A Love That Stood the Test of Time

The first time Tim Holly laid eyes on Dorothy "Dot" Holbrook, it was the first night of their freshman year at Kentucky Wesleyan College. The school held a mixer for incoming students, and Dot, drawn to intellectual men, spotted Tim sitting on a piano bench, glasses perched on his nose.

"He looked very intelligent," she recalls with a laugh. "I didn’t know whether he actually was, but the glasses made him look that way, so I walked over and introduced myself."

Tim, immediately intrigued, asked her to join him for coffee after the event. And just like that, their story began.

For three months, they were inseparable, dating exclusively but never quite labeling their relationship as serious. They were young, enjoying each other’s company without fully realizing what love was. Then, as quickly as it began, it ended. Dot, eager to experience college life and meet new people, broke things off.

"I was barely 18," she says. "I enjoyed dating Tim but also wanted to see other people. I didn’t think he was upset at the time. I didn’t know until 72 years later how much it really hurt him."

Tim put on a brave face. "I acted like it didn’t bother me," he admits, "but it did. It bothered me extremely."

A Love Rekindled

Life carried them in different directions. Both married, raised families, and built fulfilling lives. But fate, or perhaps perseverance, had other plans. More than seven decades after their college romance, Dot and Tim reconnected on Facebook.

"It was strange at first," Tim says. "I expected a warm response! But after we talked for a while, I started playing songs for her on my guitar. That had been ‘our thing’ in college."

As they reminisced, they found common ground in their values, their faith, and their love for music. The bond they once shared had not only survived but deepened with time.

In 2023, Tim made a trip to Kentucky for Thanksgiving and stopped in Owensboro to visit Dot. The moment he saw her, his old feelings rushed back.

"The attraction I had for her 74 years ago was immediately back," he says. "I asked if she would mind if I moved closer. The five-hour drive from Ohio once a month wasn’t working."

Dot agreed, and her children gave their blessing. Initially, they planned to live together, but life had one more curveball to throw their way. Tim suffered a stroke, making independent living impossible. That’s when Dot began searching for a place that could provide the care he needed while keeping them close.

"My daughter-in-law and I toured Cedarhurst," she says. "Tim was still in rehab in Ohio, so we FaceTimed him throughout the tour so he could see the apartment and the community."

Tim made his decision that very day.

"Andrea and I talked about an apartment near the dining room so I could get around easily, and we started making arrangements."

Love in the Present

Now, just minutes away from one another, their love story continues to unfold at Cedarhurst of Owensboro. Dot visits Tim three times a week, spending hours together talking, laughing, and, of course, making music.

"We always eat lunch together," she says. "Then we walk the hallways to get our exercise. We hold each other accountable for that. We love sitting by the fireplace in the Four Seasons room. And sometimes, we just go back to Tim’s apartment, prop our feet up, and take a nap."

Their families have embraced their rekindled romance, and while marriage isn’t in the plans, their love is as strong as ever.

"I wasn’t sure if my children would accept it," Dot admits. "Tim was married for 67 years, and I was married for 53. But when I asked them, they said, ‘Whatever makes you happy, Mom.’ And now, they’ve come to know Tim and are very fond of him."

Lessons in Love and Second Chances

Looking back, neither Tim nor Dot credits fate for their reunion.

"I don’t believe in fate," Dot says. "I wasn’t expecting a romantic relationship. I just thought it would be nice to see Tim again after all these years."

Tim, ever the realist, agrees. "I wouldn’t say it was fate. I’d say it was perseverance."

As for advice on love and second chances?

"You have to talk," Tim says. "Make sure you know what the other person believes, what they want, and that you’re compatible."

After 74 years apart, Tim and Dot have found their way back to each other. And whether it was fate, perseverance, or simply the enduring nature of true connection, one thing is certain: their love, like their music, is timeless.

 This story was originally published in the Spring 2025 issue of Flourish Magazine.

About the Author

Ryan Davis is the Corporate Communications Manager at Cedarhurst Senior Living and the writer behind every story in Flourish magazine. He holds a Communications degree from Indiana University and brings 19 years of experience to his role, which he began in January 2024. Ryan is passionate about storytelling, especially sharing the meaningful lives of Cedarhurst residents, families, and staff. He hopes each published story becomes a treasured legacy for loved ones.