Stepping into the Twilight Zone of Online Dating

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Sometimes you know that a thing isn’t a good idea, but you get swept up in it anyway, sort of like Dorothy and Toto whirling away to Oz. There’s always a beginning, a point when you have a choice. Choose one direction and life goes on as before; choose another and you end up being chased by a wicked witch. Never let someone else choose the direction for you, especially your two best friends.

“Online dating, you should try online dating. You’re a smart, interesting woman and your problem is that you don’t meet any decent men.”

Best friend number one and best friend number two basked in the glow of their mutual satisfaction as they offered the obvious solution to my lack of a love life.

Me: “Smart and interesting are code for unattractive.”

“Don’t be so negative. You’re an attractive woman; you just have to sell yourself more.”

I should have pointed out that women who sell themselves often end up developing unwanted relationships with local law enforcement, but like Dorothy, I got swept away and the next thing I knew, I was composing my first personal ad.

I selected a site called because it was inexpensive (cheap). After answering a few questions about myself, I was given the opportunity to select the characteristics that I wanted in a man. They didn’t have breathing on the list, so I picked a few other things—mature, tall, employed, etc. Then I composed a couple of paragraphs about me and waited. 

My first hit was from a twenty-three-year-old who was neither mature nor employed, but he was tall. I also assumed that he had difficulties reading. I sent him a polite note explaining that I thought that the difference in our ages was too great. He sent me a note back with a detailed description of a certain part of his anatomy and a caution that I didn’t know what I was missing.

The next contact was from a gentleman seeking a Proverbs 31 woman. I checked my bible and realized that there could be a problem with a difference of opinion with this match. Proverbs Chapter 31 describes the ideal wife as a woman who “rises while it is still night and distributes food to her household” and “at night her lamp is undimmed.” When does she sleep? Realizing that I would only disappoint him, I decided to not respond at all.

By this point, I was whining to my best friends that this was not going well.

 ”You need to sign up with a better dating site, something more upscale.”

I dutifully registered my profile at My first email from included twenty possible matches with a percentage ranking indicating how closely each matched my criteria. I was pretty excited and began checking out each potential match by reading his complete profile. Mike, Joe, and Rufus all wanted children. I’m fifty-one years old, so figuring that this could be a deal breaker, I moved on. Hubert, Sam, and Charles were undecided as to whether or not they wanted children and indicated that it was a maybe. Then there was Mr. Big, who was unhappily married and was looking for a discreet woman. (All names have been changed to protect somebody!) I entered into email communication with one gentleman who seemed quite nice, but he lived in Oregon and didn’t like to travel. He suggested that I come visit him, but I’ve seen Psycho more than once and couldn’t get that shower scene out of my head.

So far, I had spent about $80 and I hadn’t had a single date. I was ready to give up and accept my single, never married status as permanent. But my best friends were full of encouragement.

“You give up too easily! You’ve got to give the process some time.”

By now, my sister was a member of the cheerleading squad, telling me of women that she knew who had met their future husbands online. Pumped up, I decided to register with the big kahuna of matchmaking sites, It took over an hour just to answer the questionnaire that would be used to match the twenty-nine points of compatibility that would guarantee that I would connect with my selected matches.

To my delight, the next day I had email from announcing that I had several matches. Unlike the other sites, eharmony guides you through the first levels of communication with an exchange of questions/answers, must haves/can’t stand, and finally, open communication.

Perhaps it was the more involved registration process, but there was definitely a more serious tone at eharmony—no unhappily married guys seeking discreet women! I made it to open communication with a few and went on some decent dates, but there were no bells and banjos with any of them. 

Then I met J. We hit it off in our guided question exchange. When we began open communication, our first conversation lasted four hours. (It was by telephone; he lives out of state.) Over the next few weeks, we talked often and for extended periods of time. I was in heaven. He was witty, intelligent, had a great sense of humor, and was kind, compassionate,  and tall!

Unfortunately, this does not have a happy ending. The girl doesn’t get the boy; the boy doesn’t want the girl. The good thing is that no one dies. 

Like all of the online dating sites, encourages you to post a recent picture of yourself, which I dutifully did. However, when I set up my account, I selected the option that in order to see my photo, the other person’s photo would have to be available as well. I then promptly forgot that I had selected this option. J had no photo posted and as a result was unable to view my photo.

Blissfully unaware that J had no idea what I looked like, I assumed that he liked short, fat ladies, until he asked me to read him some of my poetry over the phone. Call it fate or bad luck; the poem that I selected to read is called For Women Who Wait. The best summary of the poem is that the speaker bemoans her lack of attractiveness and her loneliness.

When I finished the poem, there was a moment of silence, followed by a question, “You don’t consider yourself attractive?”

The honest answer to that question is maybe. It depends on my mood. I write poems about moods, impressions, and feelings that I may have experienced directly or merely observed. 

I did the only thing that I could; I immediately sent J a photo of me and waited. He called the following weekend and I was grinning from ear to ear. I assumed that while I’m no Halle Berry, that he at least found my visage passable. We talked as usual for a couple of hours, but I needed to know.

“I assume you received my picture.”

“Yes, I did, thank you,” a polite response but it told me nothing. I breathed deeply and took the plunge.

“No pressure or anything but I need to know where you see us going with this relationship. Do you see romance in our future?” There’s nothing like being direct.

“I really like you, I love talking to you, but … (you can hear a but coming from a mile off) … I tend to be attracted to women who are rather svelte.”

He actually said svelte. He has a good vocabulary; not very many people use the word svelte in everyday conversation.

J and I are still friends and we speak often; we’ve even visited in person once. We have a lot of common interests and we continue to have marathon conversations. I keep asking myself what I learned from this experience. So far, I’ve come up with three things:

1. Even if he asks you to read your poetry to him, don’t.

2. You can spend a lot of money and still not get what you want.

3. Following the yellow brick road isn’t always a good idea.


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