March 23rd, 2006


The End is Nigh

The time has come. I just picked up my second internet stalker in the span of a couple months, so I've decided that after a long and glorious run on the internet dating scene, it is time to turn in the uhhhhhh... keyboard? To commemorate this fact, I've decided to give an account of my five worst on-line dating experiences. My criteria are as follows:

1. I had to actually go on a date with the person. I've had some crazy interactions with people via phone and e-mail (such as my stalkers), but to qualify for this list we had to meet in person.

2. The "badness" of the date had to somehow be a product of the actual date. In other words, I'm not going to whine about rejection - this is about bad dates not hurt feelings. This also rules out the woman who told me she didn't understand fractions (it wasn't just that she was bad at math or something, if you said that you had a third of a cake she would have no idea what you were talking about) since this didn't really affect the date itself (since we didn't split the check in half or anything).

3. It had to be a bad date, not a dud. So, the many times I met someone who was perfectly nice but couldn't keep up with my sparkling wit and charm don't count - here I'm celebrating dates that were over the top; dates that are memorable for all the wrong reasons.

So there you have it. For the sake of privacy I will refer to each and every woman as "Jill." Why Jill? Why not? The countdown will begin with the 5th worst date and will then follow a downward spiral that will culminate in my worst date ever (and yes, following in the fine tradition of VH1, the list does have a twist).

Stay tuned for #5 - "You Owe Me A Buck Fifty!"
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# 5 (of 5) - You Owe Me A Buck Fifty!

My 5th worst internet date:

I should have known things were bad the moment I realized Jill lived outside of the 610 loop (outside the loop = weirdos). But she wasn't just outside the loop, she was waaaaaay outside the loop and, being the gentleman that I am, I offered to drive to her rather than meet somewhere in the middle since she had a two-year-old son and had to have a babysitter.

I had also told her that I don't drink coffee or wake up before noon, yet we agreed to meet at a Starbucks at noon because that's when she could get a babysitter (again, always the gentleman). So, I get up early, drive into the suburban nightmare of Not-Inside-the-Loop, Texas and, despite all of this manage to arrive on time. Jill was ten minutes late. But so far, all is forgivable.

So she finally arrives and when she gets out of her Range Rover is wearing borderline MOM jeans (you know - a little too much abdomen, a little too much flair in the hips, a little too much taper in the ankles, a little too 80s to be worn any time after 1989) and a blouse that is to the upper body what the MOM jeans are to the lower body (a little too much shoulder, not quite enough arm, not quite hot pink enough to actually be hot pink, but hot pink enough to think "I bet she'd be embarrassed if she realized she bought something that's almost hot pink").

Then came what turned out to be the critical moment of the date. We got in line where I usually make a point of being ahead of my date so I can order what I want and then say "...and whatever she wants" and then pay without that awkward moment of trying to figure out who is going to pay for what. Unfortunately, as we were getting close to the front of the line another line opened and that guy caught her eye before mine, so she ordered before me and used the same trick - she finished her order and then said "...and whatever he wants" (which was just a bottle of water), and then paid before I had a chance to object or attempt to pay myself. I made the obligatory reach for my wallet but by that time she had already handed over her credit card and said "don't worry about it" so I just thanked her and figured she probably didn't mind since I had driven all the way out there to drink water at a coffee shop. Now anyone who knows me knows that I never have a problem paying - in fact, I often offer to pay even when I really don't have to or shouldn't - sometimes my complete lack of financial responsibility manifests itself as reckless generosity. In this case things just happened quickly and since the whole bill was less than $5 and my part of it was less than $2 I just figured it wasn't a big deal.

So, the date proceeded, and was the quintessential dud. In fact, had that been the whole story, Jill would not have qualified for the list (see criterion #3 of "The End is Nigh"). When it was over I drove all the way back to the Loop (a.k.a. Where the Cool Kids Live) and took a much needed nap (who goes on a date at noon?).

A little over a week later, after no communication with her whatsoever (I certainly had no plans to call), I recieve the following e-mail (as closesly as I can remember it):


You seem like a nice guy in general, but you have a lot to learn about dating. You should never let the woman pay, even if she offers. I couldn't believe it! It was such a turnoff! Anyway, good luck with your dissertation.


Now, it might very well be true that I have a lot to learn about dating - I'm still single, after all. But I know a lot of women feel weird when a guy insists on paying, especially when the circumstances would make it confusing and a hassle to do so. I had reached for my wallet and she told me not to worry about it, so I assumed she was a mature adult who wouldn't offer to pay for my $1.50 bottle of water unless she was really okay with springing for a $1.50 bottle of water, especially after I had gone to such lengths to accomodate her up to that point (I was outside the Loop at noon for god's sake!).

Furthermore, why wait over a week and then send such a spiteful e-mail? I've had plenty of dates in which the woman did something that turned me off and I didn't send an angry e-mail - I just let it go. Maybe she thought she was doing me a favor - offering me some helpful advice. What she was really doing was earning the #5 spot on my "Worst Dates Ever" list (I realize this wasn't THAT bad, which is why it's only #5 - they get worse, much, much worse).

Stay tuned for #4 - "The World's Most Boring Woman."
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