Is Dating an Old Friend a Good Idea?

Health Writer
Medically Reviewed

If you sometimes have memories that pop up out of the blue about someone you dated decades ago—maybe a high-school crush or your first love from your college days—you have plenty of company.

Being hit with that random blast from the past also may make you wonder what would happen if you had a chance to reconnect with that person now, especially if you’re among the growing number of middle-aged and older Americans who are divorced, widowed, or otherwise single.

There’s a reason memories of those romantic relationships tend to recur over the years, even when you’ve spent most of your life with another person whom you’ve loved just as much or more. “Neurobiologically, loving someone leaves a mark, good or bad,” says Justin Garcia, Ph.D., an associate director at the Kinsey Institute for Research in Sex, Gender, and Reproduction at Indiana University. “But if the relationship occurred during the formative period of your life when you were building your sense of self and your sexual identity, the pull of those memories is even stronger.”

And while there are various ways you might cross paths with a love from long ago, living in today’s digital world increases the likelihood of that happening. “With the growing use of social media by people in this age group, we’re seeing more people who are actually getting back in touch and interacting with a former sweetheart,” Garcia says.

An email that changed everything

In fact, that’s exactly what sparked such a reunion for one suburban Chicago woman when she least expected it—at the age of 83. For seven years she had been living alone following the death of her husband, with whom she’d had two children and a happy 55-year marriage.

“I was living alone, but I had enough friends to enjoy a full life and I hadn’t even thought about dating,” says “Cathy,” who asked that we not use her real name to protect her privacy. “My relationship with my husband had been so good that I thought it was too high a bar for someone else to reach.”

But everything changed one day when she got an email from a man who’d been her first serious boyfriend in high school. She hadn’t heard from him since they parted ways after he decided to attend a university in California and ended up settling out there. Cathy opted to earn her degree at a college in Illinois, which is where she met her husband.

“Howard” (not his real name) was able to get back in touch with her because he spotted Cathy’s profile on the social networking site LinkedIn and invited her to connect. Cathy laughs when she recalls how she reacted to that first email from Howard: “I wrote back right away, and here’s what I said: “I’m so glad you’re alive. Most everyone else we knew is dead.”

Not only were they both still alive, but they also were sharp mentally, physically fit, and in good health overall. After communicating long-distance via phone and email for a couple of months, they decided to get together in person, meeting halfway in Phoenix.

“It was a rare and precious opportunity,” she says. “Not only did we ignite the romance of our youth, but over the next three years we had some wonderful adventures together, traveling to Utah, Yellowstone, and other beautiful parts of America I’d never seen.”

Howard sometimes came to Chicago to visit her, but it was Cathy who did most of the shuttling back and forth. Every three months or so she’d fly out to join him for three or four weeks of travel. “He had a luxurious motor home complete with a 1,000-book library that we’d travel in, so it was like being on a comfortable but still exciting vacation,” she says.

A light-bulb moment

But as time wore on she found it increasingly difficult to take off for weeks at a time. “I felt torn, because while I was with him, I started worrying about things that needed to be done at home, and when I was back, I’d be wondering how he was doing on his own.”

A turning point came when Cathy returned from one those trips as she was approaching her 86th birthday. She walked into her beloved home and found herself breathing a sigh of relief. “It finally hit me between the eyes. If I were in my 50s, maybe I could continue all of this traveling back and forth, but at my age, time is even more precious. I really wanted to spend as much of it as I could in the home I love, doing what’s really important to me.”

Cathy realized that while they both loved to read, in other ways she and Howard were quite different. What Howard loved most was being out in nature, surrounded by mountains. Cathy, however, preferred going to plays, seeing movies, or meeting friends for dinner in the city. “No matter how much I cared about Howard, I realized it was too much of a compromise for me to keep going back and forth to the other side of the country to live the life he loved.”

When Cathy called to explain how she was feeling, Howard said he understood completely and agreed that they should each maintain their individuality and live where they were happiest. Despite being far apart geographically, they remain very close. “I still love to talk with him and we actually chat on the phone every night,” she says. “But I also treasure having an independent life, which is something most women in my generation didn’t have when we were younger.”

Cathy’s unwillingness to compromise is actually one of the hallmarks of singles in their 50s and up, according to results of a recent survey released by Our Time, an online dating site for Baby Boomers. The poll found that 55 percent of the singles age 50 and up surveyed said they knew exactly what they wanted when it came to relationships. An even higher proportion—nearly 75 percent—said they knew what they didn’t want.

The bottom line

Getting back in touch with a special someone from your youth can be worthwhile, regardless of the ultimate outcome. “Reconnecting is an opportunity to explore your relationship at a different point in life,” says the Kinsey Institute’s Garcia, who is also an assistant professor of gender studies.

“For some it can lead to rekindling romantic love. Others may find they are taking care of unfinished business. But for many people they may find that it was best that they went their separate ways when they did," he says.