In 1984, Andrew Gottlieb penned a note so long that it covered two pages of Elizabeth Alexandra Steuart Osha’s high school yearbook. In it, he matter-of-factly stated that they would one day get married. Four decades later his prediction came true.

The two met in seventh grade. Ms. Osha, who goes by Steuart, had transferred to the Dalton School on Manhattan’s Upper East Side. In what Mr. Gottlieb described as his “first suave move ever,” he asked the new girl if she’d go out with him. He treated Ms. Osha to a soda at a deli.

“As far as I knew, that was it, that’s what ‘going out’ was,” Mr. Gottlieb said. “I felt I had fulfilled my obligations.”

Mr. Gottlieb and Ms. Osha, now both 58, maintained a cordial relationship and were in the same social circles throughout the rest of their school years. They became close friends in the year or two before graduation.

“I was crazy about her,” he said. “But Steuart only liked me as a friend.”

[Click here to binge read this week’s featured couples.]

Both fondly recall evenings spent at Mr. Gottlieb’s apartment in Manhattan, where both grew up, watching television. One of their favorite shows was “Moonlighting,” starring Cybill Shepherd and Bruce Willis, which, amusingly, had a will-they-or-won’t-they plot hook.