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My Funniest Online Dating Horror Stories

Yes Yes. It is absolutely true that ultimately online dating worked quite well for me. But having given it some thought, I wanted to be honest with you about something. It’s not like every dating is a wonderful stream of perfection.

Sure, I met a lot of great women and had a great time over the years … culminating in meeting Emily on But along the way, especially in the beginning, I certainly found my share of sometimes funny and sometimes downright nightmare situations.

Here are the four most memorable:

1) It is not what the doctor prescribed

Very shortly after my divorce in 1992, I received a “spam” message in my inbox to which I responded. Believe it or not, you hadn’t even heard of online dating before. This ad said that I could meet the woman of my dreams on your site, so I was intrigued.

The next thing you knew, I had put up with everything they charged and I started looking at the photos of the women they had listed.

To be honest, this was not exactly the most visited site on the net. Who knew there was a out there? Then inevitably I found exactly one A woman I found interesting, a brown-eyed blonde with a friendly smile.

I emailed him, probably with something unconvincing like “You seem nice. Maybe we can get along. Would you like to talk?” Remember, this was the first day for me in the world of online dating.

Call it “beginner luck, but she replied. It’s crazy, huh?”

Well, one thing led to another, and there we were sitting across from each other at the table during dinner. The fact that you shouldn’t have been paying for dinners here a long time has been duly noted and is beside the point, so please skip that for now and read on.

In the middle of dinner, he begins to talk about his medical problems.

Never talk about your medical problems on the first appointment. I don’t care if you’ve known the person for ten years, let alone ten minutes.

Between bites of whatever he was eating, he bragged about how he had chronic kidney stone problems and how hard it was to be able to pass them without even flinching today.

Unfortunately, she took my casual attempt to deflect the discussion as disbelief.

“You don’t think I have kidney stones? Here … look …”

Having started looking in her purse, she soon produced a small vial of medicine.

I thought to myself, “This girl has to be kidding me. I believe her. She doesn’t have to prove her case by showing me her recipe.”

I should have been so lucky.

By pressing and twisting the childproof cap, the bottle was opened and the contents were soon poured into his hand.

“Look, look at this … it has to be at least the size of a pea, right?”

With a freshly manicured thumb and index finger, he pulled out the largest unit in an impressive collection of similar objects he held.

Yes. It was the largest kidney stone I’d ever had.

This woman collected her kidney stones. And he took them with him everywhere, apparently.

I don’t really remember what I said or did. But I do remember there was a second date, believe it or not.

2) It is not a strip Mall, Sweetie

Not long after the “kidney stone chick,” I met another woman from the same site. She was a Hispanic girl with flawless skin and booty that would have made Sir Mix-A-Lot slam on the brakes. He said a lot “honey”.

He still hadn’t learned the part about not taking women to expensive dinners on first dates, so they were at one of the best sushi establishments in San Antonio.

She was great. She was smart and loved to laugh. Beyond that, she was a great flirt. Clearly she was digging me.

We had ordered two glasses of red wine and the conversation turned to what he did for a living.

“So you said you were ‘self employed’. What exactly do you do?” I asked.

As she replied, I took a sip of Merlot. And it was at that point that I discovered that all those “spit” antics you see in old school comedy sketches are rooted in factual reality.

It took me everything I had in reserve so as not to spill grape juice everywhere.

“I run a chain of strip clubs, honey,” he had announced quite naturally.

Sitting across from me was a decidedly elegant woman, whom I had picked up from a decent house in a nice neighborhood.

“You mean, like a strip Mall… right … with the nail salons, a tanning place and a Chinese restaurant. “

“No silly! LOL! I mean like … you know … clubs. The guy with Girls. “

Now, if you know my style by now, you already realize that the date was about to end.

However, it was like a train wreck. He couldn’t look away.

And I asked him the inevitable question.

“Yeah, well … my ex ran the day-to-day operations and I pretty much handled the books. But he let the ‘interview process’ go too far too often, and I couldn’t trust him anymore. business in divorce settlement. “

It was then that I told him the truth.

“I’ve never been to one of those places in my life and I don’t see any reason to start now.”

Uh oh.

You may have lit a Roman candle. That girl practically attacked me as soon as we left the restaurant. I tried to handle things to the best of my ability at the time, but let’s just say she wasn’t a happy camper.

When I got home, she had already emailed me the nude photos from her “Adult Friend Finder” profile (which was my first introduction to that particular reality). “This is what you missed. GOOD LUCK !!!” it was the only line that accompanied the photographs.

3) June Carter charge or cash

He should have known better, considering the only photo he had attached to his profile was blurry.

And in the bottom of my heart, I really knew better. Suspecting that this particular date might not go so well, I invited her to dinner (yeah yeah … wasn’t he stubborn?) At 5.30p.

I walked into Chili’s or TGIFridays or whatever, and immediately had that nauseating feeling that everyone online daters experiences at one point or another. Specifically, the one where you see someone waiting alone at a table that vaguely resembles the person you were hoping to meet as much as burnt toast looks like the perfectly good slice of bread you tossed in the toaster and forgot.

My first honest thought was: “OMG … who replaced the woman with the cute smile in the profile with June Carter Cash!”

I was too “Mr. Nice Guy” to turn around and run out of town right away, so I mustered my gut strength and walked over to the table.

The conversation was forced from the beginning. He began to make a weak attempt at flirting.

The woman was at least 55 years old. And he’s not a very attractive 55-year-old man.

She was dressed in solid black with a bunch of stainless steel junk and fringe, like she was a legend from “The Grand Ole ‘Opry” or something.

The thickness of her Texan accent was dwarfed only by the thickness of her black eyeliner.

Finally, she excused herself and went to the ladies’ room, offering me blessed relief from the impending regurgitation.

It was then that the waiter came to the table and asked if I wanted another beer. “DO NOT!” I proclaimed, soon apologizing for the brusque tone that neither he nor I had anticipated.

“Okay, um … what about your mom?


“Would your mom like another beer?”

Suddenly reminded that one must take oneself a lot less seriously to get the most enjoyment out of life, I laughed.

I was still recovering when Mrs. Cash came back to the table.

Having ordered a small garden salad (who could eat after all?), My focus was on saying as little as possible in hopes that she would finish eating.

I had already ordered the check and ended up apologizing to go find the waiter and pay for it.

Finally, as I left, I parted with her at the table and wished her well. There was no way I was risking the discomfort of escorting her to her car. My inherent sense of chivalry was indeed overwhelmed by utter, unapologetic disgust.

Arriving home late at 6:30, I was once again greeted by a “later date” email. In her scathing message to me, Ms. Cash had “accused” me of a series of crimes that clearly aroused her deepest feelings of pain and anger. Among the most particularly amusing was the statement that I was “obviously gay” because I did not see her as attractive.

If she was the last woman on earth, she might have been right about that.

By the way, I finally learned my lesson and left that particular dating site … forever.

4) Cook for your drunk

She was a very pretty kindergarten teacher of Lebanese origin. She was also a total sweetheart. Realizing that her photos consistently got 9.5 seconds on, I rolled the dice and let her come over to my house so I could cook for her.

There were no disappointments. She was exactly my type. And she was already sensitive / sensitive / smiling enough that I knew this was going to go very well.

I mixed him an “Apple-tini”.

“Oh my! This is GOOOD!” she said. Noticing that his glass was empty, I refreshed it for him.

The glass was empty again the next time I looked at her. At that moment, making eye contact with her, she jumped towards me, wrapped her arms around my neck and began to bite me with a giggle.

This girl weighed maybe 110 pounds with a full tank of fuel. (in other words, he probably weighed 110 pounds at the time). So I decided that maybe two glasses would be enough.

However, when I wasn’t paying attention, she had found some raspberry in my stash and started mixing vodka with it.

Ten minutes later, dinner was finished … and it was spectacular, if I may say so.

But she was nowhere to be found.

It was then that I remembered that he had excused himself to go to the bathroom.

I went to check on her and she had vomited (thankfully with tremendously accurate aim) on the toilet, and by that time she had passed out on the floor. What.

Managing to wake her up, her stunned self agreed to let me take her into the bedroom and let her sleep … which she did.

I had dinner alone, watching SportsCenter. The Spurs had lost, no less.

He woke up 8 hours later, found me asleep on the couch, and had made breakfast for me when I woke up. It was a great breakfast. She clearly had the feeling that I was a man she could feel safe with. There was a second date.

Obviously, I learned a few things from my first online dating misadventures. My evening with the cute Lebanese actually happened about six months before I met Emily, so that just proves that you have to be vigilant at all times. Actually, that was probably less of an “online dating disaster.” per se And more a problem of protecting my liquor stash from the repressed school teachers!

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