99 First Dates Ch. 01

For fun, we added a kiosk of six computer desks to make a sort of Internet cyber-café for catering to customers wanting to get some work done. Instead, the on-line gamers usually had all the PC's in constant use every evening and all weekend long. We rearranged things around a little and added another four computer desks and soon every night we had groups scheduling ten-man 'Raids' for their favorite online game and staying until long after midnight. And drinking bottles of Mountain Dew or Jolt Cola like water. With later business hours, if anything, this just lead to us becoming the fun place to visit after clubbing late at night, or even very early in the morning on weekends. Soon, we didn't even bother closing between Friday morning to Monday morning!

We hired a night crew and Farah and I tried to get out the place at a civilized hour. At first for awhile anyway... until I started to learn first hand much more about World of Warcraft and elves and orcs... and Raiding than I ever really wanted to know from our all night weekend customers.

Did I mention that for the first time in my life money was flowing in faster than I could spend it? Different... and rather nice!

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Financially secure now for the first time in my entire life, and just shy of my forty-first birthday, the great challenge of finding a woman that I could enjoy spending the rest of my life with began. One friend bet that I'd find Ms. Right in less than ten dates, but the wiser and more cynical Farah thought it would take me at least thirty. It ended up taking exactly ninety-nine first dates!

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Before I can even to describe this adventure I first need to clarify my original ground rules just a bit. My sources for dateable women were mostly via three separate on-line dating services, a professional 'Introduction' service, and identical ads in the Men-Seeking-Women section of our local alternative newspaper and on Craigslist. In every case I described myself and my interests and wants accurately and provided a recent photograph. The ad read like this:

"40+ WM seeking 30+ F. Disappointed in love long ago and unlikely to be a fast horse out of the starting gate, but patience might be rewarded by a speedy finisher. I am a busy small business owner and a bit old fashioned in too many and numerous ways to count. Financially solvent but not looking to become a sugar daddy. I like books, cats, cheap Italian red wine and anything old and dusty. Hate slimy vegetables, 'Type 'A' over-achievers and anything resembling emotional drama. Am honest, sincere, emotionally stable, non-smoking and happy with where I am in life, and I am (reasonably) height/weight proportional -- I expect the same from you! Uncomfortable with children but might try, for a truly exceptional woman. Sorry, no long walks on the beach -- I sunburn easily."

Once contact was established by either phone or email, I would first suggest (strongly) a casual get-together on the evening of her choice for 'just coffee'. If she then offered dissatisfaction with this plan, I would then instead offer a 'casual dinner' for a weekend evening. In mostly most instances, unless geography was an issue, the coffee date was held at our antique shop/bakery/café. I wanted a bit of home field advantage, plus Farah and our other staff wanted to make their own first impressions of my date. We rarely ever disagreed.

For a coffee date I'd dress in casual Dockers slacks, polo shirt and sneakers. For a restaurant date I'd wear a white shirt and decent dress slacks and shoes. No suit or tie under any circumstances! When I said casual I meant it. I would of course judge her own attire by these same looser standards in all fairness.

Concerning how I graded my date, I created a post-date checklist of items. Did she demand the full dinner treatment rather than just a first casual meeting? Did she sneer at my middle-class restaurant choice (usually my favorite local Italian place)? Did she abuse the serving staff? Did she even pretend to act interested in me? Did she pretend too much? Did she fuss that I wasn't wearing a suit and tie? Did she talk non-stop about vapid topics? Did she discuss her work problems/money problems/ex problems/children problems excessively or even nonstop? Was she stark raving loony? And so forth.

These dates are listed more or less in chronological order, and identified by the single most blatant aspect of her personality. Some traits were shared by many of these women, but in every instance something particularly grabbed my attention about her... usually in a bad way.

Now, let the chronicle of pain and misery begin!

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1. Ms Eager Beaver - She was way too eager. So eager that she had the aura of desperation about her that she plainly wore like a coat for everyone to see. She agreed to my casual 'coffee date', and within the first five minutes had made instant plans for the next month of our relationship. Scary. I broke off the date the moment it was decent to do so and ignored her repeated pleading phone calls for me to call her back, anytime at all - day or night!

This was just supposed to be a casual meeting with no talking about problems or how compatible we are with each other. This is just a first date... it's supposed to be light-hearted and relatively carefree.

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2. Ms. Fattyass - I'm not usually ever rude about other peoples personal appearances, but she wasn't even remotely height/weight semi-proportional. She had sent me a photo of herself that was about a decade old (and over a hundred and fifty pounds lighter than she was today). This massive 300+ pound blob of femininity had demanded the full dinner treatment for our date, but I nipped her feasting plans right in the bud. I was firm but unapologetic; she had patently tried to deceive me by lying (badly) about her appearance, so that she could exploit that old chestnut about her 'beautiful inner self'. Nice try. If she had been honest, I'd have at least fed her. She threw a loud fit and I walked out of the restaurant on her.

I wasn't expecting a Sports Illustrated swimsuit model, but I also don't want a wife or girlfriend that is clinically and morbidly obese... and lies about it.

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3. Ms. Cheapskate -- Another gal who demanded the full wining and dining treatment. She was good looking, pretty smart, and very flirty and an otherwise rather suitable young woman, so we went out a few times over about two weeks. From appearances she likely earned at least three times what I did, and she was apparently used to nothing but the best, and on someone else's wallet. I paid the $150+ dinner checks and then our tabs at the night club next door. Never once did she ever offer to even pay the tip or even once hint about picking up a single round of drinks. I was slightly bemused by her but I got the true message fast when I got the unsubtle hint that she wanted an expensive present for her upcoming birthday.

I'm old fashioned and used to paying for the date, but it's nice when the woman at least offers to pay once in awhile. No, I don't expect you to actually pay on the first date, but after that you should at least reach for your purse occasionally to make the offer, or maybe even cover the tip to the waiter while I cover the cost of the meals, drinks, and whatnot. In Europe while on various antique buying trips, most girls I dated would insist on sharing the bill. It had something to do with personal pride. I guess that's what real emancipation makes out of a woman: They want to show they can pay for their own meals and don't need a spineless sugar daddy that has to pay for female attention.

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4. Ms. Strip-Mall Guidoland Nails -- Farah told me later after this coffee date that she always preferred the term 'ghetto talons' for the insanely long claws that this women possessed. Even a wolverine would have been proud of those claws! She acted fairly hot-to-trot and hinted that we could have another cup of coffee at her place, but I declined.

I didn't want those fake nails anywhere near me, let alone raking my back during sex. She had French tips longer than actual carpentry nails! This screamed 'high maintenance' and I decided to avoid a round two with her.

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5. Ms. Child Drama -- Many of my dates exhibited a good bit of concern about my possible acceptance of their children, but this date sprang this delicate topic by surprise right in the middle of dinner! The 'I have kids' bombshell. Odd, there were none listed in her online dating profile. In her case, with the worry that she was exhibiting about them, there obviously must have been some serious drama going on backstage there, possibly with an ex-husband or baby-daddy who was getting out of prison soon.

After hearing what my brother has gone through with several psycho bitches who had kids by equally unstable other men, I wouldn't ever go down that road except for the lady of my dreams... and this one wasn't it.

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6. Ms. Faux Posh Bit - She dressed up for our casual dinner date like she was a lady of high society. She was appalled at my appearance and gave me a sharp dressing down for my sloppy attire. Then she became unhappy with the normal restaurant menu choices, and she requested the presence of the head chef and special requested that he make her a parmesan-crusted duck breast with balsamic reduction. Then she ordered the most expensive wine on the menu without consulting me. Apparently for her, only the very best of anything would do.

I knew that she was a poseur when she mispronounced half of the words on the French wine bottle and after I had engaged her in a probing discussion about other good wines. She then failed nearly every question I posed to her about places in Europe; I'd been there a few times and knew a few odd things, but she just tried to continue to bullshit that her family had estates in both England, France and Tuscany... but she couldn't name a single airport or town nearby any of them. If I had gotten her faux designer gown onto my bedroom floor, I would have been certain that it was also a fake knockoff.

I also don't like any sorts of breasts with any kind of reduction. I refrained from laughing in her face and tried to enjoy the evening of low comedy, and I lost her phone number afterwards at my earliest convenience.

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7. Ms. Just Low and Outside for a Ball - I have had a few unbelievably awkward dates -- dates that I couldn't wait to get away from, they were such disasters... only to get calls/emails from the ladies asking 'what's next?' This was one of the worst of these. I thought our chemistry during our coffee date was poor and that we really didn't click together as a pair. She thought otherwise. I shrugged and gave her a second try over dinner but it really wasn't any better.

There were other situations where there was really absolutely nothing wrong with the date -- we just had nothing in common and we weren't a good match. I'm sure this goes equal for the women who didn't catch onto my act the first time around either.

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8. Lydia the Tattooed Lady - She was young, wild, uninhibited and actually a decent bit of fun at our coffee date. She was really too young and wild for me but she was such a fun gal that I took her out to dinner the next night. After which we did a few clubs that had live music and we ended up later at my place. She had so many tattoos all over her body that all I got to see was a poorly drawn comic book instead of the naked woman I was looking forward to fucking.

Tats aren't usually a major turnoff for me, but when 95% of your skin is covered in ink I have to wonder exactly what you're rebelling against. I think a few tasteful or pretty tattoos are a perfectly fine way to rebel, I have a very small one myself, but many ladies get extremely defensive when they hear that a lot of guys think they're just over done and gross. When a girl is covered all over with loud and very obvious tats, it sadly says to me that she's probably either a used-up tramp, or a nice girl who has a used-up tramp history. Why permanently mark yourself down a few points with nearly everyone you'd meet? So you can rebel against daddy or feel a little more punk? Sorry, just my opinion. A few would have been fine, but not nearly her whole body.

Ok, the wild monkey sex was really, really good! She loved it in every hole and in every position... and often.

The tats weren't the final deal-breaker -- she was just too young and way too wild for me, and she did have a lot of drama going on in her life with lots of ex-boyfriends waiting for the call to be back on her A-list once again. She had wanted one 'normal' boyfriend not in any alternative punk rock or biker lifestyle and the novelty of my more mundane life wore off fairly fast. We parted friends and she stops by the store occasionally to say 'hi' and refers the odd customer to us, but she's still playing the party road hard and fast and sometimes I feel sorry for her.

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9. Just Plain Fucking Nuts - She was a screeching, mad as a hatter, howling at the moon BPD case that could embarrass hillbillies at a trailer park meth cookout. Oh my God, but she had the crazy! She probably had full-blown Borderline Personality Disorder and I considered myself lucky to escape her after only half an hour with her.

She called the next day to threaten suicide if I didn't take her back again. In her deranged mind I was calling her up non-stop wanted to be with her, but the voice in her head was saying that I needed to prove my love to her by cutting her name into my arm, and to do it right now!

She tried to call me for weeks until I managed to get AT&T to block her phone number from calling mine. Thank God she never learned where I work!

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10. Ms. I have to take this very important call for just a moment - I hate cell phone shenanigans. That has got to be the biggest put-off on a date. If we're having a good conversation and your phone rings and you instantly take the call without even acknowledging the interruption, it says to me that I'm not interesting enough for you to even focus on me for minute or I'm just not worth it for you to even pretend to be considerate. The first time she did it, it was just annoying. By the fourth time I decided that I'd much rather be somewhere else too.

Most women will almost never receive a text/phone call in their entire lives that has to be answered immediately, certainly not the inane 'lol r u 4 ser-e-us?' nonsense that her friends seemed to babble at her all day and all night. It's self-absorbed, egotistical behavior - no excuses about it. She can receive all the calls she wants as long as I'm not sitting there in silence like Joe Jerkoff waiting for her to finish discussing what the high class whores on Sex and the City did on last night's episode with one of her friends.

After this happened the fifth time with the constant phone interruptions, I finally gave up, got up and excused myself to use the bathroom, and when I came back she was still blabbering on the phone. I then just quietly found the waiter and paid our check and told him that anything else she ordered was on her own tab. Then I fucking left -- it was a matter of courtesy.

I set my phone to silent when I'm out on a date and I'd really appreciate the same consideration. Don't talk on your cell phone during a date unless it's a genuine emergency (and the color of someone's nails does not qualify as an emergency). Blood or fire! Your 'oh so very important call' had better involve either the police, EMS or the fire department!

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11. Child Drama Lady #2 -- This mother of the year candidate was so paranoid about my immediate acceptance of her crotch spawn that she brought both of her vile little darlings along with her on our first date at the restaurant so that I could meet them right away. They were a nasty and rather surly pair of brats that obviously already didn't like what they saw in their 'future father' and they were determined to wreck the marriage long before it had the faintest hope of happening.

I faked an emergency at work, paid the restaurant tab and ran, not walked, out of there as fast as my feet would carry me.

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12. Super Cling-Wrap Lady - She was either the most super affectionate huggy-touchy sort of woman that I've ever met or else she was really freaking desperate! She seemed scared that I was going to leave her after just the first date. Kissing on a first date? Heck, she snogged me in the first five minutes! I could hardly keep her in her own chair and out of my lap!

She called me about twenty times during the next three days until I convinced her that I was going to have to suddenly move out of town to take care of my poor ailing mother who lived in the wilds of Nova Scotia.

I just wanted to deal with women that were already more or less already happy with themselves. I'm not going to enjoy time with you if you don't enjoy your own life. Like Bugs Bunny meeting the Abominable Snow Monster, she just wanted to hug me and hold me and pet me and stroke my hair and call me George. Ack!

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13. Ms. God is my Co-Pilot, or Religious Zealot #1 - I never discuss religion on the first date, or usually even the fiftieth. In fact, I don't really have any thoughts about any religion at all. The coffee date started off alright and I was asking her about her weekend plans so that I could fish for some interesting second date ideas. She proceeded to tell me all about her bible school and the next exciting sermon that she just couldn't wait to hear next Sunday. She then revealed her true fundamentalist colors by asking me about abortion and monstrously wicked theory of evolution. Finally she asked me to join her fundamentalist church and by then I had had more than quite enough.

No religion/political/vegan/whatever discussions. Period. Again, this is the first date... I have to like you first before we dive into disagreements. If you start right off with disagreements, I'll likely find you disagreeable.

As Robert Heinlein once wisely said, "Avoid zealots, for they are generally humorless." So very fucking true!

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14. Ms. Bundle of Insecurity - Another coffee date that went horribly off course right from the very start. She was one of those folks who hide her inner insecurity by talking about themselves nearly non-stop. You know the kind; the one's that yap about how great they are, how beautiful they are, or else they'll argue over silly little trivial unimportant things that they should just drop and let go. The crowning touch was when she told me outright that something I had just said was 'stupid'.

Not exactly the way to impress me. That's alright; I didn't impress her either apparently.

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15. Ms. Bowser -- Ok, that was rude, but her on-line picture didn't remotely match the face and body that showed up for our date. Not even vaguely. She'd borrowed a photo of a model from off of the web somewhere to portray the beautiful swan that she saw herself as. Unfortunately, I in turn only saw a rather unattractive woman that displayed many years of hard driving over rather bad roads, with little or no maintenance... and a willingness to deceive.