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My Funniest Online Dating Horror Stories

Yes, yes. It’s absolutely true that online dating has worked out pretty well for me, in the end. But having thought, I wanted to clear up with you about something. It’s not like every date was a blissful stream of perfection.

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

Here are the four most memorable:

1) Not what the doctor prescribed

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

The next thing you know, I had ponied up as they loaded and started looking through the pictures of the women they had listed.

To be honest, this wasn’t exactly the most visited site on the net. Who knew there was a Match.com out there? So inevitably, I found exactly that one woman I found interesting – a brown-eyed blonde with a friendly smile.

I emailed him back, probably with something lame like “You look great. Maybe we could date. Want to talk?”. Remember, this was the first day for me in the world of online dating.

Call it “beginner’s luck, but he wrote back. Crazy, huh?

Well, one thing led to another, and we were sitting across from each other at dinner. The fact that I shouldn’t have paid for dinners here has long been noted and is sort of the point, so please ignore that for now and read on.

In the middle of dinner, he starts talking about his medical problems.

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

Between bites of everything he was eating, he was bragging about how he had chronic kidney stone problems and how hard it was to be able to get through without even tripping today.

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

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

Already starting to dig into his bag, he soon produced a small vial of medicine.

I thought to myself, “This boy must be joking. I believe him, already. He shouldn’t prove his case by showing his prescription.”

I had to be so lucky.

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

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

With a freshly manicured thumb and forefinger in French, he produced the largest unit from an impressive collection of similar objects he held.

Yes. It was the biggest 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 a second date, believe it or not.

2) Not a Strip Mallsweetness

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

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

She was fantastic. He was smart and loved to laugh. Above and beyond, he was a great flirt. He was clearly 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 ‘autonomous’. What exactly do you do?”, I asked.

As she answered, I took a sip of Merlot. And it was right then that I discovered that all those slapstick “sput takes” you see on old-school comedy sketches are rooted in factual reality.

Took everything I had in reserve so I didn’t spew grape juice all over it.

“I have a chain of strip clubs, Sweetie,” he announced matter-of-factly.

Sitting in front of me was a decidedly classy woman, who I had taken from a decent home in a nice neighborhood.

“I mean, like a streak mall… right … with nail salons, a tanning salon and a Chinese restaurant.”

“No, stupid! LOL! I mean like…you know…creep clubs. The kind with little girls.”

Now if you know my style at all, by now, you already understand that the date was like over.

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

And I asked the inevitable question.

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

It was then, I told him the truth.

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

Uh oh.

I might as well have lit a roman candle. That chick practically attacked me as soon as we left the restaurant. I tried to handle things the way I knew how at the time, but let’s just say I wasn’t a happy camper.

When I got home, he had already emailed me the nude photos from his “Adult Friendfinder” profile (which was my first introduction to that particular reality). “This is what you’ve been missing. Good luck!!!” it was the only line accompanying the photos.

3) June Carter Cash Or Charge

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

And in my heart of hearts, I really knew better. Suspecting that this particular date might not go so well, I invited her to dinner (yes, yes…hard wasn’t it?) at 5.30p.

I walked into Chili’s or TGIFridays or whatever it was, and immediately got that nauseating feeling that every online single experiences at one point or another. In particular, the one where you see someone just waiting at a table there, who vaguely resembles the person you’ve been waiting to meet as much as a piece of burnt toast resembles the perfectly good slice of bread you threw at the toaster is forgotten.

My first honest-to-goodness thought was, “OMG…that replaced the woman with the nice smile in the profile with June Carter Cash!”

I was too much of a “Mr. Nice Guy” to turn tail and skip town immediately, so I gathered my intestinal fortitude and approached the table.

The conversation was strained from the start. She began to make a weak attempt at flirting.

The woman was at least 55 years old. And not a very attractive 55 year old at that.

She was dressed in solid black stuff with a shitload of stainless steel and fringe on it, like she was a dust legend from “The Grand Ole’ Opry” or something.

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

Finally, he excused himself to the ladies’ room, offering me a blessed reprieve from impending regurgitation.

It was then that the waiter came to the table asking me if I wanted another beer. “NO!” I proclaimed, quickly apologizing for the abrupt tone that neither he nor I had anticipated.

“Ok, um… what about your mom?

“Which one?”

“Would your mother like another beer?”

Suddenly, reminded that one must take oneself much less seriously in order to have the greatest fun in 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 that?), my focus almost turned to saying as little as possible in hopes that she would finish eating.

I had already called for the check and ended up apologizing to go find the server and pay, already.

Finally, leaving, I shared with her at the table and wished her well. There was no way I was going to risk the embarrassment of driving him to his car. My inherent sense of chivalry was in fact overwhelmed by utter, unapologetic disgust.

Arriving home at the late hour of 6:30, I was once again greeted by a “post date” email. In her vitriolic message to me, Ms. Cash had “accused” me with a series of insults that clearly evoked her deepest sense of hurt and anger. Among the most particularly amusing was the claim that she was “obviously gay” because I failed to find her attractive.

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

Incidentally, I finally learned my lesson and leave the particular dating site … forever.

4) Cook For Your Drunk

She was a very cute kindergarten teacher of Lebanese ethnicity. It was also total love. Realizing that her photos still got 9.5s on HotOrNot.com, I rolled the dice and let her come over to my place so I could cook for her.

There were no disappointments. He was exactly my type. And he was already touchy/feelie/smiley enough that I knew this was going to be really good.

I mixed it an “Apple-tini”.

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

The glass was empty again the next time I looked at it. Then, making eye contact with her, she jumped towards me, threw her arms around my neck and started biting me with a giggle.

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

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

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

But there was nothing to be found.

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

I went to check on her and she had vomited (fortunately with a tremendously accurate aim) in the commode, and she passed out on the floor. Whatever.

Managing to wake her up, her groggy agreed to let me take her to the room and let her sleep outside…which she did.

I ate 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 me breakfast when I woke up. It was a great breakfast. She clearly had a sense that I was a man with whom she could feel safe. There was a second date.

Obviously, I learned a few things from my first online dating misadventures. My night with the Lebanese cutie actually happened about six months before I met Emily, so it just proves that you have to be on your toes at all times. Actually, that was probably less of an “online dating disaster” per se and more of a problem guarding my liquor stash from pent-up school teachers!

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