What Online Dating In My 50s Taught Me About Myself
“Motherly wisdom guided me to discontinue online dating.”
My mother was lying half asleep with her eyes closed in a hospital room after heart surgery and suffering from a stroke. She periodically spoke, mostly random thoughts, and I was cherishing all of them. “I long for my husband,” she said through tears, and I tried to console her by saying that Dad’s spirit was with us in the room. “You are lucky you had such a good husband for 36 years, I still haven’t found one,” I reminded her. She suddenly opened her eyes, turned her head, and pointed at me. “Stop looking!” she said. And then she closed her eyes and fell asleep.
I am a 52-year-old woman. I’ve never been married, and I have no children. I’ve never actually been engaged. (Supposedly some rings were purchased, but I never saw them.) I think there were about three men that I seriously considered marrying or becoming their lifelong partner. I’ve lived an unconventional life, both personally and professionally. I enjoy a freedom that allows me to explore and develop my interests—ocean swimming, painting, mosaics, writing, traveling, hiking, psychology, meditating, and cooking—and I’ve grown very accustomed to living alone. I cherish my independence. I am happily single but sometimes yearn for a partner that will enhance my life. I don’t want drama and constant complications. I won’t tolerate bread crumbs from a man because I know I deserve the full loaf.
“I won’t tolerate bread crumbs from a man because I know I deserve the full loaf.”
I have dabbled in online dating over the past few years, dating men between the ages of 45 to 65. Those dates have given me enough material for a stand-up comedy routine. There was the math professor who revealed he had a foot fetish and a small “member” on our first date; the newly separated guy who agreed to a monogamous relationship and then after a few weeks, asked if we could make out with other people; the seemingly nerdy guy who told me that he and his ex-wife regularly participated in threesomes; the engineer, who hoarded electronic equipment and slept with a large synthesizer; and the techie dude whose house was ruled by his operating system and was offended when I jokingly made rude comments to “Siri.”
I’ve used about four different online dating platforms throughout the years. They are all pretty similar, although the newer sites seem more impersonal with the swiping left and right features. I typically look at all the pictures and read the content unless the main photo is a turn-off—such as bathroom selfies, a picture of a couple, anyone wearing MAGA gear, or a guy who looks like he just rolled out of a cardboard box on the street. Other red flags include using a moniker rather than a real name; no occupation listed; a list of all the things they don’t want in a partner; sexual comments; men in “open” relationships; or couples looking for a threesome.
When I do match with someone, and we seem to have a good connection, I will share my number after a message exchange—sometimes the same day, sometimes after a few weeks. I would rather speak to the person and get a feeling for them sooner rather than later. I tend to like men who are decisive and want to actually talk and meet within a week or two. I don’t have the bandwidth to message over a long period of time with several men.
First dates are usually meeting for coffee or over a meal. I rarely get nervous anymore, and I dress appropriately for the location, which I often pick—quiet locations where you can actually hear each other well. I also let a friend know about the date, and I text them after to let them know I’m safe.
“My mother died three weeks after she told me to ‘Stop looking!’ The phrase lingers in my mind and heart.”
My mother died three weeks after she told me to “Stop looking!” The phrase lingers in my mind and heart. The message seemed divine because she rarely spoke the last few months of her life and often wasn’t very alert. When she said that phrase, she came to life in that brief instance, imparting her wisdom. But when December approached last year—the first holiday season without my mother—I felt lonely and vulnerable, so I hopped back online. I met a man who was hilarious, creative, and empathetic regarding the loss of my mother. He was also recently separated, between jobs, and admitted to addiction issues, so I knew it was not going to last. After a month, we decided to part as friends.
My mother’s words “Stop looking!” streamed back into my consciousness as I felt like I failed her and myself with that final online dating experience. I had already vowed to “stop looking,” but I dated him anyway, even though I knew it wasn’t going to last. Then I realized I didn’t fail—I was simply human and wanted some comfort and distraction during the first holiday season without my mother. That last brief online dating experience served as a good reminder that online dating wasn’t the healthiest option for me.
My mom’s simple phrase, “Stop looking!” grows deeper in meaning as time passes. I realize now she wasn’t just talking about dating men. Everything I seek or need is within me. My life purpose is about pursuing my passions: writing, art projects, travel, open water swimming, advocating for marginalized people, and spending time with loved ones. I have “stopped looking,” and I am content with moving through life with an open heart and mind. I focus on connecting and maintaining close relationships with friends and members of my family and staying open to new experiences and people.
“My mom’s simple phrase, ‘Stop looking!’ grows deeper in meaning as time passes. I realize now she wasn’t just talking about dating men.”
The following Warsan Shire quote sums up my attitude about entering into a relationship, “My alone feels so good, I’ll only have you if you’re sweeter than my solitude.”
Stefanie Vallejo Monahan is a special education teacher in San Luis Obispo County, CA. She has a BA in Journalism and a MA in Special Education. She enjoys spending time in nature, travel, organic foods and creative endeavors. She is the proud aunt of 6 nieces and 3 nephews.