The Time I Became an Online Dating Consultant for My Mother

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“Julia, we have a situation,” my 66-year-old mother’s voice blared through my voicemail as I stepped outside my office. After receiving five consecutive calls, I knew this was urgent, so I took a break from work to listen. My anxiety heightened as I recalled that she lived with my 92-year-old grandmother, who was more of a maternal figure to me than my mom. Grandma had been having frequent falls lately. “A guy from a dating site messaged me!” my mom continued in her message. “Call me! I have no idea what to say back!”

As a freelance writer for e-Cyrano.com, I had experience crafting online dating profiles, and I knew many clients in my mom’s demographic—Baby Boomers. If they could navigate online dating, surely she could too. However, I didn’t anticipate the barrage of emergency calls at all hours. When I called her back, she excitedly recounted, “He said I’m beautiful and charming!” She mentioned a cartoonish rose emoji he included. I felt a mix of joy and concern for her; while it was thrilling to hear her excitement, I wanted to gently remind her that such compliments were often generic and likely sent to multiple women. Still, I was thrilled to see my mom stepping outside her comfort zone.

Technologically challenged, she struggled with every aspect of online dating—from selecting a username (she chose a combination of her first and last name, “delujoy,” which led one man to jokingly ask if she was delusional) to nearly wiring $1,000 to an apparent scammer. One time, a nurse suggested she post swimsuit photos, which was completely out of character for her. I had to step in and guide her on the essentials of online dating: how to spot copy-paste messages, avoid becoming pen pals, and post appropriate photos (a close-up, a medium shot, and a full-body picture—definitely no swimsuit shots).

One of my clients, a 65-year-old man, once said, “If you think dating is challenging for someone your age, try it at your mom’s age; I can tell you it’s not easy.” My mom had lived with grandma since my parents’ divorce when I was nine. Though she occasionally dated men she met through work or friends, most of her social circles were now coupled up since her retirement. Grandma had become her mainstay, and the only calls she received were usually from medical professionals, not eligible bachelors.

While my mother didn’t strictly need to seek love online, I was relieved she was trying, especially with the impending transition of my grandmother into assisted living. I felt it would provide my mom with a welcome distraction from the heavy realities of caring for her aging mother. Having someone to share experiences with—movies, dinners, and outings—would break up the monotony of phone calls about healthcare plans.

“Julia, what should I say in response?” she asked during another call. “He mentioned golfing.” I advised her to ask about his handicap. In her excitement, she wrote, “My daughter suggested I ask you about your handicap.” “Mother!” I exclaimed, urging her to rephrase it in her own voice to avoid the impression that I was the one interested in him. It reminded me of my childhood when she would meticulously review my homework. “Each word matters,” she used to say, and I echoed that sentiment as we crafted a thoughtful response to her suitor, making sure it reflected genuine interest in his profile.

One evening, she called, practically squealing, “He wants to meet in person!” My heart raced as if I were the one going on a date. I felt like an overprotective parent, sending her into the unpredictable world of dating. I advised her on appropriate attire (feminine yet modest) and emphasized safety: meet in a public space, inform a friend of her whereabouts, set a time limit, and have an escape plan if things went awry. I recalled the advice she had given me two decades ago when I began my own dating journey.

After each date, she would call to share her experiences, often stating, “Julia, it was terrible!” — although occasionally, it was followed by, “Julia, I think I’m in love!” I didn’t pry for every detail, but I found it fascinating to hear about her outings, whether he was a gentleman, if he paid, and what interests they shared. I realized that some men in their 60s could be just as romantic as those in their 30s and 40s, offering real roses instead of cartoon emojis and displaying respectful behavior. Yet, some were inappropriate, too forward, or just plain rude. As I found myself repeating things like, “You don’t have to kiss him,” “He’s not the right match,” and “Don’t settle,” I recognized that I, too, needed to heed this advice.

A few months into her online dating journey, my grandmother transitioned to an assisted living facility. Now, my mom brings her boyfriend along during visits, a testament to the joy and companionship that can bloom at any age.

In conclusion, guiding my mother through the landscape of online dating not only helped her find companionship but also deepened our bond. It was a journey of rediscovery for both of us, filled with laughter, lessons, and a reminder that love knows no boundaries.

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