Chapter 5: Old Flames and Bitter Lessons

Lillian and I went to Silver Hollow High, though we weren’t in the same class. She was the student council type, always clutching books, while I was the guy in the letterman jacket, living for homecoming games and cafeteria pizza. Our circles overlapped just enough for sparks to fly.

When I chased her senior year, it didn’t take much. I was the star athlete, the guy every parent wanted their daughter to date. Friday night games, SAT prep classes, tailgate parties—I was in my element, untouchable.

Not only did I kill it in basketball, but I always took first in the sprints and long-distance at track meets. My name was in the local paper, my photo on the bulletin board. Even teachers would high-five me in the hallway.

The day Lillian agreed to date me, rumor had it a couple freshmen skipped homeroom to mope in the bleachers. I wore it like a badge of honor.

But after the SATs, I realized she was all about status. She talked about colleges with $50k tuitions like it was nothing, never caring about scholarships or loans—just the label. She dreamed of a finance major, picturing herself living in a Manhattan high-rise.

I tried to warn her—finance was for trust fund kids, not people like us. She called me a pessimist, said I lacked ambition. “I’m a girl, getting married is the most important thing in life. Didn’t you say everyone in finance is rich? I’ll just pick one carefully and after graduation, why would I need to work?”

Her words echoed in my head for days. I started wondering if I’d ever really mattered to her. She never cared that I knew her true thoughts. We fought all summer, and every time, she’d threaten to break up. But I couldn’t let go—she was my first love.

I thought love was supposed to be passionate, and if you broke up, it should only be for unavoidable reasons. How could we break up just because I was broke?

So, even though she brought up breaking up countless times, I never agreed. I even changed my major and enrolled at her college, convincing myself it was worth it.

But she started dismissing me, calling me "just some loser who’s obsessed with me" in front of her friends. Then she started dating a rich guy from our department—he drove a black Audi, while I was struggling to buy a used bike.

Every time I saw them, I wanted to slash his tires. But all I ever did was clench my fists and walk away, telling myself, “Where there’s life, there’s hope.”

It turned out patience brought a turnaround. That guy dumped her after three months. She showed up at my door in the rain, mascara streaked, looking lost. I took her back, gave her everything—asked my parents for extra money just to spoil her, even as guilt gnawed at me.

But less than half a year later, she left again—for another guy with connections. I wasn’t worried; he was a player. Sure enough, he dumped her in two months. She came back to me, and we started the cycle again.

After that, I stopped getting my hopes up. Throughout college, we broke up and got back together seven times, but on graduation day, she was still my girlfriend.

After graduation, my parents sold everything to get me a job as a middle school PE teacher back in Silver Hollow. Lillian couldn’t find work either, so she came home too. I worked day and night to save for a house and marry her.

But she left again—this time for a rich guy from Colorado she met online. I thought it’d be like before, but then I saw her wedding photos on Facebook. She blocked me, disappeared from my world, and became a rich lady at last.

I was heartbroken—lost my job, thought about ending my life more than once. I’d walk out to the bridge over the river, thinking maybe I’d just jump. But I never did.

One day, on the bridge, two cars collided behind me. A white car caught fire, a girl trapped inside. Everyone stood back, filming. I thought, if I was going to die anyway, why not go out saving someone? I ran in, pulled her out just before the flames hit.

That girl was Natalie.

Even with her face blackened by smoke, I felt drawn to her. She was small but her eyes sparkled—like a comic book heroine. She started pursuing me, bringing cookies to the hospital, leaving notes on my windshield. No one had ever chased me before.

When I learned her family was wealthy, I agreed to date her. Less than a year later, we married. Her parents handed me the rent spreadsheet and keys—I became the guy who collected envelopes of cash around town, the one everyone envied.

Within three years, we saved over $450,000. Life was good—Netflix nights, weekend trips, designer gifts, even gift cards for my parents. I imagined us growing old together, but told myself if I just endured the pregnancy, it’d all go back to normal.

But fate had other plans. The day Lillian walked back into my life at the stroller store, everything started to wobble. She looked worn down, her old class ring glinting on her finger. Suddenly, I wanted to show her how far I’d come.