A Visit to My High School Boyfriend & Unanswered Questions


I had thought of titling this as “A Visit to my High School Sweetheart,” rather than “Boyfriend.” It’s part of the effects of spending the week with my grandparents. The term is old fashioned, harmless, and more fitting to a generation where dates were shaped by “petting,” high waisted skirts, and an absence of bare shoulders – not akin to my suburban childhood in which we grew up making out in each other’s basement and being supremely confused about the whole fair, despite a burgeoning access to information on the internet about what others or doing or how things can be done. However, my adolescent questions never lied in the “how to,” but more in the “why not.” Visiting my high school boyfriend, on my week tour of my childhood state of Pennsylvania, I started to answer this question. 


What a Slut

Slut shaming

Slut shaming

My own high school relationship was stunted in that regard. It was a scandal among my particular group of friends when rumors spread that one of our own was handing out blowjobs like sweet tarts. “What a slut!” we’d chide, although I’d later learn it was so not my business to care what sexual escapades our sluttiest girlfriend was getting herself into.


This judgement likely had to do with our own lack of sexual experience. We were a bunch of prudes. My own experience through high school was limited to a questionable, one-off blowjob with my junior year boyfriend – questionable because my virgin ears had only learned the dictionary definition of “blowjob” the year before, and I had no idea what to actually do when there opportunity arose. Luckily we broke up not long after this and an incident in which his father walked down, unannounced, into the basement to catch his son with his hands under my uplifted shirt. šŸ˜±

If I remember right I blurted out, “It’s his fault,” pointing at his son with one arm, while the other arm tugged my shirt down. His dad smiled, turned right back around, and headed upstairs. My boyfriend and I stood staring at each other, toothy grinned, sightly aghast, but also greatly amused. I’m sure the rest of the night speaking with his father upstairs was awkward, but I was relieved to find nothing was significantly different.

dad walked in on me having sex with my boyfriend

It happens.

Back to the Point
My next high school boyfriend, the one who would

  • enchant me the whole of my senior year in high school
  • escort me to prom in his mom’s turquoise Toyota Camry
  • devastate me when we agreed to break up the first semester of college
  • move to Philly and echo back into my life – junior and senior year of college – mixed into my tangle of friends and serve as my sleep (purely sleep) partner, when I was too tired to leave the apartment of a mutual friend to go home at night to my actual boyfriend
  • be the first and only person to visit me at law school when I moved back northeast after a year in Miami

… was a prude too. Perfect!

Except it wasn’t…

Here we were: age 18. Hormones, anticipation, tension – and I couldn’t make out edgewise whether he never made a move because he was:

  • shy
  • disinterested
  • or religious

Nothing ever happened.

By the time he slept over in my room in law school it was too late. There were too many layers of our lives to sift through – the things we knew about each other, kind and unkind, and the mysteries and assumptions that build when you think you know someone and realize that you don’t. He knew I was lousy at being anyone’s girlfriend. I didn’t have enough self esteem to pick a winner, and so I didn’t date anyone I really cared about. For his part, when he left his religion, something wild, flickering and instinctual was lit inside him, and he became far too unpredictable  and wild for anyone to hold onto.

We’ve both come a long way in our development as empathetic human beings fit to be someone’s partner. Over a decade of dating and playing the field, but we eventually normalized the stunting effects of our own aberrant childhoods. My parents’ issues and divorce taught me to not trust anyone, so I always kept everyone close, but at arm’s length. It’s thanks to the patient men who dared try tame me into being their girlfriend, no matter how hard I tried to stay free of, what was in my mind, their reins. I’m curious as to his journey to this point and have no idea if he is dating, although my brief encounters make me think he’d be quite a catch if he’s come along as far as I have in being able to trust others.

Why Did We Bother to Date?

Reflection. 14 years later – nearly half my life, removed from the time when we began to date at age 17, I see odd crossed lines in the shared, happy-go-lucky, outward demeanor we both held above the building tension and confusion of our private family lives. Entrance into the threshold of rising social awareness and comparison one feels in their teens, we sought connection. We were such good friends, there was attraction, so why not? 

It’s funny now to see how social conventions guided us to try dating, when perhaps we could have been closer friends. There would have been a lot less pretension and confusion then. I wouldn’t have been disappointed and he wouldn’t have had to hear me rail at him. It would have been nice to have a steady, non-laced-with-expectation relationship with him all along.


It had been years since we reached out to other, but this past winter he accepted my invitation to come hang out with some high school friend at my grandpa’s house. He got to meet my husband, who was quite intrigued to meet the person in who I had been so invested much of my youth – and we all had such a great time together. Then a couple nights ago we hung out and talked all night, joking about his fear of AI, the volatile and the delicious sense of freedom, implicit in working as a freelancer – both our chosen bread and butter – over a course of pasta, Prego, and green bean casserole.

Pasta served on paper plates.

He cracks me up, and I find it so nice that despite the limitations of a small town school population, I somehow found someone who, over a decade later, I admire more than ever, and who, now that all the craziness of being single has ended in my life, I can purely enjoy as a friend. It’s one of the delightful side perks of being married. All possible pretense around make friends is cut, and friendship can simply be just that.