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Thursday, June 11, 2026

1996 Changed Everything: Pt. 4 - Love, High School Style



This is part of a series of articles about 1996, as it holds significance for me since it was the year I graduated high school. In this fourth article, I look at how a significant relationship influenced decisions whose ramifications I am still feeling to this day.

Love is a wonderful thing. Michael Bolton said so in his 1991 hit song. Hey, it ended up in the Top 5, so he must have been on to something. Before you truly know what love is and what love feels like, love can take many different forms.

It can take the form of innocent crushes on girls in your class, like I had several of during elementary school. It can take the form of infatuation and pining like I did for a girl who used to visit my neighborhood during the summers of my formative years. When you are chasing the type of secure love that your life has not given you much of, you start to settle. You start to think that maybe you should say yes to whoever comes knocking.

Looking back thirty years, I can say in all honesty that during the nearly three years I dated my high school girlfriend, I thought I loved her at some point. Using my wisdom and experience from those years that have passed, I can say that, no, I never truly loved her. At least not in the purest form. Not in the way that I would want to be loved.

We came together mostly out of convenience. She literally lived next door to me and was friends with my sister Kate. I hardly had to do any work in terms of courting her before we were together. In fact, it was Kate who bluntly stated that we both knew we liked each other and that we should just get together.

I remember on that cold winter evening in February 1996 thinking to myself: Wait, I like her? I think my reservations were overruled by the thought of actually having a girlfriend, which was something I’d been wanting for years. A girlfriend in 5th grade, or a brief connection over a summer or two, was not the real relationship I was looking for.

I decided, why not? Soon we were hanging out and getting to know each other. The time together grew, which meant that my time with my group of friends shrank. In my mind, I thought if they were really my friends, they’d be happy that I had a girlfriend. Maybe that kind of justification to myself should have been a warning sign.

I was a senior while my new girlfriend was a freshman. It was not ideal. It actually made me feel a little less-than. Sure, a freshman who dates a senior would be seen as stepping up. A senior dating a freshman? It was more of a ‘what you couldn’t find anyone in your grade?’

Her reaction to us being together was to sweetly say, ‘I can’t believe I’m with you.’ It appealed to my ego. Yeah, I am a catch, I knew it. But it was also a lot of pressure to live up to. Also, in the back of my mind, I should have read it as it was: I had settled for less than I should.

Now, don’t get me wrong, this is not a knock on her. She was sweet, funny, kind, and supportive. I’m looking at it from my perspective. If I felt the same way as she did, then I wouldn’t have opted against going to my Senior Prom. I couldn’t let my friends and classmates see I was dating a freshman. That’s on me, not on her. My insecurities and low self-esteem kept me from going to one of the milestone events of high school life. Maybe a few people would have cared. Looking back, I think that my group of friends, many of whom I am still in touch with today, would have been happy I was there.

I’m sure the next logical question is, why did you date her in the first place, then? Convenience, the desire to have a girlfriend, and an inability to say no. I should have said I didn’t have those same feelings. I didn’t want to be seen as the bad guy. Plus, the fact that she was so damn into me was intoxicating to a teenage boy who had not felt much love or appreciation at home for much of my childhood. I needed that validation.

Celebrating moments after my high school graduation in 1996.



The way that I viewed love and relationships as a teenager is far different from the way I view them today, as it should be. In my immature mind, it was about the fooling around every bit as much as it was the emotional connection. It was about availability over compatibility.

I know it was a me thing. Growing up, I was not taught how to give affection or express emotions. Vulnerability was weakness, at least in the presence of my first stepfather. I lost my ability to trust new people, always figuring they had an ulterior motive or were waiting for the right time to hurt me. I had done two bouts of therapy as a younger kid and probably could have used more.

For my girlfriend, I was the prize she couldn’t believe she’d won. She only wanted to be with me. I can’t speak for her, but I know that to any fully functioning adult, this would have spelled a perfect relationship. Unfortunately, I was the awful combination of an immature teenage boy and an abused child with emotional issues. I was broken, and she couldn’t fix me. She shouldn’t have had to.

An unexpected revelation about myself from this relationship was finding out just how broken I was. When senior year was still ongoing, I had structure. I couldn't spend unending amounts of time with my girlfriend, so I think things were masked. Once school was over, we spent more time together, but it was all pretty smooth. It wasn’t until my friends went off to college while I took a semester off that things started to go off the rails.

It wasn’t long until I felt I had made a mistake. Not so much in dating her, but making choices in my life based on our relationship. I had decided to take a semester off before going to college. Not only take a semester off, but also not go to, or even apply to, colleges that would have been off of Cape Cod. I still believe this to be one of the worst decisions of my life.

Despite it being more about convenience than actual feelings, my girlfriend made me feel important. We had some fun times. It wasn’t that I didn’t enjoy being with her, but our interest levels were far apart. I wanted to give it a chance, though. If I had left for college, then that would have been it. We’d have been a quick fling to end my high school days. Perhaps it should have been.

Dating in high school is a trip. Maybe you have a car. Maybe your parents have to be your driver. Maybe you have money for dinner or some sort of activity. Maybe you can only afford to go for a walk. Maybe you hold hands and talk on the phone. Maybe you go all the way. As a teenager, the possibilities were seemingly the entire spectrum of what life could throw at you.


That semester off to end 1996 was sobering. I went from a high school senior with possibly limitless potential to a lowly dishwasher/prep cook living at home. I can remember my life becoming a routine. Work, hanging with my girlfriend, rinse repeat.

I would drive us around in my mom’s station wagon, or later, my first car, a Pontiac Grand Prix. We’d find secluded places to, well, you know. We’d hit up Taco Bell and Burger King. It was being a teenager, but doing so while my future was slowly fading off into the horizon. It’s like I was blissfully ignorant.

A 1982 Pontiac Grand Pirx, my first car.



When my girlfriend was all that was left in my social circle, I started to cling tight. Familiarity was something I desperately needed as the rest of my life was descending into chaos. My mother wasn’t happy that I was spending all my time hanging out with my girlfriend and eating fast food, going so far as to point out the weight I had gained since summer ended.

Now I needed my girlfriend to become my anchor. What started as convenience morphed into toxic desperation. I felt less-than in life. I felt weak and powerless from years of abuse and neglect at the hands of my father and first stepfather. Having a girlfriend who idolized me made me feel strong and important. I began to lean more into that.

When you start to believe your own hype, it can prove to be your downfall. I have been a mix of different issues for so long. I have an avoidant attachment style. It’s a fear of intimacy and vulnerability stemming from my childhood. I also crave the closeness and safety of a real, loving relationship. It is two opposing forces colliding.

Now, in my late 40’s, I can see this and express it. When I was 18, 19, it was all there but also wrapped up in immaturity and teenage angst. I wanted my girlfriend to be there. I’d sing songs to her, and we’d go on late-night walks through our neighborhood. Then, if I felt I was lowering the mask too much, I’d flip on a dime and become cold and callous. It had to have been incredibly frustrating and confusing for her.

I look back 30 years, and on one hand, I am embarrassed at how I ended up becoming a bad boyfriend. Instead of saying no to the initial meetup, I became drunk on the attention this girl gave me. If my life were out of control, I wouldn’t just talk to her or someone else about it. I would lash out or be cold and distant as a way to express my inner turmoil. I probably trashed her mental health and self-esteem as she wondered what she was doing wrong. In reality, I needed therapy badly. I do wonder if it would have been the same result even if I were dating my biggest crush I had back then. Maybe nobody would have been able to make it work.

Then again, I look back to 1996 and step back to see a broader view of me, my life, and my mental state. I was 18. I knew nothing of real intimate relationships. It was all new to me. I didn’t go into that relationship seeking to hurt anyone. That’s not me making excuses; it’s me going a little easier on myself because of where I was in life at the time. When you don’t have a reference point for how to cultivate a relationship, or even how to properly express yourself, you are destined for trouble.


A lot of this particular post about 1996 is me admitting my faults and trying to atone for my actions. Today I am my own harshest critic. I was not the greatest high school boyfriend. Yes, she and I lasted a little over 2 ½ years, but honestly, the relationship should have ended a year before it did. We even had a brief split, but I went back to rekindle it. I guess I was desperate for any sense of normalcy. It ended up being a big mistake. In fact, that final year of our relationship might be why I look back on its entirety with such a bitter taste.

We were never meant to be a long-term thing. Statistics show that less than 2% of high school sweethearts end up getting married. So it was a near-certainty that I’d be writing about our relationship in the past tense as of now. I don’t know what the best-case scenario was, but I do know that in a different timeline, we’d have been joined together forever. There was a brief moment, a week at most, when I was 19, where we had to wait with bated breath for her to get her period. I have no idea how my life would have looked if that scenario had happened.

When she had finally taken as much of my bipolar attitude as she could, she ended things. Ironically, I was caught off guard and desperately clung to her to not leave me. Imagine that? I had spent nearly all of our relationship wondering if I’d made a mistake, and when she finally confirms my belief, I couldn’t accept it.

Today, I am single and have been for years. I would love to have the relationship of my dreams, but something holds me back. I feel today much like I did in those final months of 1996. I want the relationship, but also want my independence. That type of thought process is fine when you’re a teen. It’s not as good when you’re nearing 50. So I look at dating sites but stay in the background. Perhaps I am worried that version of me I’ve spent this blog talking about is still in there?


To tie a bow on this subject, let me flash back to 2012. This girlfriend and I had broken up in the summer of 1998. We had not spoken or even seen each other since. I was in the middle of training for my first marathon. I was out on a long run. Once I had put in enough miles running, I stopped, shut off my running app, and prepared to walk the remaining mile or so home. Then I spotted her.

She was standing outside her car in a parking lot. We both looked at each other. She seemed hesitant. I was exhausted, basking a bit in the runner’s high. I approached her, and we began creating some small talk. As we spoke, something was weighing on me. Knowing I might not get the chance to have her in front of me again, I finally gave her the vulnerability that she was owed from me.

I told her I needed to apologize to her. She said it wasn’t necessary and seemed like she didn’t want to go there. I needed it badly, though. I told her that my life was a mess then, and I took out my anger at that on her, and she didn’t deserve that. She deserved better, and I was sorry that I treated her that way. I was literally shaking from the nervousness of truly exposing myself.

She could have told me off, but she didn’t. She accepted my apology, which made me feel better. We left things off cordially and parted ways. I remember being in tears for the rest of my walk. It was a huge weight that was lifted off my heart. Yes, I had been a bad boyfriend, but I had grown from it, recognized my mistakes, and apologized from the heart. In life, that’s all you really can do.

1996 began with me at 18, single, in my senior year of high school, counting down the days until school was out. The year ended with me at 19, in a relationship that I wanted but also didn’t want. It was at the same time fun, exciting, a bit sexy, and a lot of confusing. It was all a part of the experience of growing up.

In the next post, I will go into detail about the other important type of relationship I had in 1996: my friendships. These were the people who shaped who I was, what I liked, and some of the fun memories that still hold a special place in my heart.



Home in 1996

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