I possess the ability to talk myself out of anything.

Doesn’t matter how much I want it, my brain convinces me I shouldn’t go for it…then berates me mercilessly after the fact for not chasing whatever it was I initially wanted. And by then, the opportunity has passed. I missed out, and I’m left wondering what might have been.

This is one such story. And as the title suggests, this a story which has recurred in my life more times than I would care to admit. Sure, the circumstances change, as do the people involved and the desired object or outcome.

But the result remains constant: complete and utter self-imposed disappointment.

It was July of 1998, the summer between my freshman and sophomore year of high school. I was taking a summer-school Geometry class so I could take Algebra 2 the following fall with one of my favorite teachers from the previous school year.

Sitting in an un-air-conditioned classroom with 35 other students for six weeks during summer in Sacramento was a dozen kinds of miserable.

But, summer classes were co-ed. And when you’re a student at an all-male Catholic high school, opportunities to meet girls are hard to come by.

I showed up to the first day of summer school Geometry, half-asleep (it was 8:15am on a summer day – by rights, I should have still been in bed) and dreading having to do summer training for football that afternoon in the sweltering heat and humidity.

We were assigned seats alphabetically, and mine was at the back of the room. I was still rubbing the sleep from my eyes when the most beautiful girl I’d seen at that point in my young life sat down in front of me. Tall, with long strawberry blonde hair, a slender build, and legs that reached up to the Oregon border. Looking back on it, she looked a lot like Blake Lively.

Immediately, I went mute. I wanted to talk to her, but I couldn’t find the words or summon the courage.

My mind began nagging at me. “Talk to her, you dope! Just say ‘hi!’ What’s the worst that can happen?”

Humiliation. Self-doubt. Awkward moments. People pointing and laughing.

These are the things that could, and had previously happened that made me so risk averse.

So I said nothing.

Three days went by and I hadn’t participated in class at all. The girl in front of me, to whom I still hadn’t spoken, likely thought I was mute at that point. But, as we were getting back our first quizzes, she turned toward me, a frown on her face and holding a paper covered in red ink, and asked, “Do you get this stuff?”

Oh no, she’s talking to me! What do I do? What do I say? What if I say the wrong thing? What if I open my mouth and the dam breaks, and I tell her that I’ve developed a tremendous crush on her based solely on her physical appearance (because, being primarily visual animals, that’s what teenage boys do) and she faints at both my audacity and general physical repulsiveness (a girl I’d liked in 6th grade once took it upon herself to inform me of how stomach-churningly repulsive I was after I told her I liked her). Then I’m for sure ending up explaining myself in the Dean’s office and getting expelled, which will result in my parents actually killing me dead.

Or so I thought.

I shook my head and held up my own quiz, marked up with so much red ink it resembled a crime scene.

She pushed her frown to the side of her mouth. It was absolutely adorable.

“Why are we so bad at this?” she asked.

“Because Geometry isn’t algebra. Because it seems more theoretical than practical. Because we’ve never done geometric proofs before, and we don’t see the need to provide the theories postulating why a triangle has three sides…” is what I wish I would have said.

Instead, what came out was, “I dunno.”

Unsatisfied, she faced forward again.

Well, that was about as smooth as a gravel road.

As everyone got up to go to morning break, our teacher called her, me, and a third student over. He said something about his concerns for how badly we’d done on the quiz, that he was available if we needed help, and that maybe we could find some other students to study with. Admittedly, I was itching to get out of the stuffy classroom, find my friends, and tell them I said actual words (sort of) to the girl I wouldn’t shut up about. But before I could escape the room, she stopped me.

“You want to try and figure this out together?” she asked.

Something within me screamed, “Say ‘yes,’ you moron! Golden opportunities like this…well, this might be the only one you ever get!”

“Yeah, that would be great,” I managed to say.

“Cool.” She smiled and gave me a small wave. “I’m Dina, by the way.”

“Matt,” I said.

“Nice to meet you.” She flitted out the door.

I stood there like a meat-statue struggling to process what the hell just happened.

“Close your mouth. You’ll swallow flies,” my teacher said as he approached. He patted me on the shoulder and smiled. “It’s ok. Work at it. You’ll get it eventually.”

To this day, I don’t know if he was referring to the math or matters of the heart.

Dina and I started meeting up before class, after class, sometimes during the lunch break I had before I went to football practice, comparing homework and working through the concepts we both struggled to grasp.

More than that, we started getting to know one another. She was funny and kind. Though she wasn’t good at math, she was good at most other subjects. If I remember correctly, I believe she was either on the swim team or the debate team or something like that. She also did things like remember my name and look me in the eyes when we talked – not always a given when I tried to talk with girls at that point in time.

What started out as a crush quickly escalated to full blown feelings. And what sealed that was, one afternoon, we went off campus and got lunch together.

After class, we walked to a nearby Burger King. Tired of talking about school and geometric proofs and other things that made our heads hurt, we talked at length about our lives. She told me about the colleges she wanted to apply to, about a trip to the beach with friends she was looking forward to once summer school was over, and an annoying younger brother who she had, the night before, threatened with a rolled up magazine because he wouldn’t leave her alone.

I related a similar story about my younger sister.

We laughed. She had a great laugh, and man, how I loved to see her smile.

She asked me about football, since I’d been complaining about afternoon practices, and had one coming up in an hour.

Side note. It is NOT a good idea to eat a Whopper and fries before engaging in 3 hours of strenuous exercise. Just…take my word on that.

Anyway, I don’t know why I said it, but I off-handedly told Dina, “I hope my dad can come to some of my games this year.”

She turned to me and, with genuine curiosity, said, “Why?”

I shrugged. “He came to one quarter of one game last year, and we were already way ahead, so I wasn’t even playing.” Not a humble brag, I swear.

“Why?” she repeated.

“Well, he’s busy with work, and trying to go back to school, and other things. And he and my mom are kind of separated right now…” I stopped. I’d said too much. I didn’t know why I expected her to react negatively to my saying that, but I clammed up to keep myself from making it worse.

Instead, she looked over at me as we walked, concern in her eyes, and said, “Tell me about it.”

So I did.

And she listened. What surprised me most was how easy it was to talk to her. She listened like a friend would. Well, not like my friends would. Don’t get me wrong, I had a group of friends who were like brothers to me. But listening to heavy matters wasn’t their strong suit, and none of us were capable of doing so without crowbarring in a few dick jokes or Simpsons references.

Dina was different. She listened without judgement, without making it awkward, and without making me feel bad about it.

That was the day I fell for her.

However, there was one small, but growing problem.

Summer school was almost over. Soon, we wouldn’t see each other every day, and I began to wonder if the connection we’d been building would be severed by a lack of close proximity.

I wanted her to be my girlfriend, but I wasn’t sure if she felt the same way. And still being the immature dunce I was, I wasn’t sure I could be “just friends” with her. It would take almost a decade of maturation and life experience before I was capable of that.

Looking back, there were plenty of opportunities to ask her if she shared my feelings, or, at the very least, ask her for her phone number.

But I put it off and put it off until, finally, the last day of class came around. I was nervous, but also a little relieved because today had to be the day. If nothing else, I would be forced into it by the sound of the buzzer – the buzzer being the bell signaling the end of the class period of the last day of class.

A few minutes before noon, the buzzer sounded. Everyone in class shuffled out. Dina hung around and we chatted briefly about how we thought we did on our final exam.

I rallied what courage I could, doing my best to keep the negative “what ifs” at bay, though they were struggling mightily to free themselves.

Well, here goes…something.

“Uh, Dina?”

“Yeah?” She waited patiently for me to continue.

This was it. Now or never.

“I just wanted…” I stopped.

Oh no. Words. I need words. Come on, I’ve been practicing all week!

I felt the pressure building. All my doubts were pressing against my mental reservoir, railing to free themselves. Cracks began spreading across the dam’s surface. Somewhere in the back of my mind, I heard a voice shouting, “Take cover! It’s gonna blow!”

My face went red. “What I mean to say is…”

The dam burst. And all the things I’d worried about the first time I saw her drowned what little confidence I had.

“Have a good rest of your summer,” I said.

She gave me a weak smile “Yeah. You too.”

We both stood there in some of the most awkward silence I’ve been unfortunate enough to live through.

“Ok, well, I’m gonna go,” she finally said.

“Yeah, ok. Cool.”

She turned and left the room. And as she walked away, I stood there, dumbfounded by what just happened.

Five years from this point, Captain Jack Sparrow (Jonny Depp) would later say to Will Turner (Orlando Bloom), “If you were waiting for the opportune moment…that was it.”

Standing there watching Dina disappear out of the classroom, I knew my opportune moment had come…and I’d blown it.

I never saw her again.

To this day, I wonder how things would have been different had I just asked for her phone number. Maybe nothing would have come of it. Maybe we’d have dated for a while. Maybe longer. Maybe not at all. Maybe we would have ended up as good friends or distant acquaintances.

Maybe, maybe, maybe…

All these years later, I wonder what could have been.

And I kick myself at the uncertainty of unrealized possibilities resulting from my ability to talk myself out of going for something I really wanted.

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