“Jenna, this is urgent!” my 66-year-old mother exclaimed in a voicemail I discovered outside my office. After she called me five times in quick succession, I knew I had to step out to listen. My heart sank as I thought about her living situation with my 92-year-old grandmother, who had been experiencing frequent falls.
“A guy from Match-dot-com messaged me!” my mom’s excited voice continued. “I’m so confused about what to say!”
As a freelance writer for e-Cyrano.com, where I crafted online dating profiles for clients, particularly Baby Boomers, I figured that if they could navigate online dating, so could my mom. What I didn’t anticipate were the constant emergency calls. “He said I’m beautiful and charming,” my mom gushed when I returned her call. “Then he sent a cute cartoon rose! Can you believe someone called me beautiful again?”
While I wanted to remind her that he likely sent similar messages to several women, I was thrilled she was stepping outside her comfort zone. My mom had always struggled with technology, and online dating was a whole new ballgame for her. From her clumsy username choice, “Delusins” (which led one suitor to question her sanity), to nearly wiring $1,000 to a clear scammer, she was a novice. To top it off, her grandmother’s nurse suggested she post swimsuit photos—definitely not her style. I jumped in to coach her on how to navigate the online dating world: spotting generic messages, avoiding the pen-pal trap, and choosing appropriate photos (like a close-up, a medium shot, and one from further away—no swimsuits!).
A 65-year-old client once said, “If dating is tough at your age, imagine how hard it is for your mom!” I reflected on my mom’s life since her second divorce when I was just 9. Although she had her share of boyfriends through work or friends, she had recently retired, and most of her friends were in couples. My grandmother was her only constant companion, and most of her phone calls were about doctors or Medicare rather than potential dates.
While my mom didn’t necessarily need to date, I was glad she was trying. With my grandma’s health declining and assisted living on the horizon, I thought a little romance might distract her from the heaviness of her situation. After all, it would be nice for her to have someone to share dinner with or go to a movie instead of just talking about her mother’s health.
“Jenna, what should I say back?” my mom asked during another call.
“He mentioned he plays golf,” I suggested. “Ask him about his handicap.”
Her response? “My daughter told me to ask you about your handicap.” Oh, Mom! I reminded her to rephrase it in her own style so he wouldn’t think I was the one interested. It was a nostalgic moment, reminiscent of her checking over my school assignments. “Every word matters,” she’d say, and I found myself echoing that sentiment as we crafted thoughtful replies to her online suitor.
One day, she called me, practically squealing, “He wants to meet in person!” I was thrilled for her, feeling like I was the one going on a date. I quickly turned into an overprotective parent, advising her on what to wear (feminine yet modest) and emphasizing the importance of meeting in a public space. I reminded her to tell a friend where she was going, set a time limit, and have an exit strategy if things went south—just like she had told me when I was dating in high school.
After her dates, she would call me to recap, often saying, “Jenna, it was terrible!” but occasionally, I’d hear, “Jenna, I think I’m in love!” While I didn’t pry for every detail, it was fascinating to hear snippets about where they went, if they were gentlemen, and how they interacted. I began to realize that men in their 60s could be just as romantic as those in my own age group, but they could also be just as inappropriate. As I found myself saying things like, “You don’t need to kiss him,” “He’s not the one,” and “Don’t settle,” I recognized I needed to heed my own advice.
A few months later, my grandmother moved into assisted living, and now my mom brings her new boyfriend along for visits.
This journey has been unexpected for both of us, but it has sparked a new chapter in my mom’s life.
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Summary:
In this heartwarming tale, Jenna finds herself unexpectedly coaching her mother through the world of online dating after her mom receives a message from a suitor. Despite her mother’s initial lack of tech-savviness, Jenna helps her navigate the ups and downs of dating life, offering guidance on communication, safety, and self-discovery. Their journey not only brings joy and excitement but also helps address the challenges of impending changes in their family dynamic.