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Monday, May 11, 2026 at 8:04 AM
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Dating in the digital age

By Moses Leos III.


Let’s face it – it’s tough being single in this hustle and bustle world. It’s worse for introverts like me who don’t interact with others much. 


For the record, I have my reasons for being an introvert. No, I will not disclose them. 


But for so many, normal dating constructs have always been troublesome. It’s hard for the meek to make a pass at someone. 



Thankfully, a wise person combined the practicality of the internet with the difficulty of dating.  





Christine Thorpe and Thomas Saunders enjoy an afternoon together, while Moses Leos III searches for love online. (Photo by David White)


From eHarmony to farmersonly.com and everything else in between, online dating has taken over the American consciousness. 


Statistics speak for themselves. According to an Oct. 2013 study by the Pew Internet Research Center, one in ten adults have used dating websites or dating apps. Nearly 40 percent of those who are “single and looking” use such websites. 


Some dating sites claim they can help find lasting relationships. 


Of course, the biggest draw is accessibility. With many sites having iOS and Android apps, it’s easy for potential daters to keep track of their, well, dates.   


With all of that in mind – the statistics and the seemingly high success rate – I’d figure I give this whole phenomenon a try.  After all, I’ve been single since my college days. It’s bound to work, right? 


I chose OkCupid and Plenty of Fish.com (POF). Both are “free,” meaning you can message a prospective date without cost. Both sites offer extras, but I opted for the no cost version. 


I started the process like everyone else – filling out who I am and what I’m about. I ran into some trouble completing this task, struggling with finding what makes me unique. 


According to the Pew study, 54 percent of Americans said their online dates “seriously misrepresented” themselves. 


Hoping to avoid that trap, I went with the honest approach, telling everyone I’m a quiet introvert who’s also an intrepid sportswriter (okay, maybe not the intrepid part).    


And then there were the personality questions. They ranged from assessing social issues, interaction, previous relationships, pet preference and even sex. 


The way both sites approached their questionnaires was vastly different, but the end result was the same: to find people similar to you. 


It was nice to browse through the different profiles. At the same time, that misrepresentation issue lingered in the back of my mind. 


Finding a few woman whose profiles I liked, I finally mustered up the courage to message them. 


“What’s the right thing to say?” I wondered.


That’s when Google became my best friend. I consulted about 10 different websites, each spelling out the best way to start an online dating message. 


The consensus was clear: Short, sweet, to the point. Maybe a little humor, and for God’s sake, be a little inquisitive. 


I spent roughly an hour on each message, trying to find the best thing to say. But I ran into online dating’s dirty little secret: Not everyone responds back. 


Sure enough, the first three messages I sent were lost in cyberspace. Quoth Kurt Vonnegut – “So it goes.”


It took a week before I finally got a response. The good news? We had a lot in common. 


We chatted online, sharing our likes and interests. I was impressed with what she had to say. The time came to make or break it. I had to ask her out.


Turning back to Google, I found some ideas. She eventually agreed to meet. 


On the “big day” I was a bundle of nerves.  My mind was racing; I was not 100 percent sure she was who she said she was. 


Fortunately, the experience went well. We talked for at least two hours, sharing more tidbits of our lives. It was an enjoyable experience. She even agreed to see me again. (Yes!) 


Since this online dating experience went well, I decided to write about it. But I can see how something like this could be negative. It’s way too easy to mislead others, both in who you are and what you look like. 


I always think honesty is best – be true to yourself and be willing to take a chance. Things may just work out. 


So goes dating in the digital age. 


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