Effective Questioning Techniques Wait Time Virtual Lesson One-On-One Session My Funniest Online Dating Horror Stories

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My Funniest Online Dating Horror Stories

Yes, yes. It’s true that online dating has worked well for me, in the end. But as I thought about it, I wanted to talk to you about something. It’s not like every single date is a blissful stream of perfection.

Sure, I met a lot of great girls and had a blast over the years… culminating in meeting Emily on Match.com. But eventually, especially in the beginning, I really learned about my share of sometimes funny and sometimes bad situations at night.

Here are the four most memorable:

1) Not What the Doctor Prescribed

Shortly after my divorce in 1992, I received a “spam” message in my inbox that I responded to. Believe it or not, I had never heard of online dating before. This ad claimed that I could meet the girl of my dreams on their site, so I was intrigued.

The next thing you know, I checked how much they were charging and started looking at the pictures of the girls they listed.

Honestly, it’s not the best travel site on the ‘net. Who knew there was a Match.com out there? So inevitably, I found exactly that in a girl who seemed interested in me-a brown-eyed blondie with a friendly smile.

I emailed her, maybe with something lame like “You look beautiful. Maybe we can get along. Do you want to talk?”. Remember, this is Day One for me in the online dating world.

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

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

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

Don’t talk about your medical problems on the 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, he bragged about how he had chronic kidney stone issues and how tough he was to get through it without even flinching today.

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

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

Starting to dig through his purse, he soon produced a small vial of medicine.

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

I wish I was very lucky.

Pressing and twisting the cap without restraining the child, the bottle opened and the contents immediately poured into his hand.

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

With a new French-manicured thumb and forefinger, he made the largest unit from the impressive collection of similar items he held.

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

This woman collects her kidney stones. And he takes them with him 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 MallSweetie

Shortly after the “kidney stone chick”, I met another girl from the same site. She’s a Hispanic cutie with perfect skin and a booty that would make Sir Mix-A-Lot slam on the brakes. He says “sweetie” a lot.

I haven’t learned the part about not taking girls to expensive dinners on first dates, so there’s one of the nicer sushi joints in San Antonio.

He is very nice. He is intelligent and loves to laugh. Above and beyond that, he is a great flirt. He was clearly digging me.

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

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

As he answered, I took a sip of Merlot. And it was then that I learned that all the slapstick “spit takes” you see in old-school comedy sketches are rooted in real truth.

Took everything I saved not to throw up the grape juice all over.

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

Sitting in front of me was a decidedly classy woman, whom I took from a decent house in a nice neighborhood.

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

“No, you fool! LOL! I mean like…you know…strip clubs. The kind that have women.”

Now if you know my style by now, you know that date is as good as it gets.

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

And I asked the inevitable question.

“Yeah, well…my ex handles the day-to-day operations and I handle the books. But he took the ‘interview process’ a little too far, and I can’t trust him anymore. I got the business in the divorce proceedings.”

Before, 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.

It’s probably a good thing I lit a Roman candle. That chick practically attacked me as soon as we left the restaurant. I tried to handle things as best I could with the weather, but let’s just say he was not a happy camper.

When I got home, he had already e-mailed me the nude pictures on his “Adult Friendfinder” profile (which was my first introduction to that particular fact). “This is what you missed. GOOD LUCK!!!” it’s the same line that accompanies the photos.

3) June Carter Cash Or Payment

I should have known better, considering the one pic he attached to his profile was blurry.

And in my heart, I really know better. Suspecting that this particular date might not go well, I invited him to dinner (yes, yes…stubborn isn’t he?) at 5.30p.

I walk into Chili’s or TGIFridays or whatever it is, and immediately get that nauseous feeling that every single online dater experiences at one point or another. In particular, the one where you see a person waiting alone at a table there who vaguely resembles the person you expect to meet like a piece of burnt toast that resembles a very good slice of bread you threw in the toaster and forgot about.

My honest-to-goodness first thought was, “OMG … who replaced the girl with the beautiful smile in the profile with June Carter Cash!”

I’m too much of a “Mr. Nice Guy” to turn around and skip town, so I gather my intestinal fortitude and approach the table.

The conversation was off from the start. He began to make a weak attempt at flirting.

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

He’s dressed in solid black stuff with a lot of stainless steel crap and fringes on it, like a dust-farting legend from “The Grand Ole’ Opry” or something.

The thickness of his Texas accent was only covered by the thickness of his black eyeliner.

Finally, she made her way to the ladies’ room, offering me a blessed respite from the impending regurgitation.

Then the waiter came to the table asking me if I wanted another beer. “NO!” I proclaimed, soon apologizing for the brusque tone he didn’t expect.

“Alright, um…how’s your mom doing?”

“What?”

“Would your mom like another beer?”

Suddenly reminded that one must not take oneself too seriously to get the greatest pleasures in life, I laughed.

I was still recovering when Mrs.

Ordering a small garden salad (after all, who can eat?), my focus turned to saying as little as possible in hopes that he would finish the meal.

I called for the check and excused myself to find the waiter and pay it, already.

Finally, leaving, I parted ways with him at the table and wished him well. There was no way I was going to risk the inconvenience of walking him to his car. My innate sense of genius was actually overwhelmed by sheer anger, unapologetically.

Arriving home at the early hour of 6:30, I was greeted again with a “post date” e-mail. In her harsh message to me, Mrs. Cash “accused” me of a series of offenses that clearly aroused his deep feelings of hurt and anger. Among the funnier things was the assertion that I was “obviously gay” because I failed to find him attractive.

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

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

4) Cook For Your Drunk

She is a very cute kindergarten teacher of Lebanese ethnicity. He is also a total sweetheart. Knowing that her photos always get 9.5s on HotOrNot.com, I rolled the dice and had her come over to my place so I could cook for her.

No disappointments. He is exactly my type. And he’s touchy/feelie/smiley enough that I know it’s good.

I mix him and “Apple-tini”.

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

The next time I looked at him, the glass was empty again. Immediately, making eye contact with him, he jumped on me, wrapped his arms around my neck and started biting me with a giggle.

This chick is probably 110 pounds with a full tank of gas. (in other words, he was probably 110 pounds at the time). So I decided that maybe two drinks would be enough.

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

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

But he was nowhere to be found.

Then I remember him coming out of the bathroom.

I went to check on her and she vomited (thankfully with very precise intent) on the commode, and is currently passed out on the floor. Whatever.

Managing to wake him up, his groggy self agreed that I should take him to the bedroom and put him to sleep… which he did.

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

He woke up 8 hours later, found me sleeping on the couch, and had breakfast ready for me by the time I woke up. It was a great breakfast. She clearly had a feeling that I was a man she felt safe with. Have a second date.

Obviously, I learned a few things from my early online dating misadventures. My night with her Lebanese cutie happened about six months before I met Emily, so that just proves that you have to stay on your toes at all times. Actually, that one might not be much 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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