The Time I Became an Online Dating Coach for My Mom

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“Laura, I need your help!” My mom’s voice echoed in my head as I listened to her frantic voicemail outside my home office. After a string of five missed calls, I knew it had to be serious. As her 68-year-old voice crackled through the speaker, I braced myself for the news. She had been living with my grandmother, who at 93, had been facing some health challenges, including frequent falls.

“A guy from Match.com messaged me!” my mom exclaimed. “I’m not sure how to respond!”

With my experience crafting online dating profiles for e-Cyrano.com, I felt a spark of hope. If my mom’s peers could navigate the world of online dating, surely she could too. However, I quickly realized that my evenings were about to be filled with her urgent calls. “He said I’m beautiful and charming!” she gushed during our first call. “And he sent a picture of a rose! It’s adorable!” My heart warmed, but I couldn’t help but think that his message was likely a generic compliment sent to many others. Still, it was a step forward for my mom, who was not exactly a tech whiz.

The truth is, she had no clue what she was doing. From her awkward username “delusins,” which prompted one guy to jokingly ask if she was delusional, to almost sending money to a clear scammer, she was struggling. A particularly bizarre suggestion from my grandmother’s nurse to post swimsuit photos left me shaking my head. I had to step in and provide some coaching—teaching her to spot copy-and-paste messages, avoid the pen pal trap, and select a few modest, flattering pictures.

One day, a client of mine, who was 65, remarked, “If dating is tough for you, just imagine how it is for your mom.” I thought about how my mother had lived with her own mother since my parents’ divorce when I was nine. While there had been boyfriends along the way, many of her friends were in committed relationships now that she was retired. With my grandmother being her one constant companion, I could see the need for my mom to seek companionship outside their shared home.

Encouraged by the notion that dating could offer her a distraction from the weight of health concerns, I supported her venture into online dating. It could be a source of joy—someone to go to movies with, share dinners, or simply chat about life outside of doctors and Medicare representatives.

“Laura, how do I respond?” she’d ask during another call. “He mentioned he plays golf.”

“Ask him about his handicap,” I suggested.

In typical mom fashion, she wrote back, “My daughter said to ask you about your handicap!” I quickly reminded her to rephrase it in her own style to avoid giving the impression that I was the one interested. It was like a role reversal of when she would review my homework, emphasizing how “every word counts.” As we crafted a thoughtful reply together, I made sure to encourage her to personalize her responses to reflect genuine interest.

Then came the day when she squealed with excitement, “Laura, he wants to meet in person!” I felt a rush of pride and nervousness, almost like I was the one going on a date. I offered her advice on attire (something feminine yet tasteful) and reminded her to meet in a public space, inform a friend of her whereabouts, and have an exit plan if things went south. After each date, she would call to share her experiences, alternating between “It was dreadful!” and “I think I’m falling in love!”

While I didn’t pry for every detail, it was fascinating to hear about her experiences—how some men were charming and romantic, while others left much to be desired. I often found myself giving her the same advice I needed to hear: “Don’t feel pressured to kiss him,” “He’s not the one,” and “Never settle.”

After a few months, my grandmother transitioned to assisted living, and my mom began bringing her new boyfriend along for visits. This journey of online dating not only brought excitement into her life but also forged a new chapter in her personal story.

If you’re interested in exploring more about fertility and home insemination, you should check out this resource on treating infertility by ACOG. For those considering at-home insemination, consider visiting CryoBaby for their reliable kits. And for more insights into navigating relationships and parenting, don’t miss our other blogs.

In summary, my unexpected role as an online dating coach for my mom has not only opened her world but also reminded me of the importance of love and companionship at any age.


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