My High School Crush Invited Me on a Restaurant Date Years Later, but I Was Speechless When It Was Time to Pay the Bill

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.

Meeting up with my high school love interest, Jason, again at a fancy restaurant felt like a scene from a romantic comedy. But as his endearing façade gave way to a shocking secret that hit me like a tonne of bricks, the evening took a gloomy turn. The boy I’d looked up to was gone, and in his place was someone I hardly knew.

Hello to all of you. I’m Emma, and I’m thirty-five years old. My background dates all the way back to my high school years. I used to be the quiet, scholarly girl who preferred to hang out at the library over parties. The golden boy of the school, Jason, had a major crush on me. Jason had it all—beautiful, well-liked, and seemingly endless.

When I saw Jason walking about, my best friend Sarah would prod me, saying, “Emma, come on, you have to at least try talking to him.”

I used to hide behind my big spectacles and blush hysterically. “You know he’s not in my league, Sarah. I am simply myself.”

“Emma, you’re incredible. She would argue, “He’d be lucky to know you,” but I would just shake my head.

Surrounded by his companions, Jason never once looked my way. Being the football team’s main player, he was always the centre of attention. From a distance, I observed, certain that he was unaware of my existence.


I never thought he would notice me with my braces and glasses. Furthermore, he never did. We lived in quite different worlds.

I had grown into a beautiful, accomplished woman years later. I exchanged my nerdy clothes for a chic look, my glasses for contacts, and my braces for a flawless grin. I was enjoying my best life, having developed a successful profession in marketing.

I recognised a voice from the grocery store one evening when I was choosing avocados.

I spun around to face Jason, who was still quite attractive despite appearing a little older. He was looking at me, astonished. He remarked, “Wow, you look amazing,” with wide eyes.

“Jonathan? Hello! It’s been a while,” I answered, my heart pounding.

He grinned broadly. Yes, it has, in fact. “How are you doing?”

We caught up on each other’s life over a long conversation. I told him about my recent return to the area and about my profession.

You’re in marketing now, then? That’s impressive,” nodded Jason.


“And you?” Curious about his life after high school, I asked.

Laughing, he said, “My work is interesting, but it’s not as glamorous as marketing,” effectively sidestepping my inquiry. What made him do that? While I was still digesting his answer, he surprised me by making an unexpected offer.

“Hey, how about we get together for dinner sometime? You know, appropriately catch up?”

Without hesitation, I agreed. Jason was the one! And he was sending me a date invitation! Naturally, I replied “yes.”


We got together at a classy downtown restaurant a few days later. I was impressed by his choice of restaurant; it was a classy establishment with excellent food. While we were placing our orders, Jason started talking about our time in high school.

“Do you recall when we were the football champions? “Man, those were the good old days,” he chuckled. “I still spend time with the team’s guys. We meet once a month as part of a small custom.”


Even while I listened courteously, I couldn’t help but feel a little disengaged. Jason seemed to be living in the past, but I had moved on from high school.

I forced a smile and said, “That sounds nice.” “Do you ever catch up with anyone else from school?”

“Not really,” he said with a shrug. “Only the men. And you, what say? Do you have any treasured high school memories?

I said, “Well,” not sure what to say, “I spend much of my time in the library. There aren’t many noteworthy stories there.”

He chuckled. “I recall that you were constantly buried in a book. Funny how things change, isn’t that right?

As our dinner arrived, we carried on our conversation. As Jason’s stories got monotonous, I saw that I was nodding off. When dessert arrived, I excused myself to use the bathroom.


When I got back, I saw Jason tinkering with something on my plate. He looked up with a naughty grin before I could ask him what he was doing.

He murmured, “Watch this,” and put a hair on my dish. “I’m going to show you a trick.”

As my eyes grew wide with shock, Jason beckoned the waitress over before I could object.

“I apologise, but there seems to be a hair in my friend’s food,” he exclaimed in a loud enough tone to draw attention. “This is unacceptable!”

The waitress apologised a lot and appeared upset. She said she would bring us new dishes and take the old one back. But Jason maintained that because of the inconvenience, we shouldn’t have to pay for the meals.

Following some back and forth, the manager finally arrived and consented to reimburse us for our dinners, along with a complimentary dessert.

Jason had a huge smile on his face as we left the restaurant. “You know how you deal with these locations. A negative experience should never have to be compensated for.”


I forced a smile, my head still spinning from the previous events. “I CAN’T BELIEVE you did that.”

Jason gave a shrug. “You know, I have to find ways to eat at these places and make ends meet because my job as a promoter doesn’t pay much. This trick is always effective.”

Sponsor? Jason spent his high school summer breaks doing just that. It was astounding to me that he continued to work at the same job. “You’re still promoting?” I asked, attempting to maintain a steady tone.

“Yes, it’s not glamorous, but it pays the bills,” he remarked, disregarding my mounting unease.

“Don’t worry,” he said, perceiving my discomfort. “It will be much better the next time. However, because I took care of things tonight, you will have to pay.”

I nodded and feigned another laugh. Yes, Jason. I’m grateful for tonight.”

I promised to give him a call as soon as possible, even though I knew I would never be able to. The cool, popular person I used to look up to was still living out of his glory days in high school, using shady tactics to get by. I couldn’t quit giggling at how ridiculous that was all on the way home.


I shook my head and banned his number as soon as I took out my phone, amazed at how much a person could change and still stay the same.

I awoke the following morning with a sense of empowerment and renewal. Even though I had a full day ahead of me, the events of the night before continued to consume me. Seeing how much I had changed and matured since high school made me feel good.

I was eager to inform my coworker and close friend Mia about the date when I got to my office.

She sensed something was off as soon as I stepped in. “Emma, provide the beans. “How was the big date?

I laughed out loud. “You won’t believe it, Mia. In order to avoid having to pay for our dinner, Jason really stuck a hair in my dish and made a fuss.”

Mia’s stunned eyes grew wider. “What did he do? Are you really real?”

I laughed, nodding along. “It like seeing a subpar film. It amazes me that I ever harboured such strong feelings for him.”

Mia laughed too and shook her head. “Well, at least it resulted in a free dinner for you. And a nice tale to narrate.”

I grinned when I realised how accurate that was. Indeed, and a worthwhile lesson. The persons we look up to as children can occasionally turn out to be completely different from our expectations.”

Still laughing, Mia sat back in her chair. “There, you escaped a bullet. Is it possible for you to date someone who believes that kind of behaviour is appropriate?

I shook my head, now more assured of my decisions. “I’m not able to, no. I’m just appreciative of the opportunity. It demonstrated to me my growth and progress since high school.”

I lost myself in my work for the remainder of the day, but I couldn’t help but notice how much had changed. I would never have imagined being where I am now, even in high school, and realising that Jason was trapped in the past made me even more grateful for my path.

I felt a feeling of closure later that night as I unwinded with a glass of wine on my couch. Though it had played a big role in my high school years, my crush on Jason was no longer able to control me.

I felt confident in who I had become and was free to appreciate the present and the future. I grinned to myself, eager to get back to work on my narrative, chapter by chapter.

Still in the mood for a fantastic book? Another bonus for you is this: Jen relives her childhood trauma when she matches on a dating service with her high school bully. She nevertheless goes on the date in an attempt to get retribution for the way she was handled. When the date doesn’t work out and Jen doesn’t get what she was hoping for, she sets up another meeting.

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