33 High School Boyfriends

 

Intro

I am not exactly sure when I became interested in boys, but once I did, they became a major force in my life.

Over the years, I had six serious boyfriends, along with many other relationships that were fun and enjoyable but never deeply serious.

I was naturally flirtatious. I enjoyed talking, laughing, and getting attention from the opposite sex. There was excitement in it — the spark of attraction, the feeling of being noticed and appreciated.

But underneath that was something simpler and deeper.

I wanted closeness. I wanted the comfort of hugs, cuddling, affection, and companionship — things I had loved from the time I was very young.

Physical affection felt reassuring to me. It made me feel connected, chosen, and loved. And so, as I moved through my teenage years and young adulthood, boys became woven into the story of my life — sometimes bringing happiness, sometimes heartbreak, but always teaching me something about myself.

Looking back now, I can see that I was searching for more than romance.

I was searching for warmth.

For connection.

For the feeling of being deeply seen and cherished.

And each relationship reflected back a different part of 

who I was becoming.

At first,

love looked like attention.

A smile across the room,

a hand reaching for mine,

arms wrapping around me

so I did not feel alone.

I chased closeness before I understood

what my heart was truly seeking.

But even then,

beneath every crush and every kiss,

there was the deeper longing:

to love,

and to be loved completely, forever.

First Loves

My first major boyfriend was when I was 14. He was attentive, kind, and very handsome, with dark hair and dark eyes. He was two years older than I was, which made him seem wonderfully mature and sophisticated to me at the time. We went “steady” and for about a year.

I was very much in love. There was excitement in having a real boyfriend — the dates, the attention, the feeling of belonging to someone and being chosen by them. 

Like many young girls, I imagined love lasting forever. But right before he left for university, he decided we should begin seeing other people.

I was heartbroken. At that age, first heartbreak feels enormous, as though the world itself has shifted beneath you. 

Fortunately, that summer, life opened in another direction. I became deeply involved with my Bayport group and met another boy who was four years older. I enjoyed being with him very much. He was smart, confident, fun, a great dancer, but the relationship was short-lived because my first boyfriend returned, saying he had made a mistake.

I agreed to give the relationship another try. Part of me wanted to recover what we had before — the closeness, the excitement, the dream of first love, but something had changed. Even though we reunited, things never quite felt the same again, and eventually we drifted apart.

After that, I leaned back into my Bayport friendships and the comfort of my social circle there.

Second Love

Then, in the middle of my junior year, I met another boy — handsome, blonde, big blue eyes, and newly arrived from Iowa. We dated and quickly became exclusive.

He was attentive, fun-loving, and easy to be with. We spent a great deal of time together and shared many happy experiences. Once again, I loved deeply and wholeheartedly.

At that age, I loved easily, but life was moving forward.

When I left for the University of Georgia in Athens, distance slowly softened the relationship. By Christmas, we had broken up.

Another love had come and gone.

And though each ending hurt at the time, each relationship carried its own gifts — lessons about longing, attachment, excitement, heartbreak, and the many ways the heart continues learning as we grow.

Poem

Young love burns brightly.

So quickly,

so completely.

We believe every feeling is forever,

every goodbye impossible.

But hearts grow through loving,

even when love does not last.

And each boy I loved

left behind more than memories.

They left small pieces of understanding

about myself,

about longing,

and about the kind of love

my soul was truly searching for.