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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 Was Speechless

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 faรงade gave way to a shocking secret that hit me like a ton of bricks, the evening took a gloomy turn. The boy Iโ€™d looked up to was gone, and in his place was someone I hardly knew.

Hello to all of you. Iโ€™m Emma, and Iโ€™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 allโ€”beautiful, well-liked, and seemingly endless.

When I saw Jason walking about, my best friend Sarah would prod me, saying,ย โ€œEmma, come on, you have to at least try talking to him.โ€

I used to hide behind my big spectacles and blush hysterically.ย โ€œYou know heโ€™s not in my league, Sarah. I am simply myself.โ€

โ€œEmma, youโ€™re incredible.โ€ย She would argue,ย โ€œHeโ€™d be lucky to know you,โ€ย but I would just shake my head.

Source: Midjourney

Jason never once turned to look at me while he was with his friends. Being the football teamโ€™s best player, he was always the center 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.

Source: Midjourney

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

โ€œEmma? Is that you?โ€

I spun around to face Jason, who was still quite attractive despite appearing a little older. He was looking at me, astonished. He remarked,ย โ€œWow, you look amazing,โ€ย with wide eyes.

โ€œJonathan? Hello! Itโ€™s been a while,โ€ย I answered, my heart pounding.

Source: Midjourney

He grinned broadly. Yes, it has, in fact.ย โ€œHow are you doing?โ€

We caught up on each otherโ€™s lives over a long conversation. I told him about my recent return to the area and about my profession.

โ€œYouโ€™re in marketing now, then? Thatโ€™s impressive,โ€ย nodded Jason.

โ€œAnd you?โ€ย Curious about his life after high school, I asked.

Laughing, he said,ย โ€œMy work is interesting, but itโ€™s not as glamorous as marketing,โ€ย effectively sidestepping my inquiry. What made him do that? While I was still digesting his answer, he surprised me by making an unexpected offer.

Source: Midjourney

โ€œHey, how about we get together for dinner sometime? You know, appropriately catch up?โ€

Without hesitation, I agreed. Jason was the one! And he was sending me a date invitation! Naturally, I repliedย โ€œyes.โ€

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.

โ€œDo you recall when we were the football champions? Man, those were the good old days,โ€ย he chuckled.ย โ€œI still spend time with the teamโ€™s guys. We meet once a month as part of a small custom.โ€

Even while I listened courteously, I couldnโ€™t help but feel a little disengaged. Jason seemed to be living in the past, but I had moved on from high school.

Source: Midjourney

I forced a smile and said,ย โ€œThat sounds nice.โ€ โ€œDo you ever catch up with anyone else from school?โ€

โ€œNot really,โ€ย he said with a shrug.ย โ€œOnly the men. And you, what say? Do you have any treasured high school memories?โ€

I said,ย โ€œWell,โ€ย not sure what to say,ย โ€œI spend much of my time in the library. There arenโ€™t many noteworthy stories there.โ€

He chuckled.ย โ€œI recall that you were constantly buried in a book. Funny how things change, isnโ€™t that right?โ€

Source: Midjourney

As our dinner arrived, we carried on our conversation. As Jasonโ€™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,ย โ€œWatch this,โ€ย and put a hair on my dish.ย โ€œIโ€™m going to show you a trick.โ€

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

โ€œI apologize, but there seems to be a hair in my friendโ€™s food,โ€ย he exclaimed in a loud enough tone to draw attention.ย โ€œThis is unacceptable!โ€

The waitress apologized a lot and was upset. She said she would bring us new dishes and take the old one back. But because of the inconvenience, Jason claimed that we shouldnโ€™t have to pay for the meals.

Source: Midjourney

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.ย โ€œYou know how you deal with these locations. A negative experience should never have to be compensated for.โ€

I forced a smile, my head still spinning from the previous events.ย โ€œI CANโ€™T BELIEVE you did that.โ€

Jason gave a shrug.ย โ€œYou know, I have to find ways to eat at these places and make ends meet because my job as a promoter doesnโ€™t pay much. This trick is always effective.โ€

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.ย โ€œYouโ€™re still promoting?โ€ย I asked, attempting to maintain a steady tone.

Source: Midjourney

โ€œYes, itโ€™s not glamorous, but it pays the bills,โ€ย he remarked, disregarding my mounting unease.

โ€œDonโ€™t worry,โ€ย he said, perceiving my discomfort.ย โ€œIt will be much better the next time. However, because I took care of things tonight, you will have to pay.โ€

I nodded and feigned another laugh.ย โ€œYes, Jason. Iโ€™m grateful for tonight.โ€

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 couldnโ€™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.

Source: Midjourney
Source: Midjourney

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.

Source: Midjourney

She sensed something was off as soon as I stepped in.ย โ€œEmma, provide the beans. How was the big date?โ€

I laughed out loud.ย โ€œYou wonโ€™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.โ€

Miaโ€™s stunned eyes grew wider.ย โ€œWhat did he do? Are you really real?โ€

Source: Midjourney

I laughed, nodding along.ย โ€œItโ€™s like seeing a subpar film. It amazes me that I once harbored such strong feelings for him.โ€

Mia laughed too and shook her head.ย โ€œWell, at least it resulted in a free dinner for you. And a nice tale to narrate.โ€

โ€œI grinned as I realized 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.โ€

Source: Midjourney

Still laughing, Mia sat back in her chair.ย โ€œThere, you escaped a bullet. Is it possible for you to date someone who believes that kind of behavior is appropriate?โ€

I shook my head, now more assured of my decisions.ย โ€œIโ€™m not able to, no. Iโ€™m just appreciative of the opportunity. It demonstrated to me my growth and progress since high school.โ€

I lost myself in my work for the remainder of the day, but I couldnโ€™t help but notice how much had changed. I would never have imagined being where I am now, even in high school, and realizing that Jason was trapped in the past made me even more grateful for my journey.

Source: Midjourney

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.

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