“Hey, Em, this is urgent!” my 66-year-old mother exclaimed in a voicemail I heard while stepping out of my office. After five calls in quick succession, I knew something was up. My heart raced as I wondered what the situation could be, particularly since she lived with my 92-year-old grandmother, who had been having a rough time with falls lately. “A guy from Match.com messaged me!” she continued, her excitement spilling over. “Call me! I don’t know how to respond!”
As a freelancer who helped people craft their online dating profiles at e-Cyrano.com, I had clients in my mom’s age group—the Baby Boomers. I thought, if they could navigate the world of digital dating, so could she. Little did I know, I’d be receiving panicked calls around the clock. “He said I’m beautiful and charming!” she gushed when I returned her call. “Then he sent a picture of a rose. It’s adorable, like a cartoon! Can you believe someone called me ‘beautiful’?”
While I wanted to remind her that he probably sent that same line to several women (the rose was cute, but still), I was thrilled she was stepping out of her comfort zone. My mom was barely tech-savvy, let alone skilled at online dating. From choosing a username (she combined her first and last names into “delusins,” which led to one guy asking if she was delusional) to almost sending $1,000 to someone who clearly was trying to scam her, she needed some serious guidance.
Then there was the time when my grandmother’s nurse suggested my mom post swimsuit photos online (not really her style). That’s when I stepped in and began coaching her on the dos and don’ts of online dating: recognizing generic messages, avoiding the “pen pal” trap, and posting modest photos (a close-up, a medium shot, and a full-body shot—absolutely no swimsuit pictures!).
One day, a 65-year-old client of mine said, “If dating is tough for you, imagine how it is for your mom!” I thought about my mom’s history; she had lived with my grandma since her second divorce when I was nine. Yes, she had a few boyfriends from work or friends, but now that she was retired and her friends were all in relationships, it was mostly her and grandma, who was a constant presence in her life. Most of her calls were from Medicare reps, not eligible bachelors.
While my mom didn’t necessarily need to date, I was glad she was trying. I think we both understood that with grandma likely moving into assisted living soon, my mom would be facing some lonely times ahead. Although she knew how to live as a single woman, dating could offer a much-needed distraction from the stress of frequent doctor visits and ambulance rides. Plus, having someone to join her for movies, dinners, and concerts would be a welcome change, especially instead of calls about healthcare.
“Em, what should I say back?” she asked during another call. “He mentioned playing golf.”
“Ask him about his handicap!” I suggested.
She then shot him an email: “My daughter said to ask you about your handicap.” Oh, Mom! I reminded her to use her own words so he wouldn’t think I was the one interested. It took me back to my childhood when she’d check my homework with the same meticulousness. “Every word counts,” she always said. With that in mind, we crafted a thoughtful response that showed she had read his email and his profile.
One evening, she called me, giddy as a schoolgirl: “Em, he wants to meet in person!” I was over the moon for her, but I also felt like a protective parent watching her venture into the unpredictable world of dating. I advised her on outfit choices (feminine yet modest), the importance of meeting in public, and to let a friend know where she was going. I reminded her to set a time limit and have a way out if things went south. “Just say no,” I echoed the advice she had given me years ago.
After their dates, she would call to share her experiences, usually saying, “Em, it was terrible!”—though occasionally I’d hear, “Em, I think I’m in love!” I didn’t always ask for the details, but I found it fascinating how some men in their 60s could be just as romantic as those in their 30s and 40s (showing up with real roses, not just cartoon ones, and standing when she excused herself). However, some of them were definitely not gentlemanly—too forward and overly familiar. I found myself saying things like, “You don’t have to kiss him,” or “Nope, he’s not the one for you,” and “Don’t settle.” It hit me that I should be taking this advice myself.
A few months into this adventure, my grandma did move into assisted living. Now, my mom brings her boyfriend along for visits. Who would’ve thought I’d end up as her online dating coach?
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In summary, navigating the world of online dating for my mom turned out to be an unexpected journey filled with surprises and lessons. From crafting messages to discussing date etiquette, I discovered that the dating game has its ups and downs, regardless of age. And as my mom embraced this new chapter in her life, it became a bonding experience for both of us.