The Worst Date Ever story came about as a bribe to my readers. In exchange for a Bloggie
nomination, I promised to tell the story. While a number of people
submitted my name for nomination, I didn’t make the final cut, but
decided to tell the story anyway.
People have asked me, via
comments, email, instant messaging and face-to-face conversation, if I
ever have good dates. I do, and when they go well, they go stunningly
well. I had a particularly memorable and bloggable one last year, an
unexpectedly wonderful one in the spring of 2000 in New York City, one
dreamlike on in Prague just after New Year’s 2000 and one unforgettable
one on my birthday in 1992. However, the one which makes the best story
is the earliest one: one particularly sweltering night in Montreal in
August 1987, when what should’ve been a disaster turned into something
(Besides, I think that sixteen years is well past any statute of limitations.)
could simply dive right and and just tell the story of the date, but it
would simply be nothing more than a cute little tale of little more
consequence than a sitcom episode. Big Life Moments like the Worst Date Ever
don’t happen in isolation, but in the context of the life surrounding
them. Just as every particle in existence exerts a pull on every other
particle to give the universe its shape; every experience we have
exerts its own gravity on every other experience, giving shape to our
So as promised, here it is: the serialized story of
the Best Date Ever, by way of the scenic route. This is going to take a
helluva of a lot of installments, but I think you’ll find the journey
an interesting one.
This story is dedicated to anyone who feels alone, unwanted or is suffering atrophy of the heart.
Quid Pro Quo
Toronto, May 1986
If airports smell like impatience (as I believe Douglas Adams wrote), high school principal’s offices smell like remorse.
In my eight years at De La Salle College “Oaklands”,
a picturesque Catholic school set on a prized hilltop plot of land
donated to the Christian Brothers by an eccentric millionaire’s widow,
I had never been called to the principal’s office for reasons that
would end up on my permanent record. Although some of the school’s more
notorious troublemakers were my friends, I was generally regarded as
one of the good kids, even if I always didn’t “apply myself” to my
It was a particularly bright and sunny morning in
late May, and the gorgeous weather outside made the fact that I was in
this office for disciplinary reasons more painful. I decided not to
stare outside the window, but instead at a rather generic scenic
painting of a forest that hung on the institution-pale-green walls of
My Inquisitor, Mr. Davies, the school principal,
kept me waiting for fifteen interminable minutes, while chatting with
Ms. DeCesare, the bursar’s secretary. While I couldn’t hear what they
were saying through the closed glass door, I could tell by the sound of
their voices and their body language and furtive glances and gestures
in my direction that they weren’t doing official business, but making
small talk, possibly about me.
It was a tactic meant to wear me down and make me willing to name names.
Thirty-two hours earlier
must’ve been the most suspicious looking lot on that warm spring night:
ten boys, all at the end of their teenage years, clad head-to-toe in
black (some even in balaclavas), piled into a van that was slowly
making its away across a darkened parking lot with its headlights off.
eased the van to a quiet halt at the edge of the parking lot that was
both farthest away from any lights and closest to the school building.
“Awright,” he said, turning the engine off and turning to face the rest of us in the back. “Let’s do it.”
One of us slid the side door of the van open. A slightly drunk Pazzo let out a war whoop.
“OPERATION ANNIHILATION!” he yelled.
I quickly silenced him by covering his mouth with my hand.
“This…is…a…stealth…mission!” I hissed. I removed my hand from his mouth, wiping off the whiskey-scented drool on the leg of my black jeans.
“Oh yeah,” was his sheepish reply.
“C’mon,” said Ray, who was supressing his laughter. “Let’s make this quick.”
Pazzo, Ray and a few others a long with me were on Beta Team. Beta
Team’s mission was to take several dozen rolls of toilet paper and turn
the trees of St. Michael’s College, our rival school, into weeping
willows of bum-wad. The other members of The Operation, Alpha Team,
were charged with the duty of rendering the school’s locks inoperable
by rubbing chicken boullion into the keyholes.
Beta Team made short work of the trees, and four dozen rolls of bathroom tissue later, we returned to the van.
“I fucking hate St. Mike’s,” said Pazzo, “bunch of stuck-up assholes.”
Pazzo’s rage was misdirected. He actually hated only one
St. Mike’s guy, whom some girl from our sister school, St. Joseph’s had
chosen over him. St. Mike’s was guilty by proxy, which probably made
sense according to the pretzel logic of the kind of guy who would curse
all the sailors of the world after getting food poisoning from eating a
“I got an idea,” he said, grabbing a can of spray paint and running out the door.
“I hate it when he gets ideas,” said Ray.
you double blue,” said Mr. Davies, when he finally entered his office
bearing a single file folder. The swear words sounded doubly obscene
coming from him.
He walked to his desk, tossed the folder
onto it, took off his blazer and placed it on his chair. He looked away
from me and out his window.
“Four hundred dollars,” he said,
watching a group of “Greenies” — the younger students, who wore green
blazers, while we older ones wore blue — playing frisbee. “Do you know
how much that costs, on a per-word basis, Jose?”
Mr. Davies always preferred to address me as “Jose” rather than “Joey”.
hundred dollars a word, sir,” I answered nervously. The fact that I
knew he was toying with me didn’t make me feel any better.
hundred. Dollars. A. Word,” he said, elucidating each word very
carefully. I was reminded of a trick that some of the chess players who
played on the public tables off Yonge Street intimidated their
less-experienced opponents: they’d slowly twist each piece they moved,
as if screwing bolts into place.
“The actions of your friends
on Monday night have tarnished this school’s fine reputation forever.
Do you know what a man has if he doesn’t have his reputation, Jose?”
“He has nothing, sir,” I said, wishing that he would skip this
tea-ceremony-cum-torture-session and just tell me what he wanted.
Has. Nothing,” he said. He was facing away from me on the words “he”
and “has”, but turned on his heel and faced me from across his desk,
his arms in an inverted V-shape and his legs together, glaring at me
like an angry tripod. “Nothing!”
He’s quick for an old man, I thought. Had I not been so nervous, I’d have laughed at the Shatnerian ridiculousness of the gesture.
stood upright and faced the window again. “You, however, have a
reputation. It’s good, and if you apply yourself, it could be great.”
“Thank you, sir.”
“I’ve known you for eight years — eight years! — and you’ve been a good man all the way through. Although you are friends with some of the ne’er-do-wells…”
tapped a cassette tape that was rested on a two file folders that I
hadn’t noticed on his desk. They were the permanent records of Nik
Roland and Will Stepney. During the previous week, they’d managed to
sneak into the control room for the school’s public address system and
replaced the cassette of the national anthem with one that had a
synthpop tune where the vocalist was yelling “Suck me off! Suck me off!
Suck me off!”
“…and you fancy yourself as some kind of
clever prankster, you are too much of a gentleman, if I may be so bold,
to stoop to petty vandalism.”
“Thank you, sir.”
“Don’t thank me just yet.”
Finally, I thought, here it comes. I could feel my pulse in the veins around my throat, and I could swear that someone was slowly draining the air from the room.
He slid Roland’s and Stepney’s records aside and took a seat. He opened the folder, which I realized was my permanent record.
excellent. Computers: well, I know you’re our resident computer whiz
kid. English: Mr. Cheley says you could be our next Oscar Wilde.”
for the writing and not the…the thing for boys, sir,” I said, in a
pretty foolish attempt to inject a little levity into the situation. I
was on an express train to Hell, so why not have a little fun?
One eye glowered at me from behind a bifocal lens.
“Too bad about these chemistry and math marks. They’re okay, but probably a little low for applying to engineering. That is what you want to get into, isn’t it?”
“I expect that you’ll probably repeat these courses.”
“Yes, sir. I’m going to do chemistry in summer school, and redo the three maths in the fall.”
“I thought that if I had to repeat courses, my parents shouldn’t have to pay for it, sir.”
“Public school, eh?”
“I found a good one. They even have a robotics course that I was going to try in the winter term, sir.”
“So…” he said, his voice becoming more conspiratorial. “You only need to repeat these four courses, is that correct?”
“You sure you don’t want to, oh, I don’t know — repeat them all?”
“But I already have good marks for those courses. They’re right there,” I said, gesturing towards my record.
“You have them…insofar that I’m allowing you to have them.”
The words, although spoken in a soft conversational tone, hit me with gale force.
“Jose, do you know the meaning of the Latin quid pro quo?”
“It means…” I said, my voice diminished by the sudden dryness in my throat. “..tit for tat.”
“Correct,” he said, “if colloquial. Tit. For. Tat.
This is an exchange that I am willing to offer you. I will make sure
that your good marks get transferred to whatever school you will be
attending this fall. That way, you will not have to repeat those
courses. In exchange, I want names.”
“Names, sir?” I asked, pointlessly. I knew what he wanted and he knew that I knew.
know you were there. I know you know who did it. I know that you and
some others were responsible for the non-destructive parts of your
little graduating student prank. That’s tradition, and I care a whit
about that. But some of your number are responsible for spray-painting
‘FUCK YOU DOUBLE BLUE’ across the entire front wall of another school!
I WANT THEIR NAMES!”
“Sir…” I said, weakly. I struggled to think of something to say, but I didn’t have a bargaining chip. They were all his.
“I know. You are worried about your
reputation now. I hear that irony is a major literary device that is
covered in the English class in which you did particularly well.”
I prayed for a stray meteor to hit the school and crush the office, but the prayer went unanswered.
you are generally un upstanding gentleman, I am willing to make this
easier on you. You will not be required to provide me with names.”
want you to use your powers of persuasion to convince any one of the
people who spray painted St. Mike’s to step forward. He will provide me
with the names. That way, you will not be directly responsible for — I
believe the vernacular term is ‘ratting out’ — the gentlemen in
question. In exchange, I will transfer your marks to your new school.
If this man that you provide to me provides me with names, I will
reinstate the prom.”
The day earlier, he’d announced that the prom was cancelled until those responsible revealed themselves.
“If you cannot produce this one man in forty-eight hours, I will not
transfer your marks, and no record of the courses in which you excelled
will exist. You will have to repeat everything, not just a few
That wily old motherfucker, I thought. I’d just had my first bait-and-switch pulled on me.
hours. One man,” he said, as he showed me out of his office. “It
shouldn’t be difficult for a intelligent and resourceful gentleman like
The door to his office shut with a sound that
reverberated down the long empty hall. I glanced up at the clock on the
wall. 9:15. I was late for my exam.