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I Had 75 First Dates Before Finding Love in My Late 60s
After decades in a relationship, I reentered the world of dating. Here’s what I learned about navigating dating apps and spotting red flags — before finally discovering a true connection offline
Newly single at 66, the author turned to dating apps, with mixed success.
Margaret Flatley
When I was middle-aged, I was in a relationship that I thought would be the love of my life. My partner and I made long-term plans, and we even imagined our graves would be as close as a couple in bed. We blended our families and had a son together. But our relationship ended, despite years of counseling.
I had to make a new beginning as a single person at age 66. I tried to keep in mind the life lessons I’d learned the tough way. I knew that a steamy romance didn’t necessarily lead to a harmonious and lively home. I deeply believe that passion is still important for older adults, but it’s not like when we were young, when the whole Kama Sutra of positions was possible for us. I was seeking a woman I found attractive, but mainly I was looking for someone with overlapping interests and who made me feel emotionally safe.
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It had been three and a half decades since I’d dated. I signed up for the apps for singles and didn’t have a clue how to present myself to attract the kind of woman I was looking for. I was fortunate that my cousin Pamela, who’d also recently been single as a senior, brainstormed with me to craft a profile. She gave me ideas for describing myself in a way that showed my sense of humor and the type of person I hoped to date. One phrase we came up with was, “We all have baggage — I hope yours has wheels.”
I deliberately didn’t pick profile photos that hid my baldness, or snapshots from previous decades. The last thing I wanted was for someone to meet me for the first time and think, “This guy doesn’t look a bit like his photo.”
I posted my profile but wasn’t flooded with matches right away. I wonder if many retirees on the apps secretly nurse a hope that someone much younger will seek them out. That wasn’t me. I wanted a partner who remembered that Woodstock wasn’t just the little yellow bird in the Peanuts cartoons.
Author Zack Rogow and his later-in-life love traveled to Japan together.
Courtesy Zack Rogow
But I did begin dating. In fact, I had 75 dates. In some cases, it was the woman who didn’t want Date #2, and sometimes I chose not to continue.
One date was memorably awful.
I met a woman online who lived a good 60-minute drive from my home. I drove to her town to meet her at a café. When she didn’t show up after 45 minutes, I called her. She said, “Oh, are we still meeting? OK, I’ll be there soon.” When she finally showed up, she didn’t stop talking for two hours, and I couldn’t get a word in edgewise. When at last I was able to make an exit, she said, “Let’s do this again. You’re such a great conversationalist!”
Most of the women I met were remarkable people, highly accomplished and very pleasant to interact with. But those dates didn’t result in a lasting relationship. One woman I had a brief affair with was incredibly smart, funny and accomplished. I also found her attractive. But she insulted the waiters when we went out to dinner. Little things like that can be tip-offs about a person’s true nature.
Another woman I had a short romance with asked me right before she broke up with me, “Do you ever wear jeans?” Ouch. But she was right about my geezer khakis. Am I still relationship material? I wondered.
Travel is one of the interests Rogow shares with his partner.
Courtesy Zack Rogow
I finally met my current partner through mutual interests, not online. I translate French literature, and I launched a new book at a private event at a friend’s house. A woman who wasn’t on the invitation list appeared; it turned out she had a mutual friend with the host. She asked a really good question and came up to me afterward to suggest a similar book I might want to translate. That woman had a head of blond wavelets and eyes the color of the sky in southern France. I asked her if we could meet to talk about the book she recommended, and the rest is history. We’ve been living happily together for six years.
During that new and unexpected chapter in my life as a single man in my late 60s, I wrote poems to process the experience. Many love poems are about the heated passion of youth, and that’s great. But I wanted to write about how rare it is to find someone to love as an older person, someone who becomes your sweetheart after a lifetime of seeking.
AARP essays share a point of view in the author’s voice, drawn from expertise or experience, and do not necessarily reflect the views of AARP.
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