Thoughts on reading my love letters to my high school girlfriend after 30 years

October 8, 2019 by Joshua
in Choosing/Decision-Making, Relationships

Following up my posts Mementos of my high school girlfriend and The Most Romantic Thing I Ever Did, I finally read the letters and cards from her to me and from me to her. We wrote them from around the summer of 1988, after graduating high school, to about a year later, the summer after our first years in college. She went to school outside Boston. I went to school in Manhattan.


For about a year and a half before then she and I talked on the phone a few nights a week for a few hours. I think my phone was rotary.

We were each other’s first love. The time was my first on my own, struggling for independence, especially from my father, whom I considered authoritarian. The summer of ’88 I rode my bike with a friend from Philadelphia to Maine and back. The following summer I traveled alone to Paris, visiting Amsterdam. Here’s one of the postcards I sent from Paris.

I was getting into sports seriously for the first time.

What I noticed

More than anything about the relationship, I noticed my purposelessness. I didn’t notice it at the time, but it formed the backdrop of the times.

For example, I took classes because I was in college and they were offered. I didn’t know why. I just followed a path created by someone else. Didn’t create or take initiative. I accepted a structure for what to do — go to college, get good grades — no looking past what was presented.

For as long as I can remember, people have called me smart. Looking at these letters, I don’t know why anyone would say so. I see no special intelligence, insight, or value in what I wrote. A lot of it was boring.

I bought mainstream views of masculinity being wrong, bad, or shameful, especially around sex. I apologized to her for things like feeling physically attracted to her. I lacked assertiveness and confidence, let alone dominance. I misunderstood those concepts and their relations with masculinity.

To some extent you could say that 17-year-olds haven’t yet learned assertiveness and confidence, but reading them reminds me that I lacked them at least a decade longer.

Mainstream media today suggests that young men today face greater challenges because many stigmatize and misunderstand masculinity, but that’s a topic for another post.

I was starting to learn some lessons of sport: fun, discipline, team-based friendships, glory, pain, reaching and exploring my potential. Still, for what I learned, I didn’t yet learn competition or challenging my beliefs about my potential to extend it. I hadn’t developed a killer instinct, or a drive to win in fair competition.

Again, I took classes because they were offered, not for internal reasons. With one exception: I chose to take physics even then. It wasn’t required and I didn’t start majoring in it until my junior year, after my year off in Paris.

On the other hand, given the structure society presented me, I succeeded at it — that is, I took challenging classes, a lot of them, and succeeded at them. Actually, I didn’t read as much as I was assigned. I also read an essay I wrote for freshman writing that I photocopied and sent her. Cringeworthy.

A couple letters showed me struggling with my father and control. I felt he was controlling me in a domineering, nonsensical way.

I was still eating meat and drinking soda without seeing problems with it. It’s weird to see my handwriting describe me as drinking a Pepsi or hamburger. I don’t remember the last time those things registered as food to me. I can’t remember the last time I thought of soda as not disgusting.

Likewise, I saw myself enjoying religion, though I didn’t see myself thinking or acting on my own. I seemed to follow what society presented to me.

I saw myself struggling with love and desire. I saw myself confusing what I felt for her with what love songs said love was. I was trying to conform to a romanticized idea of love, distracting me from my actual feelings.

I expected relationships to work like The Princess Bride, or whatever media came out then, and was frustrated they didn’t. Instead of paying attention to the world and learning about people, their desires and struggles, etc, I tried to maneuver myself and others to fit that model.

Songs showed up a lot. I kept telling her what songs were on the radio while I wrote, suggesting the emotions I felt. I thought I was expressing myself through songs. Now I would say I was not learning to express myself but instead identifying emotions in others and just referring to it.

I gave her a lot of attention — too much hanging on, not leading a life a girl I would want in my life would be attracted to. I tried to keep her instead of living purposefully by what I care about, which is what I find most attractive and would want a partner to love me for now.

I looked to be missing a lot of what I consider important as a man: initiative, dominance (not domineering), assertiveness, listening, discovering, confidence.

I’m sure more will come up as I reflect more and I’ll update this page periodically. I don’t know how open or vulnerable this post read, but rarely do I share things like this. I’m not going to share the actual text, which are too embarrassing, so I’m not sure how abstract my observations read to others.

Since I read the originals, and wrote about half of them, everything seems clear to me, but I’m not sure if it does to others.

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2 responses on “Thoughts on reading my love letters to my high school girlfriend after 30 years

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