Best Worst Dates Ever

It’s Valentine’s Day, single and flaked out on the couch, what better time to reminisce about that dating thing I vaguely remember doing.

I don’t date often, so I usually date well, and first dates are generally a good time. Like that fella I met for a movie and we hit it off so well we decided to go out for dinner afterwards. While driving down McLeod Trail looking for a place to eat, we were so caught up in conversation and banter we reached the city limits before we remembered we were looking for a restaurant.

Or that guy I liked so much I got up early for a date that started in the morning (and ended up going for 15hrs). A day that started particularly early for me so I could make sure I had time to shave my legs. Something of importance as he had asked me out for lunch the week previous and as we sat in the park eating take-out chinese and “lunch” moved into it’s third hour, I started to wonder: “Hey, is this a date? It kinda feels like a date.” Then I look down at my cross-legged shins in the grass and thought: “Well, I hope it’s not a date, ‘cause I totally need to shave my legs.”

But more fun to remember are the dates that didn’t go well. Like the guy I met for a walk in the park. Nice afternoon, but aside from kicking up a bit of dust, the earth did not move. Partially because I’m a bit of a shit, and partially ‘cause I really didn’t know for sure, as the date wrapped up I asked him what he thought – in fairness to me (i.e. I’m not a total shit), the question was precipitated by him previously saying he could tell in less than 5 minutes if there was gonna be chemistry, so I didn’t think it was totally off the mark to just ask. I was actually surprised when he said “Yeah, I’d like to see you again.” (the fact that in my head I said “REALLY?” should have been a clue as to how much chemistry I was reading). I was then secondarily surprised to not hear from him again. And even more surprised to run into him later and get sucked into one of the longest, most awkward conversations I’ve ever been in – he just would not stop talking to me (and he clearly didn’t really want to be talking to me), no matter how many outs I gave him. Awkward! An awkwardness highlighted by having to look over his shoulder as  my friend tried to act like she was shopping, all the while shaking in silent laughter. Really hard for me to keep a straight face through that one.

You’d think that would be the end of one of my best awkward stories ever, but this was destined to become the Never Ending Awkward Story. A year later, another friend (who had never met him) was shopping where he worked and went to ask him a question and well, the tale is best told through a rough re-creation of her internal dialog at the time:

“Hey, I think this is that guy Valerie was talking about.” [being as this was one of my best awkward stories, I didn’t hesitate to tell it] “Oh, I faltered over my question – distracted, remembering that awkward story.” “Oh, he noticed I got tongue tied… and just looked me up and down.” “Oh God, I think he’s checking me out! He must think I’m into him, getting all flustered around him” “Now I really can’t remember what I was going to ask him” “Wow, this is really awkward…”

Awkward, and a beautiful awkwardness that just keeps spreading, but in the worst date ever category, first runner up would have to go waaaay back to when I was sixteen, at one of those drunken house parties where none of us had enough sense to know how to drink. In the back seat with my beau to be, getting a ride back to my place, my darling date proceeds to vomit…into a cardboard box…which, naturally, leaked. This delightful experience is only my second worst date however, ‘cause with a bit of coffee…and mouthwash, it was retrieved from utter disaster.

My worst date ever also has it’s origins in drunken house parties, much later in time, when most people had learned how to drink. After having met this one particular guy at several parties in a row, we finally ended up one on one, outside the party group. We went hiking. As a novice hiker, I wasn’t keeping the pace he would have set; he did not make a lot of effort to disguise his annoyance at this – a fact that did not endear him to me whatsoever. So we had a very lonnnng, painful, awkward date thoroughly NOT enjoying each other’s company (though the scenery was lovely).

Sadly, the highlight of that outing, for me anyway, was watching him walk through long grass and immediately break out in hives (allergies – guess he wasn’t so rugged after all). As much as I was enjoying a bit of karmic kickback, I did manage to refrain from giving him a hearty Simpsons “Har! Har!” and was even able to show a bit of concern for his wellbeing, and was glad to find he had an inhaler with him.

The best part of this worst date ever would be that the whole time we were trudging through the woods in grumbling silence, I wanted to grab him by the sleeve, look into his eyes and say: “But…but…don’t you remember?…How completely captivating I am…when you’re drunk.”

And that, would be my best worst date ever story.

So, those of you not busy with the flush of love on this sainted day, let’s hear your stories…best dates, worst dates, Valentine horror stories. What else were you gonna do today?

p.s. Sorry, no images for this article, my photo collection is – not surprisingly – short on pictures from first dates. But hey, wouldn’t that be a fun first date: “Nice to meet you, let’s go to Sears for a photo shoot. Dibs on the 8×10! You can have the wallet sized.” Ah…awkwardness immortalized in film. Any takers? Only $19.95.

If you were amused by this, you’re gonna love Why I’m Still Single.

One thought on “Best Worst Dates Ever

  1. I haven’t had much practice on the dating field. I can’t remember having any really bad dates. The worse one I can remember is being invited out to a relatively expensive restaurant. After eating our meal my date realized that he forgot his wallet. Not expecting to have to pay I hadn’t brought very much cash and I didn’t have a credit card at the time. My date said to wait for him and he would go back to his residence to get his wallet. The second problem was that we had taken the bus to the restaurant and it took forever for my date to get a bus back to the University, get his wallet and get a bus back. While I waited the waiter kept his kind eye on me. He must have realized what happened and he kept asking me if I needed anything. I drank a lot of glasses of water that night.

    My best date was almost like a dream. My date invited me to the opening of a Gauguin exhibit. It was the first official gallery opening that I’d ever been to. We were greeted at the door with a lei of simple orchids since most of the paintings were from Gauguin’s Tahiti period. My date was my equal in genuine interest in art and we spent a pleasant evening gazing, admiring and talking about the art. Neither he nor I wanted the evening to end so he asked if I would like to go for tea. He said he knew the perfect place so I said sure, thinking it was just around the corner from the gallery. We ended up walking about 2 miles before we got to this little French restaurant where he treated me to my first crepe. Julia Child would have been in heaven, all that cream, chocolate, and luscious fruit. You’d think that would be a fitting end to a lovely evening but we decided to keep walking that night and we must have walked another 3 miles while we talked. About a week after the date he sent me a very romantic letter describing the street lights like stars that lit our path, and me being like an angel. Too bad I was engaged to someone else at the time. Misssed opportunities!


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