85-year-old Whitefish Bay man takes trip to meet first-grade crush

WHITEFISH BAY (WITI) — 85-year-old Jerry Hill of Whitefish Bay recently took a little trip to catch up with his first grade crush — a girl who disappeared way back when he was five or six years old!

“She was the love of my life. I had a terrible crush on her,” Hill said.

She was a girl who made first grade bearable, before she disappeared — allegedly to Alaska.

“My major concern is how am I going to get to Alaska so I can go to school,” Hill said.

When Hill found out his first grade crush was still alive, he convinced his son to drive him to Elroy, Wisconsin. With his dog Finley Rose along for the drive, the widowed father of four set out to reunite with a woman he hadn’t seen since FDR was president!

Hill remembered so much about Gladys, but Gladys left, and life went on as it always does. The boy became a man, served in World War II, married, moved and multiplied, but never quite got over Gladys.

As the crush caravan rolled into Elroy, it stopped at the place Hill first and last saw Gladys — the Knickerbocker School just outside of town, abandoned, neglected and losing its fight with time.

Gladys was Hill’s first grade crush, but she was also his teacher! It just so happened, Hill was visiting Gladys on her 105th birthday!

When Hill arrived at the nursing home in Elroy and once again met Gladys, he remembered why he liked her so much as a teacher — she doesn’t forget a thing! Gladys even told Hill he wasn’t the only boy with a crush on her back in the day!

The reunion 80 years in the making lasted just a morning, as Gladys’ family was waiting to celebrate her birthday.

When all was said and done, Hill said he was happy for the reunion, and that the wait was worth it. He says the lesson he wants everyone to take from his story is that it’s never too late to reconnect with anyone.

“Wonderful. Absolutely wonderful. Words can’t describe it,” Hill said.

Hill and Gladys plan to spend a little more time catching up this summer.

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