Reunion with high school crush turns awkward due to unexpected bill drama
Years later, my high school crush asked me out on a date to a restaurant, but when it came time to pay the bill, I couldn’t speak.
It was like a scene out of a romance comedy meeting up with my high school love interest, Jason, again at a fine restaurant. But the evening took a somber turn as his charming exterior revealed a stunning secret that hit me like a ton of bricks. The boy I had admired was no longer there, and his replacement was someone I barely knew.
Hi to everyone here. My name is Emma, and I’m 35 years old. My history goes all the way back to my time in high school. I used to be the reserved, bookish girl who favored studying in the library than going out to parties. I was seriously infatuated with Jason, the school’s golden boy. Jason was attractive, popular, and seemed to have it all.
My closest friend Sarah would poke me when she spotted Jason out and about, saying, “Emma, come on, you have to at least try talking to him.”
I used to flush uncontrollably and hide behind my large specs. “Sarah, you know he’s not in my league. I am just who I am.
“Emma, you’re amazing.” “He’d be lucky to know you,” she would counter, but I would just shake my head.
With his friends all around him, Jason never once glanced in my direction. He was the star player on the football team and the life of the party. I watched from a distance, sure he had no idea I was even here.
I didn’t think he would see me wearing glasses and braces. Besides, he never did. Our worlds were very different.
Years later, I was a stunningly successful lady. I traded in my glasses for contacts, my braces for a perfect smile, and my nerdy attire for a stylish appearance. I was living my greatest life, having made a great career out of marketing.
One evening while picking out avocados at the grocery store, I recognized a voice.
“Emma? Is that you?
I turned to look at Jason, who looked a little older but was still really handsome. He was staring at me, incredulous. “Wow, you look amazing,” he said, his eyes wide.
Jonathan? Hi there! It’s been a long time,” I said, my heart racing.
He gave me a big smile. It has, in fact, happened. “How are things going for you?”
We had a lengthy talk during which we caught up on each other’s lives. I informed him about my occupation and my recent return to the region.
So you work in marketing now? That’s impressive, Jason said with a nod.
“And you?” I questioned, wondering what he planned to do after high school.
He laughed and sidestepped my question, saying, “My work is interesting, but it’s not as glamorous as marketing.” Why did he act in such way? As I was still processing his response, he took me by surprise with an unanticipated proposal.
Hey, how about we have dinner together at some point? You know, catch up appropriately?
I nodded without thinking. Jason was the one! He was also inviting me out on a date! Of course, I said, “Yes.”
A few days later, we met at an elegant restaurant in the heart of the city. His choice of restaurant was impressive; it was a sophisticated place with delicious food. Jason began reminiscing about our high school days as we were putting our meals.
Remember when we won the football championship? He laughed, “Man, those were the good old days.” “I still hang out with the guys on the team.” We have a little ritual where we get together once a month.
Despite my polite listening, I couldn’t help but feel a little detached. While Jason appeared to be stuck in the past, I had moved on from my high school experience.
“That sounds nice,” I answered, forcing a smile. “Are you ever reunited with anyone from your school days?”
“Not really,” he shrugged and answered. Just the dudes. What say you, too? Do you have any special memories from high school?
“Well,” I responded, unsure of what to say, “I spend a lot of time in the library.” Not many notable stories may be found there.
He laughed. “I remember you being engrossed in a book all the time. Isn’t it ironic how things change?
We continued our talk as our dinner arrived. Jason’s stories were getting boring, and I saw that I was falling asleep. I excused myself to visit the restroom as soon as dessert was served.
Jason was fiddling with something on my plate when I returned. Before I could ask him what he was doing, he looked up with a mischievous smile.
“Observe this,” he said, and brushed a hair across my plate. “I will demonstrate a trick for you.”
Before I could protest, Jason motioned for the waitress to come over as my eyes widened with horror.
He said, “I’m sorry, but it looks like there’s a hair in my friend’s food,” loudly enough to get noticed. “This is not appropriate!”
The waitress was quite sorry and apologized profusely. She promised to return the old plates and get us new ones. However, Jason argued that we shouldn’t be required to pay for the meals due to the inconvenience. After a bit of back and forth, the manager did show up and agreed to pay us back for our dinners and give us a free dessert.
As we left the restaurant, Jason’s joy was contagious. You’re familiar with handling these kinds of places. One should never have to make up for a bad experience.
With my brain still spinning from what had happened, I faked a smile. “It’s unbelievable that you did that.”
Jason shrugged. “You know, my job as a promoter doesn’t pay much, so I have to figure out how to eat at these locations and make ends meet. This is a reliable trick every time.
Sponsor? That’s exactly what Jason did during his summer holidays from high school. I found it incredible that he was still employed in the same position. “You’re continuing to promote?” I asked, trying not to speak too loudly.
“Yes, it’s not glamorous, but it pays the bills,” he said, oblivious to my growing discomfort.
Seeing my unease, he continued, “Don’t worry.” “Next time, it will be lot better. But you will have to pay because I took care of things tonight.
I pretended to laugh again while nodding. Indeed, Jason. I’m appreciative of tonight.
I would contact him as soon as I could, even though I knew I would never have the time. The cool, popular guy I used to look up to was still living the high school dream, turning to dubious means to make ends meet. On the drive home, I couldn’t stop laughing at how absurd it was all.
As soon as I took out my phone, I shook my head and blocked his number, surprised at how much a person could change and yet remain the same.
I felt rejuvenated and empowered when I woke up the next morning. I still couldn’t shake the events of the previous night, even though I had a whole day ahead of me. It felt amazing to realize how much I had grown and evolved since high school.
When I arrived at work, I couldn’t wait to tell my best friend and coworker Mia about the date.
As soon as I entered, she realized something wasn’t quite right. Emma, please supply the beans. “How did the big date go?
I let out a loud laugh. “Mia, you won’t believe it. Jason definitely put a hair in my dish and made a big deal out of not having to pay for our dinner.
Mia’s eyes widened in shock. “What action did he take? Are you for real?
I chuckled and followed along. “It feels like watching a bad movie.” The fact that I used to feel so strongly for him astounds me.
Mia shook her head and laughed as well. “Well, at least you got a free dinner out of it. And a great story to tell.
When I realized how true that was, I smiled. Yes, and it’s a valuable lesson. Sometimes the people we look up to as kids turn out to be very different from what we had imagined.
Mia laughed some more and leaned back in her chair. You managed to avoid a gunshot there. Is dating someone who thinks that kind of behavior is appropriate possible for you?
I shook my head, feeling more confident in my choices. “No, I’m not able to. All I’m asking for is gratitude for the chance. It gave me evidence of my development and advancement since high school.
For the rest of the day, I was absorbed in my job, but I couldn’t help but notice how much had changed. Even as a high school student, I could never have pictured myself where I am now, and seeing that Jason was stuck in the past only increased my gratitude for my journey.
Later that evening, when I relaxed with a glass of wine on my couch, I experienced a sense of closure. My crush on Jason had been a major part of my high school experience, but it was no longer controlling me.
I was free to enjoy the here and now and felt secure in the person I had become. I smiled to myself, excited to return to my story, chapter by chapter.
