What Bread Can I Give My 6 Month Old Baby My Funniest Online Dating Horror Stories

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My Funniest Online Dating Horror Stories

Yes, yes. It’s absolutely true that online dating was good enough for me, after all. But after thinking about it, I wanted to come clean 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 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:

1) Not What The Doctor Prescribed

Very shortly after my divorce in 1992, I received a “spam” message in my inbox, which I actually responded to. Believe it or not, I had never even heard of online dating before. This ad claimed I could meet the woman of my dreams on their website, so I was intrigued.

The next thing you know, I came up with whatever they were charging and started looking through the pictures of women they had listed.

Admittedly, this wasn’t exactly the most well-traveled site on the ‘net. Who knew there was a Match.com out there? So inevitably, I found it right one a woman who seemed interesting to me – a brown-eyed blonde 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 world of online dating.

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 each other at dinner. The fact that I shouldn’t have paid for dinners here has long been established and is kind of beside the point, so please ignore that for now and read on.

Halfway 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 bragged about how she had chronic kidney stone problems and how hard it was for her to be able to pass them without even flinching these days.

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

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

Already starting to dig into her purse, she soon produced a small medicine vial.

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

I should be so lucky.

Squeezing and twisting the child-resistant cap, the bottle opened and the contents were soon poured into her hand.

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

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

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

This woman collected her kidney stones. And she took them everywhere with her, 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) No Streak Shopping centerdarling

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 hit the brakes. She said “sweetie” a lot.

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

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

We 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 drank Merlot. And that’s when I discovered that all those slapstick “spits” you see in old-school comedy sketches are rooted in actual reality.

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

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

Sitting in front of me was a decidedly glamorous woman whom I had taken from a decent home in a nice neighborhood.

“You mean, like a streak shopping center…right…with the nail salons, tanning salon and Chinese restaurant.”

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

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

However, 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 pretty much handled the books. But he let the ‘interview process’ go a little 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.”

Oh oh

I may have already lit a roman candle. That chick almost 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 was not a happy camper.

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

3) June Carter Cash Or Charge

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

And in my heart, I really knew better. Suspecting that this particular date might not go so well, I invited her to dinner (yes, yes…hard headed right?) at 5.30pm.

I walked into Chili’s or TGIFridays or whatever it was, and immediately got that nauseous feeling that every single internet 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’ve been waiting to meet, as much as a piece of burnt toast resembles the perfectly good slice of bread you threw in the toaster and about forgot

My honest-to-goodness first thought was, “OMG … who 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 tail and skip town right away, so I gathered my intestinal fortitude and approached the table.

Conversation was interrupted 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 a lot of stainless steel crap and fringe on it, like she was some dust fart legend from “The Grand Ole’ Opry” or something.

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

Finally, she excused herself to the women’s room, offering me blessed reprieve from imminent 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 that neither he nor I had anticipated.

“Okay, um…how about your mom?


“Would your mom like another beer?”

Suddenly reminded that you have to take yourself a lot less seriously to get the most enjoyment 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 almost turned to saying as little as possible in the hope that she would finish her meal.

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

Finally, leaving, I parted 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 actually overwhelmed by utter disgust, without apology.

Arriving home at the early hour of 6:30, I was greeted again with an “overdue” email. In her vitriolic message to me, Ms. Cash “accused” me of a series of offenses that clearly evoked her deepest sense of hurt and anger. Among the more particularly hilarious was the statement that I was “obviously gay” because I couldn’t see her as attractive.

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

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

4) Cook For Your Drunk

She was a very beautiful kindergarten teacher of Lebanese ethnicity. She was also a total sweetheart. Noticing that her photos were consistently getting 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. She was exactly my type. And she was already touching/feeling/smiling enough that I knew this was going to be really good.

I mixed her “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 her. Just then, making eye contact with her, she jumped over to me, threw her arms around my neck and started biting me with a laugh.

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

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

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

But she was nowhere to be found.

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

I went to check on her and she vomited (luckily with extremely precise aim) into the dresser, and presently passed out on the floor. Whatever.

Succeeding in waking her up, her horrible self agreed to let me carry her to the bedroom and let her sleep it out…which she did.

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

She woke up 8 hours later, found me sleeping on the couch, and made me breakfast when I woke up. It was a great breakfast. She clearly felt that I was a man with whom she could feel safe. It was a second date.

Obviously, I learned a few things from my early online dating misadventures. My evening with the Lebanese sweetheart actually happened about six months before I met Emily, so that just goes to show that you have to stay on your toes at all times. Actually, that was probably less of an “online dating disaster” by itself and more of a matter of guarding my drink reserve from stuffy school teachers!

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