My funniest online dating horror stories

Yes Yes. It’s absolutely true that ultimately online dating worked pretty well for me. But after thinking about it for a bit, I wanted to clear something up for you. It’s not like every date is a wonderful stream of perfection.

Sure, I’ve met a lot of great women and had a great time over a number of years… culminating in meeting Emily on But along the way, especially early on, I certainly found my share of situations sometimes hilarious and sometimes downright nightmarish.

Here are the four most memorable:

1) Not what the doctor ordered

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

The next thing I knew I had spent everything they charged and I started looking at the photos 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 out there? So inevitably, I found exactly one woman I found interesting, a brown-eyed blonde with a friendly smile.

I sent him an email, probably with something silly like, “You seem nice. Maybe we can 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 shot back. Crazy huh?

Well, one thing led to another, and there we were sitting at each other’s table during dinner. The fact that you shouldn’t have been paying for dinners here has long since been duly noted and besides the point, so forget about it for now and read on.

Halfway through dinner, he begins to talk 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 whatever she ate, she would brag about how she had chronic kidney stone problems and how strong she was to be able to pass them without even flinching these days.

Unfortunately, she mistook my casual attempt to entertain the discussion for disbelief.

“Don’t you think I have kidney stones? Here… look…”

Having started to rummage through her bag, she soon pulled out a small vial of medicine.

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

I should have been so lucky.

By pressing and twisting the child-resistant cap, the bottle was opened and the contents soon poured into his hand.

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

With a freshly severed thumb and forefinger, he pulled out the largest unit of an impressive collection of similar objects he held.

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

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

I don’t remember what I said or did, really. But I do remember that there was a second date, believe it or not.

2) It’s not a strip MallDear

Not long after the “kidney stone girl” I met another woman from the same site. She was a Hispanic cutie with flawless skin and booty that would have made Sir Mix-A-Lot slam on the brakes. She said “honey” many times.

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

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

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

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

As she answered, I took a sip of the Merlot. And it was right then that I discovered that all those antics you see in old school sketch comedy have their roots in objective reality.

It took everything I had in reserve to keep from spilling grape juice everywhere.

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

Sitting across from me was a decidedly elegant woman, whom I’d picked up at a decent house in a nice neighborhood.

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

“No dummy! LOL! I mean…you know…get naked.” clubs. the guy with girls.”

Now, if you already know my style, you will have already realized that the date was already over.

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

And I asked him the inevitable question.

“Yeah, well…my ex ran the day-to-day operations and I pretty much ran the books. But he let the ‘interview process’ go on too often, and I couldn’t trust him anymore. I got the business on the deal.” divorce”.

It was then that I told him the truth.

“I’ve never been to one of those places in my life, and I don’t see any reason to start now.”

Uh oh.

You may have read a roman candle. That girl practically attacked me as soon as we left the restaurant. I tried to handle things the best I could at the time, but let’s just say she wasn’t a happy camper.

By the time I got home, she had already emailed 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 accompanied the photos.

3) June Carter Cash Gold Charge

She should have known better, considering the only photo she’d 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 (yeah, yeah… stubborn, right?) at 5:30 pm.

I walked into Chili’s or TGIFridays or whatever, and immediately got that queasy feeling all online daters get at one point or another. Specifically, the one where you see someone waiting alone at a table who vaguely resembles the person you were hoping to meet about as much as burnt toast resembles the perfectly good slice of bread you tossed in the toaster and forgot about.

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

I was too “Mr. Nice Guy” to turn around and leave town right away, so I gathered up my gut strength and walked over to the table.

The conversation was forced from the beginning. She began to make a feeble attempt at flirtation.

The woman was at least 55 years old. And he’s not a very attractive 55-year-old man.

She was dressed in solid black with a bunch of stainless steel shit and fringe, like she was some dust-farting legend from “The Grand Ole’ Opry” or something.

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

Finally, she excused herself to go to the ladies’ room, offering me a blessed reprieve from the impending regurgitation.

That’s when the waiter came over to the table asking if I wanted another beer. “NO!” I proclaimed, promptly apologizing for the abrupt tone that neither he nor I had anticipated.

“Okay, um…what about your mom?


“Would your mom like another beer?”

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

I was still recovering when Mrs. Cash came back to the table.

Having ordered a small salad (after all, who could eat it?), my attention was drawn to saying as little as possible in the hope that I would finish eating.

I had already asked for the bill and ended up apologizing to go find the waiter and pay for it, now.

Finally leaving, I shared manners 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 with utter, unapologetic disgust.

Arriving home at the late hour of 6:30, I was once again greeted by a “date published” email. In her vitriolic message to me, Mrs. Cash had “accused” me of a series of offenses that clearly aroused the deepest feelings of grief and anger in her. Among the most particularly amusing was the pronouncement that I was “obviously gay” because I didn’t find her attractive.

If she was the last woman on earth, she might have been 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 cute kindergarten teacher of Lebanese ethnicity. She was also a total sweetheart. Realizing that photos of her always got 9.5 seconds on, I rolled the dice on her and let her come over to my house so I could cook for her.

There were no disappointments. She was exactly my type. And she was already being delicate/emotional/smiling enough to know that this was going to turn out very well.

I mixed him an “apple-tini.”

“Oh, 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. At that point, making eye contact with her, she jumped at me, threw her arms around her neck, and began to bite me with a giggle.

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

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

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

But she was nowhere to be found.

It was then that I remembered that he had excused himself to go to the bathroom.

I went to check on her and she had thrown up (thankfully with tremendously accurate aim) in the toilet, and was currently passed out on the floor. Whatever.

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

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

He woke up 8 hours later to find me asleep on the couch and had made me breakfast when I woke up. It was a great breakfast. She clearly had the feeling that I was a man she could feel safe with. There was a second date.

Obviously, I learned a few things from my early misadventures with online dating. My evening with the Lebanese cutie actually happened about six months before I met Emily, so that just proves you have to be vigilant at all times. Actually, that was probably less of an “online dating disaster” per se and more a matter of protecting my stash of liquor from the repressed schoolteachers!