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After 34 Online Dates, I May Have Finally Found the One

But this divorced woman had to kiss a lot of frogs first.

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illustration of woman finding a perfect date among many different men
Justin Tran
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I’m 56 years old, divorced for three years and have been on first dates with 34 different men. These meetings came primarily from online sites including Bumble, Hinge and Match.

If you had asked me a decade ago if I’d ever be divorced, I would have smirked and thought: “I’ll never be part of that club!” Well, fast forward to August 2020, and there I was, plunk, a new member of a club I never believed I’d join.

For quite some time, I clung to the hope of salvaging my 26-year marriage and sustaining a lifelong partnership. With two young adult sons setting out on their own journeys, the idea of our family breaking apart was heart-wrenching. Divorce felt like stepping into a storm that engulfed me, leaving me battered and bruised.

Fortunately, storms do eventually pass and, as the downpours stopped and the winds calmed, standing on my own presented me with an opportunity for healing and self-discovery (thanks to the help of a great therapist). Eventually, I regained my desire to go on a quest for love — albeit with some trepidations.

Ugh! Did that mean I needed to start regularly shaving my legs? And was I going to eventually have to get naked in front of someone new? Yikes! My body looked completely different now than when I met my husband at 24.

And so with newfound strength and cautious optimism, I ventured into the world of dating apps — always sharing my location with my sister, just in case I needed a swift exit.

Swiping through profiles became a daily ritual along with my morning coffee. The process was both enlightening and exasperating. Conversations would spark and fizzle out, and sometimes those I thought could be prospects would vanish into the digital abyss.

This vanishing act happened with one man who seemed promising after two dates. The second date included a hike and a sweet picnic lunch (that he had packed!). I texted him to thank him for the delightful afternoon. I didn’t get a response, so a day or two later I texted again — still no response.

As the kids would say, I was “ghosted.” Was it something I said? Was it my frizzy, wild hair on that humid August day? I’ll never know, but it did leave my ego a bit bruised.

I did find there were many great, honest men out there, but certainly a few who took creative license in their profiles. Pro tip: If a guy says he's 5'11", chances are he's closer to 5'8".

In my profile, I indicated I was only interested in non-smokers. Then came my date with one man I met for dinner, who reeked of cigarette smoke when he hugged me hello. To top it off, as soon as we sat down at the table, he casually took a breath mint out of his mouth and plopped it next to his water glass. Was he planning to put it back in his mouth after dinner?

Other dates felt like a chore, like the guy who spent two hours talking about his ugly divorce, his challenging relationships with his kids and how much he disliked his job. He actually broke down in tears during his monologue. I ended up feeling more like a therapist than a date. This was one of those nights when I would have much preferred to be curled up at home in my pajamas with a tub of mint chocolate chip ice cream, watching Netflix.

Then there was the time during a steamy good night kiss, my date decided to pause and reveal his STD history. I genuinely appreciated his honesty but talk about a mood killer!

Despite telling my mom I’d let her know when there was someone interesting in the picture, she predictably asked me during each phone conversation if I had met anyone worthwhile. As moms do, she talked about her friend’s daughter who embarked on a similar online journey, and finally found love on her 34th date. I decided to keep my own tally, predicting it would take around 100 first dates before I found my one.

Turns out, I was wrong.

I spoke to my 32nd date on the phone a number of times — some conversations lasting for over an hour. He was funny, self-deprecating, very smart and, like me, he loved to cook. Also, we were close in age which checked one of my boxes.

Despite the online dating fatigue that had started to set in, I agreed to meet him for a Sunday brunch. I knew when he brought me flowers and a loaf of bread he had just baked that he was, if nothing else, a truly nice guy. I learned that he was widowed after a happy 32-year marriage and, like me, had never expected to be back in the dating game. After meeting him, I did go on two more first dates with others, bringing my tally to 34. Though I had a really good feeling about number 32.

Well, number 32 and I have been together for more than a year. Our time together has all the excitement you’d associate with a new relationship and a level of maturity and communication that just wouldn’t have been possible in our 20s. We’ve spent many of our dates cooking together, playing pickleball and traveling.

The biggest trip was to Portugal and we found that we are very compatible travel partners. He tells me I snore, but that it’s “cute." So, after dozens of misfires, things right now are really good. I am emerging from a challenging time where I felt like damaged goods from a failed marriage. Both therapy and compassion from number 32 have helped greatly. So after all those dates, I’ve found someone who deserves a whole LOT more dates — a Mr. Right? Not sure yet … but a strong maybe.

For those who, like me, find themselves single after 50 and yearning for companionship, my advice is simple: get out there. It’s worth the effort. Keep in mind, though, that you may need to kiss a lot of frogs to find your prince (and some may not be the best kissers).

Have any of you tried online dating? Let us know in the comments below.

Follow Article Topics: Relationships
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