted, so I very quietly asked, “Please go away, I don’t need any more hurt today. The last time we talked, you tossed me to the side of the road like an empty candy wrapper. Please just leave me alone and go back to the latest boy or man or goat you are with this week.”

She reacted like I slapped her. She then turned and walked away. I didn’t see her again until after mom’s lawyer told me I needed to be in his offices for the reading of mom’s will. He added that I was the only other affected heir that he had to inform before he gathered both of us for the reading.

I wondered who the other one might be. I had a sinking feeling in my stomach that I knew, but I decided to wait until I was there to find out.

At 9:00 Monday morning, two weeks after mom was buried in the family plot, I was at the offices of Thomas Hardly, Esq. Attorney At Law. I walked in and my worst speculations were confirmed. Mary was there as well.

The will was read, and I got everything except a couple of signed paintings that Mary had expressed an appreciation for. The reproductions turned out to not be copies, but originals worth a good deal of money.

The rest of the estate turned out to be much more than I thought, and mother had put over 30 million dollars in a trust fund for me to be mine when I was 25, married, or graduated from college. I was also given a separate annuity that was the equivalent of $1,500,000 a year for the rest of my college life. It would then be increased by the amount of money I earned each tax year. I was stunned.

I looked at Mary, she looked very uncomfortable and like I had hurt her badly. I decided that it wouldn’t kill me to try to make up for my angry words.

“Mary,” I started, “Would you please have a coffee or dinner with me. I need to clear the air with you. Please, I was hurtful and said things that were on my mind, but that did not need to be said. And definitely not in the way I said them at the funeral parlor.”

She just nodded and whispered; “When?

“How about as soon as I get out of here, I have some papers to sign and banking to do, but I should be done by 2:30. Why don’t I call you and I will come by and pick you up or we can meet at a place you choose?”

“OK” Then she gave me her phone number.

I finished my business with mom’s lawyer, and put the first check in the bank. I had enough money on hand that I didn’t take any out. I thought that I probably wouldn’t for a couple of months.

I called and met Mary at her house and we went to a local coffee shop. Over coffee and a couple of cookies we talked for a couple of hours.

We made a lot of small talk, then, after catching each other up, and Mary apologizing for the tenth time I said; “Mary, We would not be in this mess if you had only asked me where I was going to school before you wanted to break up. You wanting that break made me angry. I was home almost every weekend of your senior year; I would have gladly taken you to all the important events. I used Sally as a convenient date for homecoming and when I wanted to go somewhere and she was available. Believe me none of those ladies were taking your place.”

She then responded, “I knew as soon as I saw the hurt on your face I messed up. The guys you saw me with were all one and done. I couldn’t find the next you. When your mother let me know of you going to the U of M, I knew that I really, really messed up. I’m so sorry, but I was so ashamed of what I had done that I couldn’t try to make up with you.”

“I was and still am angry that you threw me away, but I still shouldn’t have gone off on you at the funeral home. I want you to know how much of a mistake that was. In am truly sorry.

Now before we get too far into our reunion, and now that you’re going to college, are we still taking a break, or have you decided I’m OK because I can entertain you on weekends?”

“I don’t know,” she responded, “You said the break would last until you decided it was over. Is it over?”

“Well, seeing as you are now in collage, we won’t be able to get together and I want to enjoy my college time and have fun, so, no it is not over.”

She angrily said; “But I’m going to the same school you are.”

That made me start to get angry all over again. So with some heat I responded; “Yes, and if you had asked where I was going to school, we would not be having the break in the first place. I am still angry that you decided for both of us that I was not going to be available.”

She got up and went to the ladies’ room. I paid the bill and waited for her to come out. She didn’t, and I saw a cab pull up in front and she got into it. I guess I let my anger get to me again.

I went back to school after only losing one semester. I completed all of the classes I withdrew from. I only saw Mary a couple of times, but that wasn’t too unusual, there were over 25,000 students on campus at any one time.

I graduated with a double major a degree in computer science, and another in secondary education. I didn’t need the money, but I was not one to sit around, so teaching was my fallback position. I enjoyed it, and I did my student teaching at my old high school.

I saw Mary occasionally in town and at some weekend events. She was now a college senior and would be graduating the following May. I hadn’t talked to her in over two years, and was not about to start again. I seemed to get angrier the more I thought of her, and neither of us deserved to have that happen again. Me because it bothers my conscience; Mary, because I felt my actions toward her were hurtful.

After I graduated, I came home and lived in the family home. I had rented it out for my remaining college time and had the lease set up so it was done when I left college.

Well, the best laid plans

I wasn’t keeping myself busy with my programming, and I had turned down all of the computer programming job offers I received since my senior year in college, so a year after I graduated I checked and my teaching certificate was still valid. I applied for a teaching position with the all of the local school districts.

I was offered a position at a charter academy and while the salary was not the same as the public school teachers were paid, I took the job. I was assigned to teach classes in basic and advanced computer usage and beginning programming.