The Time I Became an Online Dating Coach for My Mom

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“Hey, Jamie, we need to talk!” my 66-year-old mom’s voice blared through my voicemail as I was wrapping up a busy workday. After she called me five times in a row, I knew this was serious, so I slipped out of the office to listen. My heart sank as I thought about the last few weeks—she was living with my 92-year-old grandma, who had been falling frequently. But then I heard it: “A guy from Match.com messaged me!” she exclaimed. “I’m freaking out! What do I say back?”

I had some experience with online dating, having worked freelance writing profiles for a dating service. I figured if my clients, many of whom were Baby Boomers, could navigate the dating scene online, so could she. However, I didn’t anticipate the flood of emergency calls. “He said I’m beautiful and charming!” she gushed when I called her back. “And he sent me a picture of a rose! How cute is that? It looks like a cartoon! Can you believe he called me beautiful?”

I was thrilled she was stepping outside her comfort zone, but I also wanted to gently remind her that messages like that are often sent to several women at once. I mean, the rose was sweet and all, but still. My mom, who had little experience with technology, was struggling to get the hang of things—like picking a username (she chose “delusins,” which led one guy to ask if she was delusional!) and almost wiring $1,000 to a guy who clearly had bad intentions. Then there was the suggestion from her grandma’s nurse to post swimsuit photos. Talk about a no-go!

I had to step in and coach her on the basics of online dating: how to spot generic messages from guys just copy-pasting the same lines, avoid getting sucked into endless texting without meeting, and post a few modest pictures (a nice headshot, a medium shot, and a full-body shot—definitely no bathing suit photos!).

One day, a 65-year-old client of mine remarked, “If dating is tough for you, imagine what it’s like for your mom!” That hit home. Ever since her second divorce when I was 9, she had mostly lived with my grandma, occasionally dating men she met through work or mutual friends. But now that she was retired and most of her friends were happily coupled, she was facing some solitude. With my grandma’s health declining and moving to assisted living on the horizon, I thought a little dating could provide my mom with some joy and distraction.

“Jamie, what should I say back?” she asked during one of our many phone calls.

“He mentioned he plays golf,” I replied. “Why not ask him about his handicap?”

She responded with, “My daughter said to ask you about your handicap.” Oh, Mom! I reminded her to rephrase it in her own way, so he wouldn’t think I was the one interested. I chuckled at the memory of her double-checking my English homework, always saying, “Every word counts.” Now, I was echoing those same sentiments as we crafted a thoughtful response to the mystery man.

Then one evening, she squealed with excitement, “Jamie, he wants to meet in person!” I felt a rush of elation, as if I were the one going on a date. But I also played the role of the protective parent, advising her on what to wear (something cute but not too revealing) and stressing the importance of meeting in a public place, informing a friend about her whereabouts, and having a plan if things went south—just like she advised me back in high school.

After each date, she’d call to fill me in, often saying, “It was terrible!”—though sometimes I’d hear, “I think I’m in love!” I didn’t pry for every detail, but it was fascinating to hear about her experiences, like whether he treated her like a lady, if he was a gentleman, and how they connected. It amazed me that men in their 60s could be just as romantic as those in their 30s and 40s—showing up with actual roses instead of cartoon ones or standing when she excused herself. On the flip side, some were as sleazy as they come. I found myself giving her advice like “Don’t feel pressured to kiss him,” and “He’s not the one for you,” realizing I could use some of that wisdom in my own life!

Months into her online dating adventures, my grandma moved into an assisted living facility. Now, my mom brings her boyfriend along for visits. It’s been a wild ride, and I’m glad I got to be her coach through it all.

Conclusion

In summary, my experience coaching my mom through the ups and downs of online dating has been both challenging and rewarding. It was a journey of rediscovery for her, and a reminder for me that love and connection can come at any age. If you’re curious about home insemination or related topics, check out more at this link, or explore this authority resource for more information. For a comprehensive look at fertility and health, consider visiting this excellent resource.