Online Dating: My Four Funniest Disaster Stories

Online Dating: My Four Funniest Disaster Stories

Yeah, yeah. It’s absolutely true that online dating worked out pretty well for me, ultimately.

But having given it some thought, I wanted to come clean with you about something.

It’s not like every single date was a blissful stream of perfection.

Sure, I met lots of great women and had a blast for several years…culminating in meeting Emily on Match.com.

But along the way, especially at the beginning, I certainly encountered my share of sometimes hilarious and sometimes downright nightmarish situations.

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 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 however much they charged and began looking through the pictures of women they had listed.

To be honest, this was not exactly the most well-traveled site on the ‘net. Who knew there was a Match.com 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 lame like “You seem nice. Maybe we could get along. 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, huh?

Well, one thing led to another, and there we were sitting across the table from one another at dinner. The fact that I shouldn’t have been paying for dinners here has long since been duly noted and is sort of beside the point, so please overlook that for now and read on.

Midway through dinner, she starts talking about her 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 whatever I was eating, she was bragging about how she had chronic kidney stone issues and how tough she was for being able to pass them without even flinching nowadays.

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

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

Already having started digging in her purse, she soon produced a small medicine vial.

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

I should have been so lucky.

Pressing down and twisting the child-proof cap, the bottle opened and the contents were soon poured into her hand.

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

With a freshly French-manicured thumb and forefinger, she produced the largest unit from an impressive collection of similar objects she was holding.

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 do remember there was a second date, believe it or not.

2) Not A Strip Mall, Sweetie

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 “sweetie” a lot.

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

She was terrific. She was intelligent and loved to laugh. Above and beyond that, she was a great flirt. Clearly she was digging me.

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

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

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

It took all I had in reserve not to spew grape juice all over everything.

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

Sitting before me was a decidedly classy woman, who I had picked up from a decent home 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…strip clubs. The kind with girls.”

Now if you know my style at all by now, you already realize the date was as good as over.

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

And I asked the inevitable question.

“Yes, well…my ex ran the day-to-day operations 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.”

It was then, I told her 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 may has well have lit a roman candle. That chick practically attacked me as soon as we left the restaurant. I tried to handle things as best as I knew how at the time, but let’s just say she wasn’t a happy camper.

When I got home, she had already e-mailed me the buck-naked pics from her “Adult Friendfinder” profile (which was my first introduction to that particular reality). “This is what you missed out on. GOOD LUCK!!!” was the only line accompanying the pics.


3) June Carter Cash Or Charge

I should have known better, considering the one pic she had attached to her profile was a blurry one.

And in my heart of hearts, I really did know better. Suspecting this particular date may not go so well, I invited her to dinner (yeah, yeah…hardheaded wasn’t I?) at 5.30p.

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

My honest-to-goodness first thought was, “OMG…who 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.

Conversation was stilted from the very beginning. She began to make a feeble 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 lots of stainless steel crap and fringes on it, like she was some dust-farting 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, she excused herself to the ladies room, offering me a blessed reprieve from impending regurgitation.

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

“OK, um…how about your mom?

“What?”

“Would your mom like another beer?”

Suddenly reminded that one must take oneself much less seriously in order to derive the greatest enjoyment out of life, I burst out laughing.

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

Having ordered a small garden salad (after all, who could eat?), my focus pretty much turned to saying as little as possible in hopes that she would friggin’ finish eating.

I had already called for the check and ended up excusing myself to go find the waiter and pay it, already.

Finally, leaving, I parted ways with her at the table and wished her well. There was no way I was going to risk the awkwardness of walking her to her car. My inherent sense of chivalry was in fact overwhelmed by utter disgust, without apology.

Arriving home at the advanced hour of 6:30, I was greeted once again by a “post date” e-mail. In her vitriolic message to me, Mrs. Cash had “charged” me with a series of offenses that clearly roused her deepest sense of hurt and anger. Among the more particularly hilarious ones was the pronouncement that I was “obviously gay” because I failed to see her as attractive.

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

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


4) Cook For Your Drunk

She was a very cute kindergarten teacher of Lebanese ethnicity. She was also a total sweetheart. Realizing her pics consistently got 9.5s on HotOrNot.com, 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 was going to go really well.

I mixed her an “Apple-tini”.

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

The glass was empty again the next time I looked over at her. Right then, making eye contact with her, she skipped over to me, threw her arms around my neck and started biting me with a giggle.

This chick was perhaps 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 were enough.

But nevertheless, 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 finished…and it was spectacular, if I may say so myself.

But she was nowhere to be found.

It was then I remembered she had excused herself to the bathroom.

I went to check on her and she had vomited (thankfully with tremendously accurate aim) into the commode, and was presently passed out on the floor. Whatever.

Managing to wake her up, her groggy self agreed to let me carry her to the bedroom and let her sleep it off…which she did.

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

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

Obviously, I learned some things from my early online dating misadventures. My evening with the Lebanese cutie actually happened about six months before I met Emily, so that only proves you gotta stay on your toes at all times. Actually, that one was probably less of an “online dating disaster” per se and more of an issue of guarding my liquor stash from pent-up school teachers!


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