By: Jessica Green
“Jess, it’s urgent!” My 66-year-old mother’s voice blared from my voicemail as I stepped out of my office for a breather. After five ringing calls, I knew something was up. I braced myself for the worst, considering she lived with my 92-year-old grandmother, who had been experiencing frequent falls lately. “A guy from Match-dot-com reached out to me!” she continued in a cheerful tone. “Call me back! I’m lost on how to respond!”
As a freelance writer with experience crafting online dating profiles for e-Cyrano.com, I figured if my clients in the Baby Boomer demographic could navigate the digital dating world, so could she. What I didn’t anticipate were her frantic late-night calls. “He wrote that he finds me beautiful and charming,” my mom gushed when I returned her call. “And he sent me a picture of a rose! It’s adorable and looks like a cartoon. He called me ‘beautiful,’ Jess! Can you believe it’s been so long since someone said that to me?”
While I wanted to remind her that flattery like that is often a cookie-cutter approach in online dating, I was thrilled she was stepping out of her comfort zone. My mom was not the most tech-savvy person, and the online dating scene was like a foreign land to her. From picking a username (she chose a quirky mashup of her first and last name, “deluvette,” which led one guy to ask if she was deluded!) to almost sending $1,000 to a clear scammer, she was on a steep learning curve. One time, her grandmother’s nurse suggested posting swimsuit photos—definitely not her style—so I had to step in and offer some guidance on how to navigate the world of online dating: spotting cut-and-paste messages, avoiding the pen pal trap, and selecting some tasteful pictures (a close-up, a mid-range shot, and a full-body photo, but absolutely no swimsuit images).
One day, a 65-year-old client of mine said, “If you think dating is tough at your age, imagine how it is for your mom.” I reflected on how my mom had lived with her mother since her second divorce when I was just nine years old. Occasionally, she’d have boyfriends from work or social circles, but now that she was retired and her friends were settled, her social life had dwindled. Most of her phone calls were from Medicare representatives or doctors, not potential suitors.
Although dating wasn’t a necessity for my mom, it felt important. With my grandmother likely needing assisted living soon, I thought it was great that my mom was seeking companionship. It would be a welcome distraction from the heaviness of their situation—my grandmother’s falls and the ever-present discussions about her health. Having someone to share outings with, like movies or dinners, could lift her spirits.
“Jess, how do I reply?” she asked during yet another call.
“He mentioned he plays golf,” I suggested. “Ask him about his handicap.”
She shot back an email that read, “My daughter says 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 in him. It was like a role reversal from when she’d check my homework, stressing that “every word matters.” I told her the same as we crafted a thoughtful reply, ensuring we addressed his email and profile details.
Then came the day when she called, practically squealing, “Jess, he wants to meet in person!” I felt as excited as if I were going on the date myself, but also like an overprotective parent, sending her into the unpredictable waters of dating. I advised her on what to wear (something feminine yet modest), to meet in a public space, let a friend know her whereabouts, set a time limit, and have an exit strategy if things went south. I reminded her to channel the same “just say no” advice she’d given me two decades ago.
After her dates, she would often call to recap, usually saying, “Jess, it was horrible!” with the occasional “Jess, I think I’m in love!” I didn’t pry for every detail, but it was fascinating to hear snippets—whether he was a gentleman, if he paid, and what common interests they shared. I realized that men in their 60s could be just as romantic as those in their 30s and 40s. They would bring actual roses, not just cartoon ones, and show respect. However, there were also some who left much to be desired—too forward, lacking manners. As I found myself advising, “Don’t feel pressured to kiss him,” and “Nope, not the right match,” I recognized that I needed to heed my own advice.
A few months later, my grandmother moved into assisted living, and my mom began bringing her new boyfriend along for visits.
In summary, becoming an online dating coach for my mom was a wild ride filled with surprises and lessons for both of us. While it was challenging to navigate the dating scene, it ultimately brought her joy and companionship in a time when she needed it the most.
Keyphrase: Online dating for seniors
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