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

Posted on November 17, 2025 By Maddie Hart No Comments on My High School Crush Invited Me on a Restaurant Date Years Later, but I Was Speechless When It Was Time to Pay the Bill

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I wasn’t planning on helping anyone that night. All I wanted was a quiet walk to clear my head after a long day filled with spreadsheets and deadlines. The city felt heavy in November, the kind of evening where you can almost hear the sidewalks sigh.

Halfway down Elm Street, something caught my eye — a figure standing alone on the rooftop of the old Carter Building. Still. Too still. A posture that made my heart skip for reasons I didn’t want to consider.

A man. Mid-thirties. Shoulders tense. Standing far too close to the edge.

I stopped. I should’ve called someone, but something pushed me forward instead. Maybe instinct. Maybe stubbornness.

The building was nearly empty, the elevator broken as always, so I climbed five flights of stairs and pushed the rooftop door open. Cold wind rushed out to greet me.

He didn’t turn around. Didn’t move at all.

“Hey,” I said gently, just loud enough to cut through the silence.

He let out a breath. “You shouldn’t be up here.”

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