“Carmen, it’s urgent,” my 66-year-old mother’s voice echoed in my mind as I listened to her voicemail outside my office. After she called me multiple times in quick succession, I knew I had to take a break from work to hear her out. My heart raced as I anticipated her next words. She lived with my 92-year-old grandmother, who often resembled a second mother to me, and had been experiencing frequent falls lately.
“A guy from a dating site messaged me!” my mom’s voicemail continued, her excitement palpable. “Call me back! I don’t know how to respond!”
As a freelance writer for an online dating profile service, I had helped many clients in her age group, the Baby Boomers. If they could venture into online dating, I figured she could too. What I didn’t foresee were the emergency calls at all hours. “He said I’m beautiful and charming,” she exclaimed when I returned her call. “Then he sent a picture of a rose! It’s adorable—like a cartoon. He called me ‘beautiful!’ Do you know how long it’s been since someone said that to me?”
While I wanted to remind her that he might be sending that same line to multiple women, I was genuinely thrilled that she was stepping out of her comfort zone. My mom was not very tech-savvy, let alone experienced in the world of online dating. From struggling to choose a username (her attempt, “carlovmama,” led to one man asking if she was crazy!) to nearly sending $1,000 to a clear scammer, her journey was filled with missteps. Then there was that awkward suggestion from a nurse to post swimsuit photos—definitely not her style! I had to step in and began to coach her on the ins and outs of online dating: recognizing copy-paste messages, steering clear of the online pen pal trap, and selecting tasteful photos (a close-up, a medium shot, and a full-body shot—no swimwear!).
One day, a 65-year-old client of mine remarked, “If dating is tough at your age, just imagine how it is for your mom.” It made me reflect on her life post-divorce when I was just nine. She had lived with my grandmother ever since, occasionally meeting men through work or friends, but now that she had retired and her friends were happily partnered, she was largely alone. Most of her phone calls were from Medicare representatives or doctors, not potential romantic interests.
While my mom didn’t necessarily need to date, I was pleased she was trying. We both understood that her constant companion of the last three decades, my grandma, would soon need to transition to an assisted living facility. My mom would be left to navigate life alone. Though she was accustomed to being single, I thought dating could provide a welcome distraction from the burden of her current reality—grandma’s falls, frequent emergency visits, and discussions about her care options. It would be nice for my mom to have someone to enjoy outings with—movies, dinners, concerts—and to receive phone calls from people who weren’t discussing healthcare.
“Carmen, what should I say back to him?” my mom asked on another call. “He mentioned he plays golf.”
“Ask him about his handicap,” I suggested.
She promptly typed, “My daughter said to ask about your handicap.” Oh no, I thought! I reminded her to rephrase it in her own words so he wouldn’t think it was me interested in him. I recalled how she would meticulously review my schoolwork, emphasizing, “Every word counts.” Now, I was echoing that advice as we crafted a thoughtful message that demonstrated she had read his email and profile.
One evening, she squealed with excitement, “Mia, he wants to meet up in person!” I felt a rush of joy, as if I were the one going on a date. Yet, I also felt like an overprotective parent sending her off into the unpredictable waters of dating. I advised her on what to wear (something feminine yet modest), reminded her to meet in a public place, inform a friend of her whereabouts, set a time limit, and ensure she had an exit strategy if things didn’t go well—similar to the advice she had given me two decades earlier.
Afterward, she would call to share her experiences, often saying, “Mia, it was terrible!” but occasionally, “Mia, I’m in love!” While I didn’t pry for every detail about her dates, I found it fascinating to hear about their outings—where they went, if he was courteous, whether he paid or suggested splitting the bill, and what they had in common. I realized that some men in their 60s could be just as romantic as those in my 30s and 40s (showing up with real roses, not just cartoon ones, or standing when she left the table). Conversely, some were equally inappropriate—overly familiar and disrespectful. I often found myself advising her, “Don’t feel obligated to kiss him,” “Nope, he’s not the one for you,” and “Don’t settle.” Ironically, I found I needed to heed that same advice for myself.
Several months into her online dating escapades, my grandmother did move into an assisted living facility. Now, my mom brings her new boyfriend along for visits.
In summary, unexpectedly stepping into the role of online dating coach for my mother opened a new chapter in our relationship. While navigating the complexities of digital romance, we both learned valuable lessons about love, connection, and the importance of stepping outside our comfort zones.