My High School Crush Invited Me on a Restaurant Date Years Later, but I Was Speechless When It Was Time to Pay the Bill
I’m Emma, 35, and my high school crush on Jason—the golden-boy quarterback—felt like a rom-com reunion when we bumped into each other at the grocery store. I’d transformed from a shy, bespectacled bookworm into a confident marketing exec; he still looked handsome but dodged questions about his life. He invited me to dinner at a swanky downtown spot, and I said yes.
Over appetizers, Jason relived football glory days and monthly bro meetups. I smiled politely, already sensing he hadn’t moved on. When I excused myself to the restroom, I returned to find him grinning mischievously, placing a hair on my plate. “Watch this,” he whispered. He loudly complained to the waitress, demanding comped meals. The manager caved—free food, free dessert.
Walking out, Jason boasted, “Promoter pay sucks, so I pull tricks to eat fancy.” He was still hawking flyers, same summer gig from senior year, and expected me to cover next time. I laughed it off, blocked his number in the car, and marveled at the absurdity.
Next day, I told my colleague Mia. We howled—dodged a bullet, scored a free meal, and closed a teenage chapter. Jason remained frozen in 2008; I’d outgrown him entirely. Glass of wine in hand that night, I toasted my growth and turned the page.
