We all know that Valentine’s Day is a miserable time of year. If you’ve spent February 14th alone, you already know what I’m talking about. If you have a long term partner, then you know it is nigh on impossible to avoid this supposed celebration of love turning out to be a huge anti-climax, unless you are willing to shell out a small fortune each year.
Perhaps the worst Valentine’s Day experiences are those that involve hastily-arranged dates and disastrous valentines gifts. And believe me, I should know.
My Valentine’s nightmare featured a rather over-eager young buck named Jan. I found him through a dating website and quite liked the sound of a “Norwegian gent with a passion for fine food and the great outdoors”. After all, I quite liked A-Ha back in the day and I hadn’t heard any horror stories about Norwegians. Not since Viking times, anyway.
Jan suggested a picnic in the local park for our Valentine’s date, which roused my suspicions that he was not only a bit forward, but also insane. A picnic? Outside? In February? But he assured me it would all be fine, promising to bring a warming flask of Irish coffee and some delicacies from his homeland, so, keen as I was to discover a cultured, well-travelled man, I agreed.
What I didn’t anticipate was that Jan would spend the entire morning before our afternoon rendez-vous in the florists.
When I arrived at our meeting place in the park, I couldn’t see Jan. Not that he had stood me up or kept me waiting. No, the reason I couldn’t see Jan was because he was hidden behind the largest bouquet of valentines day flowers that I have ever seen in my life. There must have been over two hundred flowers of all descriptions in this monstrosity. I almost expected local florists to appear on the horizon demanding he replenished some of their stocks, but I awkwardly accepted his gesture and we got on with the picnic.
But the valentines day gifts did not stop with the flowers. So keen was Jan to give me a good impression of his beloved homeland that the first item out of the enormous picnic hamper was a huge, stuffed, cuddly elk.
After almost taking my eye out with one of its antlers, Jan announced that he had brought with him a warming dish to kick off our picnic. He then proceeded to take out a camping stove and a saucepan, in which he warmed up our main course – elk stew!
The date seemed to last for days but, when it did finally come to an end, I bade Jan a hasty farewell and walked home as quickly as I could, depositing the valentines day flowers and bizarre cuddly toy in the waste disposal of a local factory. I tried to throw the memory of a disastrous Valentine’s Day in there with them, but it proved a little harder to shake off!
I think I mentioned once that I would settle for a Duke or an Earl in lieu of a Prince, but having met this Earl, perhaps I shouldn’t settle, and instead hold back for the real thing. Earl had reservations about meeting up, which he voiced in a long-winded message on my answering machine the night before we had plans. You see, he had only ever talked to my answering machine, and I to his. I’m a very busy person, and an unfortunate side effect of that is that you had better love me, love my answering machine. I always return phone calls, but not always at the best time. Earl thought this was weird, but I figured that there was nothing that we could talk about on the phone that we couldn’t talk about in person. His reservations, in fact, were making me wary. Jump in with both feet, and don’t be afraid to get wet.
Earl had picked a couple of possible locations, all in my general neighbourhood, that he was willing to make the lengthy commute in from the suburbs to come and meet me at. We decided on a neighbourhood jazz club to catch a band after some supper there. I had never been there, despite having walked past it for years, and my brother and his wife had happily dined there in the past, so I decided that this would make a fine date spot. So on a rainy weekday night I meet my earl in the foyer. He’s tall, gangly and geeky, normally attributes I find charming in a guy, but somehow, it’s just not working for him. He’s wearing a terrible shirt, a grey short sleeved button-down covered in a strange static linewave pattern that looked like he bought it in the Dixie Value Mall. Not that I judge guys based on their wardrobe, but there are some things that say volumes about a person, and his choice in clothes on a first date is one of them. If he cares about his appearance, it is important, but if he has no clue, it’s tragic. Anyways, we sit down, order some wine, and peruse the menu. It’s apparent that he has no clue about wither, but I think it’s charming that he is putting in the effort. He orders a run of the mill Seafood Linguine and a glass of Chardonnay.
And then the terrible happens. Bread arrives. He tears into it, butters it and takes a bite. And had butter all over his face and crumbs all over his shirt. He doesn’t really notice it, but then again, butter and crumbs are light, right? You might not notice them. But pasta sauce, linguine remnants, shrimp tail segments… the list continues. His entire meal at one point or another ended up somewhere on his face. This was rather unattractive. I found it impressive that he didn’t even notice, or alternately, didn’t seem to care.
About a half hour after dinner, and an hour into a thoroughly uninspired conversation that prove to me that not only did we have nothing in common, but that he really had no interests, no motivation and no sparkle, the band started. And what a so-called treat that was. A mediocre cover-band, we were treated with funkified renditions of George Michael’s Faith and several Stevie Wonder classics. He loved the band, and moved around the table to sit next to me, he said in order not to have to crane his neck to watch the show. Not that I thought they were worth watching. And not that there was any chemistry between us to justify this little move (the food and the shirt had taken care of that). If you have seen more than, say, 5 live bands, I don’t know how you could think that this was a good show. But alas, what do I know!
After one set of painful tunes, accompanied by absolutely zero conversation, I was tired enough to go home. We left the senior dating meat market (I swear, everyone looking to hook up in the Yonge and Eglinton neighbourhood over the age of 50 was there checking each other out) and went our separate ways. I tried to duck the hug, but was unsuccessful, so got instead the awkward rainy half-hug. I just didn’t want to press up against that shirt, for both the fashion, and the food.
You may be what you eat, but don’t wear it on your sleeve for the world to see.
It took a lot of analysis to figure out if my date with Todd was a bad date, or just an indifferent date. I mean, I considered going out with him a second time, not because I was wildly attracted to him, which I was not, but because there was nothing overtly wrong with him. We met up during the hockey playoffs, in one of my local neighbourhood haunts. He’s from Mississauga, which he had just recently moved to in order to be closer to his job as an Air Traffic Controller. How cool is that? I mean, I think dating an Air Traffic Controller would be wicked cool. Type A personality, for sure. Just my type, I think. We had nothing else in common, other than the fact that I thought his job was cool, and so did he. He was from a small town and was intrigued by my big city ways, artsy tendencies and devil-may care attitude. I like dating pilots (his former job) since there’s usually travel opportunities. Shhhh… that’s not shallow, it’s practical.
So needless to say, being unfamiliar to the big city, he was late. And in the intervening wait time, I had a sudden urge to flee. Being in one of my local pubs meant that there was a good chance that I would run into someone I knew, and I did. My entire family. Both my brothers and their wives (ok, one wife, one girlfriend). I begged then to keep their distance as this was a date, and already a socially awkward situation. I mean, can you image? “Nice to meet you Todd, this is my entire family who will be judging your every action.” They were well behaved, and only came to bug me as they were leaving, at which point they were introduced. What bugged me more is that Todd was annoyed that I didn’t introduce them earlier, nor have any inclination for us to join them. Sorry, but not my style—see comment above. Little things kept gnawing at me, but they were petty. He looked awful when he laughed, something that should happen to no one. Laughing traditionally makes everyone beautiful, or should, anyways. He had an awful earring, which he explained as his only shot at rebellion. Rebel on, white boy. But nothing was genuinely that bad. Neutral, but not bad.
Until the post date made the date bad.
He called me the next morning, explaining that if he was up after a late night out with me, I should be up too. Ok, if not a little too familiar for me. He asked if I wanted to go bowling with him and his sister, who was coming into town to visit. Now, just because you happen to meet my family in a bar does not mean that I want to meet yours the next day. He called again in the afternoon, and again in the evening. He called the following day, and the day after that. And then he lost his job and left sad messages on my machine like “You’re probably working right now, but of course, I’m not any more.” Yikes! One night out and I’m suddenly your only support system. Slow it down, farm boy. It took me over a week of not returning his messages to finally stop hearing from him. I like eager, but not desperate. One date does not a relationship make. He had shown no stalker tendencies while we were out, but making me wish my number was unlisted is just wrong. Next time, I’m looking for aloof. And an only child.
My oh my, what a hellish mistake this was. A text message in the middle of the date hell, pleading for some kind of family emergency. I suppose I shouldn’t be that hard on Tom, since, after all, it is mostly my fault that I found myself in this miserable predicament, but, let’s be honest—it’s never truly my fault.
I made the mistake of going out with Tom without ever having talked to him on the phone. I have done this before, but from hereon in, I will never do it again. We had several interesting conversations on Messenger, exchanging anecdotes and photos, lamenting the profusion of cars in the city and death of good cycling routes. He was an illustrator, who wanted to move into doing children’s books, but found that encyclopedias and illustrated bibles did a better job of paying his rent. He typed in complete sentences, and generally avoided common grammar errors, something I appreciated. Overall, entirely capable of carrying on a lucid conversation. We made plans for an impromptu meeting, as we were both at home without plans on a Thursday night, really, the new Friday. We met at a pub, about midway between our neighbourhoods. It was immediately when I walked in that I wanted to turn around and walk right back out, but he spotted me. There, bouncing back and forth at the bar, was my unwashed date. I mean, really greasy, and disheveled. Needed a hairbrush, cut and shave, and some clothes that hadn’t made their third time through a local vintage store. He laughed nervously and waved, and as soon as he spoke my first thought was “Oh my god, he’s retarded.” I know, I know… not nice. But I can’t help these things some times.
We sat down and I ordered a drink. He seemed to be half in the bag already, although it could have just been the way he was. He couldn’t focus on any one thing, nor complete a sentence. He was constantly at a loss for words, simple words that most people have ready access to he thought for belaboured minutes trying to construct. My guess is that he was autistic, and highly socially stunted. He kept making monkey faces, which he thought was funny, but I thought was creepy. He would blow out his lips and widen his eyes, and then laugh hysterically. He embraced his monkey nature, something I did not. To make matters worse, he was incredibly boring. He had never traveled, had no firm opinions about anything, and, since he couldn’t finish his sentences, decided that point form was often an acceptable was of order spoken thoughts. It was painful. His Rain Man-esque demeanour got worse as he drank, and I, thankfully, could manufacture an early class the following day to get out of it. I craved a conversation, not a long series of awkward giggles on his part while he patted down his hair. Evolution, indeed.
One of the shortest dates of my life—45 minutes. We met in one of those usually interminable lunch lines for Greek food in First Canadian Place. I had a slew of meetings that afternoon, and was visibly impatient. He was tall, well-suited and charming, and struck up a conversation about our current lunch line situation. I agreed to meet him for after work cocktails the following day. He suggested Canoe, and being one of my favorite places in the city, I quickly agreed.
Alas, from the moment I walked in to the fateful event 45 minutes later, I knew that this would be something of a bad date memory. I ordered myself a glass of red wine at the bar. He flagged the bartender, and said “Actually, get her a Sour Apple Martini.” He turns to me and tells me “This is my secretary’s favourite drink, you’ll like it.” But I don’t like Sour Apple Martinis, I do like red wine. I don’t like chauvinistic assholes who order my drinks for me, despite the fact that I had already done so.
So our conversation progresses from there. As it turns out he’s a broker. Quel shocque. I should have guessed from the perfectly tailored Zegna suits. Actually, let’s be honest. I like brokers, or any kind of type-A financial type. I like the high-strung, pushy bordering on obnoxious personality type that a broker make. I like the glam, the sense of entitlement and privilege, but sometimes it just goes a little too far, and John was one that really took it too far. Although the date was headed squarely downhill from the start, we gained momentum when we started talking about restaurants. One of my faves in the city is Crush. His wife’s as well, I find out, although it’s often too difficult for them to get a sitter and dine out as often as they would like. Wham! Square across the face with that one. There were no signs—no ring, no cell phone on the table, no previous comments. “Oh, you have a wife,” I say. He then describes her to me—the typical power wife with the perfect power kids. Kind of like Annette Benning’s character in American Beauty. And he loves her, in his strange way, he admits. I become silent, trying desperately to figure out how my presence in this situation fits in. I have been involved with married men before, but this seems different. He doesn’t seem to be your typical wandering eye.
Turns out John has a proposition for me. He’s not looking for any baggage, not looking for any involvement or commitment. He’s looking for a little lunchtime something something. A liquid lunch, and a quick spin in a nearby room. I’m cute, I’m sexy, I’m outgoing, he says, so what do I think? I’m floored is what I am. Although hindsight being 20-20 and the proposition now may not be so absurd, in the heat of the moment I was livid. I had my first (and so far only) drink slinging episode. The last of my hated sour apple martini in the middle of his chest. Without witty point, I left immediately in silence. I had always thought I would say something really cutting, but I was just offended.
In retrospect, I wish I had said something. Heck, maybe it wasn’t such a bad proposition, but then again, I only have an hour for lunch. The less I can do to promote premature ejaculation, the better.

Leave A Comment