My funniest online dating horror stories

Yes Yes. It is absolutely true that online dating ultimately worked pretty well for me. But after thinking about it, I’d come clean with you about something. It’s not like every single date was a blissful stream of perfection.

Sure, I met lots of amazing women and had an explosion for several years … and culminated with meeting Emily on But along the way, especially in the beginning, I certainly met my share of sometimes funny and sometimes downright nightmares.

Here are the four most memorable ones:

1) Not what the doctor prescribed

Very shortly after my divorce in 1992, I received a “spam” message in my inbox that I actually responded to. Believe it or not, I had not even heard of online dating before. This ad claimed that I could meet the woman of my dreams on their site so I was intrigued.

The next thing you know I had ponyed up, no matter how much they charged and started looking through the pictures of women they had listed.

To be honest, this was not exactly the most traveled site on the web. Who knew there was a out there? So inevitably I found exactly one woman who seemed interesting to me – a brown-eyed blondie with a friendly smile.

I emailed her, probably with something limp like “You seem cute. Maybe we could get together. Would you like to talk?”. Remember, this was day one for me in the online dating world.

Call it “beginner’s luck, but she wrote back. Crazy, right?

One thing led to the other and there we sat across the table from each other at dinner. The fact that I should not have paid for dinners here has long been duly noted and is sort of beside the point, so disregard it for now and read on.

Midway through dinner, she starts talking about her medical issues.

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

Between bites of what I ate, she boasted about how she had chronic kidney stone problems and how tough she was to pass them without even flinching today.

Unfortunately, she took my leisurely attempt to divert the discussion like disbelief.

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

Even after starting digging in her bag, she soon produced a small vial of medicine.

I thought to myself, “This chicken needs to be playing. I believe in her already. She doesn’t have to prove her case by showing me her prescription.”

I should have been so lucky.

Pushing down and twisting the childproof cap opened the bottle and the contents were quickly poured into her hand.

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

With a freshly-manicured thumb and index finger, she produced the largest unit from an impressive collection of similar items she had.

Yes. It was the largest kidney stone she had ever passed.

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

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

2) Not a strip Mall, Sweetie

Not long after the “kidney stone” I met another woman from the same place. She was a Latin American sweet with perfect skin and a booty that would have made Sir Mix-A-Lot slap on the brakes. She said “sweet” a lot.

I hadn’t learned the part about not taking women to expensive dinners on first dates yet, so there was one of the nicer sushi joints in San Antonio.

She was amazing. She was intelligent and loved to laugh. On top of that, she was a great flirt. She obviously digs me.

We had ordered two glasses of red wine and the conversation turned to what she was doing to live.

“So you said you were ‘independent’. What exactly are you doing?”, I asked.

While she was responding, I took a sip of Merlot. And it was just then that I discovered that all those slapstick “spit-takes” you see on old-school comedy sketches are rooted in actual reality.

It took everything I had in the reserve not to spray grape juice over everything.

“I run a chain of strip clubs, Sweetie,” she had announced.

Last in front of me was a decidedly classic woman who I had picked up from a decent home in a nice neighborhood.

“You mean, like a strip shopping mall… straight … with nail salons, a tanning salon and a Chinese restaurant. “

“No, silly! LOL! I mean like … you know … strip clubs. That kind of thing girls. “

Now, if you know my style at all, you already know that the date was as good as past.

Still, it was like a train wreck. I couldn’t look away.

And I asked the inevitable question.

“Yeah, yeah … my ex ran the daily operation, and I pretty much handled the books. But he let the ‘interview process’ go a little too far too often and I couldn’t trust him anymore. I got the business in the divorce settlement.”

That’s when I told her the truth.

“I’ve never been to one of these places in my life and I see no reason to start now.”

Oh, oh.

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

By the time I got home, she had already sent me the nude photos from her “Adult Friendfinder” profile (which was my first introduction to that particular reality). “This is what you missed. GOOD LUCK !!!” was the only line that followed the pictures.

3) June Carter cash or fee

I should have known better, considering that the image she had attached to her profile was blurry.

And in my heart, I really knew better. Suspicion of this particular date might not go so well, I invited her to dinner (yes, yes … hard hair wasn’t I?) At. 5.30.

I went into Chili’s or TGIFridays or whatever, and immediately got the nauseous feeling that every single online dater experiences at some point. Specifically, the one where you see someone waiting alone at a table over there who vaguely resembles the person you expected to meet about as much as a slice of roasted toast looks like the perfectly good bread slice you threw in the toaster and forgot about it.

My first honesty to goodness was thinking first: “OMG … that replaced the woman with the beautiful smile in the profile with June Carter Cash!”

I was too much of a “Mr. Nice Guy” to turn his tail and skip the city right away, so I gathered my gut strength and approached the table.

The conversation was silenced from the beginning. She began to make a feeble attempt to flirt.

The woman was at least 55 years old. And not a particularly attractive 55-year-old at the time.

She was dressed in solid, black stuff with lots of stainless steel crap and fringes on it, like she was a dust-busting legend from “The Grand Ole ‘Opry” or something.

The thickness of her Texas accent was only eclipsed by the thickness of her black eyeliner.

Eventually, she apologized to the women’s room and offered me a blessed postponement of impending regurgitation.

That’s when the waiter came to the table and asked me if I wanted another beer. “NO!” I proclaimed and soon apologized for the brusque tone neither he nor I expected.

“OK, um … what about your mother?


“Does your mother want a different beer?”

Suddenly reminded that one must take much less seriously to get the greatest joy out of life, I burst out laughing.

I was still recovering when Mrs. Cash returned to the table.

After ordering a small garden salad (after all, who could eat?), My focus pretty much turned to say as little as possible in the hope that she would friggin ‘finish eating.

I had already called for the check and ended up apologizing to myself for finding the waiter and paying it already.

Eventually, I parted ways with her at the table and wished her luck. There was no way I would risk the discomfort of walking her to her car. In fact, my inherent sense of chivalry was overwhelmed by complete disgust without apology.

When I arrived home in the advanced hour at. At 6:30 am, I was once again greeted by a “post date” email. In her vitriolic message to me, Mrs. Cash had “accused” me of a series of offenses that clearly aroused her deepest sense of hurt and anger. Among the more hilarious fun was the statement that I was “openly gay” because I couldn’t see her as attractive.

We are the last woman on earth, she may have been right about that.

Incidentally, I finally learned my lesson and ended that particular dating site … forever.

4) Cook for your drunk

She was a very sweet kindergarten teacher with Lebanese ethnicity. She was also a total boyfriend. Once I realized that her photos consistently got 9.5s on, I threw the dice and let her come to my place so I could cook for her.

There were no disappointments. She was exactly my type. And she was already being touchy / feelie / smiley enough that I knew this would go really well.

I mixed her an “Apple tini”.

“Oh my! This is GOOOD!” she said. When I noticed that her glass was empty, I updated it for her.

The glass was empty again the next time I looked at her. Just as she made eye contact with her, she jumped over to me, threw her arms around my neck and started biting me with a giggle.

This chicken was maybe 110 pounds with a full tank of fuel. (in other words, she was probably 110 pounds at that moment). So I decided maybe two drinks was enough.

But nonetheless, when I wasn’t paying attention, she had found some raspberry stuff in my stash and had begun mixing vodka with it.

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

But she was nowhere to be found.

That’s when I remembered she had excused herself in the bathroom.

I went to check on her and she had thrown (thankfully with incredibly accurate targets) into the dresser and was currently sent out to the floor. No matter what.

When she managed to wake her, her groggy self accepted to let me carry her to the bedroom and let her sleep it off … which she did.

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

She woke up 8 hours later, found me sleeping on the couch and had prepared me breakfast when I woke up. It was a lovely breakfast. She obviously had the feeling that I was a man with whom she could feel comfortable. There was another date.

Obviously, I learned some things from my early online dating misadventures. My night out with the Lebanese sweet actually happened about six months before I met Emily, so it just goes to show that you must always be on your toes. In fact, it was probably less of a “disaster online” in itself and more of a matter of protecting my liquor stash from suspended school teachers!