The Villages - May 2017 - 41
High School Sweethearts
Judy (Brenner) and Roy Dugan
Wooster High School, Wooster, Ohio
People come and go. But
sometimes, they come again.
Judy and Roy's paths were
wound that way - intersecting
and weaving throughout the years.
They shared a seventh-grade
homeroom in Wooster, Ohio.
"He invited me to a dance and we ended up dating all throughout high school," Judy
recalled. After high school, the two went on to separate colleges and parted for a time. Later, they got engaged
when he decided to join the Air Force.
"My parents didn't think we could make it," Judy said,
"and so they suggested I give the ring back."
Judy complied, agreeing that four years was a long
time to wait for Roy to return.
After his stint in the Air Force, Roy got married and
"I thought that was it," Judy said. "I never imagined
we'd end up together after that, although I hoped we
In 1961, their paths crossed again and a new chance
at love emerged. The couple was married in 1962.
"His children became my
family," Judy said. "We opened a
garden center and landscaping
business and worked hard until
we sold the company in 2001."
Judy and Roy traveled a bit, from
Ohio to Alaska, and began making
plans for a sunny retirement in the South.
"We weren't exactly sure where we would
settle," Judy said.
In 2002, they landed in The Villages and bought a
place in the Village of Woodbury soon after. These days
they play golf and mah-jongg. Roy still likes the feel of
damp earth on his hands, and spends warm days working in the garden. Together they stay active, reminisce
about their high school days and cherish the path that
led them back to one another again.