Okay, fine. I was desperate. That’s the first step, right? Admitting the problem?

I’ve always fancied myself a reasonable man, if at times a little emotional. What’s more, the concern of finding a partner always struck me as a perfectly rational goal in life, never one of vanity or personal gain. Putting it bluntly, I was desperate for a girlfriend.

I greatly disdain the idea that a romantic partner is something that must be won like a game of cards. One false move and boom, all chances are shot. This puts pressure on to pay attention to your every move and worry about pushing it too far or falling a hair short of whatever the other person is seeking.

In the movies, awkwardness or shyness is cute and invites interest in a film’s romantic plot. In real life, though, those attributes are not considered inviting, but instead evoke weirdness or, even worse, creepiness. God, I wish I could switch places with the lovably dorky (and fancied) Scott Pilgrim or Peter Parker – someone like me would be swimming in romantic prospects.

So, it was prom season, and the hype was growing, as if exams weren’t enough for the universe to be lobbing at us. Everyone was doing their big promposals (I think that if the whole “promposal” idea disappeared completely and people just asked one another like normal human beings, no one would miss it) and couples were quickly pairing off. I was a junior, this was my first prom rodeo, and I didn’t know what the hell I was doing.

I saw an opportunity: the chance to finally ask out the cute girl I had a crush on. All year I was slowly getting to know her friends, becoming part of the gang, even being invited to the coveted Halloween party. Eventually her friends became my friends, and I started hanging out with them because I genuinely wanted to rather than for any half-baked scheme. I’d had previous experiences asking girls out on dates, but I knew this would be different. Did you see the way she smiled at me that one time? Obviously she likes me, right? I was set, I was asking her to prom, she would say yes, and we would live happily ever after.

The first step was securing a method. I knew it had to be something special since that’s the modus operandi at this point in prom history. I’m not a particularly creative person, especially when there have already been signs and gifts – even a friend of mine receiving baby ducks along with her promposal. I asked a friendly teacher if I could use his classroom after school. It was important to get her alone: I didn’t want surrounding pressures to influence her decision.

I put it off for days, a mixture of excitement and caution shaking and stirring in my head. Finally it was time. To clinch the deal, I had bought a box of chocolates to give her. While she was in her weekly club, I borrowed my teacher’s classroom and wrote “Will you go to prom with me?” in big letters on a projector slide and waited for my prey to become ensnared in my trap.

Club ended. Darting back and forth between the classroom, making plans with my point of contact, I nearly missed her. As I approached her, obviously both nervous and in a rush, my trademarked awkwardness reared its head.

“Hey, can I show you something?” I squeaked.

“Sure,” she replied, by some miracle.

I brought her into the classroom and my polite teacher, the only occupant, excused himself as naturally as he could – so basically as smoothly as a zebra in the Mariana Trench.

I turned to face her. This was it: I would ask her to prom, she would agree, we would hug, have a great time at prom, stay together through college, get married, and live happily ever after. Okay, maybe that was slightly unrealistic, but what can I say? Hindsight is indeed 20/20.

Forging ahead, I raised the projector screen, revealing my fateful request, pulled the box of chocolates out, got on one knee, and asked.

What is a good response to a question like “Will you go to prom with me?” Is it a casual “yes” or an enthusiastic embrace? Whatever it is, I can certainly tell you what it isn’t: panic. I can still almost hear the Price Is Right medley playing, the one where the price ain’t so right. Beyond just uncomfortable, she seemed genuinely afraid, as if she had just been put in the tightest spot of her life.

“I already promised a friend I would go with him.” Then, seeing my hesitation, she added, “He’s gay.”

Did that make the rejection any less? Not really.

“I’ll ask him if it’s okay and get back to you,” she said. This non-answer was clearly a tactic to bail from the pressure of the situation and put off the final letdown ’til later. But I put on a decent face.

“Yeah, sure. I totally understand. Whatever you want.”

We went separate ways; it would have been awkward if we’d spent the afternoon together, a cloud of intensely hot air hanging over her. I began to clean the whiteboard when my friends, who apparently had been spying on us, entered. I told them everything. We sat down in the student lounge to decompress (well, I was trying to, at least). After some time she came in and whispered in my ear, “Sorry, Joe, but the answer is no.”

It was loud enough so the others could easily hear, or at least infer, what she said.

“Okay, that’s totally fine.”

It wasn’t totally fine. All my effort, all my planning, all for naught. I would eventually find out from a close friend of hers that the main impetus for her refusal was that she simply didn’t want to go with me. I’m pretty sure she did have a gay-friend-date arrangement; that’s just the kind of person she is.

Still, I did gain something. Illumination. Insight into the fact that nothing is guaranteed. The best-laid plans, the most meticulous efforts, are all subject to humanity’s faults and can crumble like Oreos drowned in milk. That uncertainty should let us never take loss too seriously, to always strive to the next effort, the next plan in order to live our lives to the fullest. In order to truly live.

Maybe the chocolates were a bit much.