the date from hell

(from the Leah Files)

Later this week I’ll be posting the video (plus audio!) of my recent interview with the radiant British writer Caro Giles, author of the memoir Twelve Moons. It’ll be sent out to paid subscribers only, so if you’re tempted to upgrade, now might be a good time.

Over the course of our chat, Caro and I tackle the subject of dating — specifically how awkward and disorienting it is to encounter strange humans in a romantic context when you’ve recently published a memoir. Is it possible to be mysterious and alluring when a highly curated version of your life story is available for download on Kindle? (Answer: No. But we have other charms, like being radically honest and lacking normal boundaries.)

Today in advance of our interview, I am also reposting a old column of mine first printed in The Globe and Mail’s Style section way back in January 2002, when I was a just a fresh-faced baby-writer.

Although there was barely an internet in those days The Date From Hell column went analogue viral (particularly in Toronto’s finance district— when you read it you’ll see why) and later once there was an internet, it went viral-viral. Amazingly I still get emails about it to this day. Some columns follow you around your whole life and this is one of mine. There are others, of course, in particular the one about vajazzling which I will not be reprinting it here or anywhere else, just in case you were under the impression I don’t have editorial standards. Ahem.

As an advance update, the suitor in the Date From Hell later married and had children with a friend of a friend of mine and suffice to say he is not in Palm Beach with his wife as they divorced soon afterward (not that I judge him on that front, obviously… the poor guy). Anyway re-reading the piece made me laugh — not only because of the excruciatingly-date 2002-dot-com-bubble-bling trappings of the date itself (which would be unthinkable today) but because it reminded me that even back when I was unencumbered in my twenties and being chatted up by society bankers at black tie charity events, dating was still every bit as excruciating, ludicrous and utterly comical as it is today.

I’ve softened so much in the years since I wrote this. True I still have an edge, I just don’t feel the same need to sharpen it against every available surface. Plus I’ve earned it! I appear to take myself quite seriously in the column but in reality it was a pose — I had no sense of who I was or what I wanted or valued, which is of course how I ended up on the Hell Date in the first place! I’m a lot more forgiving these days, not just of other people (including all the poor unsuspecting men who had the misfortune of buying me a drink), but also myself.

Anyway, here’s a picture of me being a decadent, haughty, self-serious pre-internet 20-something, rocking my pearl earrings and designer bustier back when Paris Hilton was still setting hair trends.

(It wasn’t easy growing up the genetically-engineered lesbian love child of Rene Zellweger and Baby Spice but somehow I pulled through.)

Buckle Up for the Date from Hell

Baby Leah McLaren

People are different. Very different. One woman's waking nightmare is another's rose-petal-strewn hot tub overlooking Niagara Falls. While this might sound obvious, take it from me, it's all too easy to forget on a bad date. By "bad," I don't mean an organized encounter of the slightly awkward, boring or not-quite-chemically-clicking variety. I am talking about a truly torturous date. The sort of that starts off weird and gets increasingly surreal, and not in a quirky Hal Hartley movie kind of way either.

At a downtown outreach centre in the city where I live, a group of smart prostitutes circulate and update a list warning fellow hookers of clients to avoid at all costs. It is called the Bad Date sheet.

I have often wanted to start a similar reference sheet in the straight world, but have long realized it would never work. For one thing, the date crimes committed in my cohort are almost invariably social rather than psychopathic and sadistic (despite all those ardent warnings from the Women's Centre Safe Space committee in university, I haven't yet encountered the legions of rapists and girl-hating pugilists apparently lurking in my midst on the dating scene). For another, everybody is different. One woman's waking nightmare is another's . . . you see where I'm going with this.

Which is why, when the young finance executive arrives to pick me up half an hour late with no apology, skippering a chauffeur-driven limo the size of my apartment and yipping into a cellphone, I know with sinking certainty that my own personal, tailor-made Date From Hell is about to begin. Beware the man who does not apologize,I think as the driver helps me up the stairs into my steel chariot, for he knows not what he does wrong.

There are two mini-bottles of Perrier chilling in the drink holders in the back where we sit, like two little kids buckled into car seats. The Date From Hell opens his and chugs it, then looks amply disappointed when I fail to do the same. En route to the event we are to attend, I feel a mounting pressure to drink the complimentary beverage. When it becomes unbearable, I twist off the metal top and take a sip despite my lack of thirst. It tastes off somehow, which is impossible but makes perfect sense.

The party goes swimmingly. We talk to different people at opposite sides of the room. Afterward, I find out he has made a reservation for dinner. Re-ensconced in the limo, he turns to me and asks if I would mind if he makes a call, since, "in my business," the Date From Hell explains, "you're on call 24 hours a day."

He informs the driver of the restaurant's general location (I've never heard of it) and then proceeds to rant into his handheld as we drive up and down the street looking for the venue. He sounds roughly like this: "Hey. I'm just sitting in the back of a car with a gorgeous girl, and yourself? Listen, my friend, we have to get on that pronto. Yup, that's what I'm saying. Sorry but that crap doesn't fly with . . . No, no . . . Listen, you tell [insert name of famous tycoon here] you tell that fucker that he'd better get on board or he's not going to see dick for the [insert name of famous tycoon's pet cultural institution here] That's what I'm saying. I've got a conference call with [insert name of another well-known industry baron here]tomorrow morning, and he's on board. That's right. No, listen friend, you tell that little prick if he doesn't . . ." and on and on for 10 or 15 minutes in that vein, leaving me to wonder if there is anyone at the other end of the line.

When the driver interrupts to ask for more specific directions to the restaurant, the Date From Hell snaps, "Can't you see I'm busy? Just find it."

Somehow we get there. The venue is a sterile place on the ground floor of a condo building in the business district. My companion, now detached from his phone, is friends with the owner. When the waiter arrives, he tosses the wine list aside. "I'm not much of a wine guy," he says, ordering vodka, which he drinks through dinner. "You do smoke, don't you?"

After orders have been placed, the Date From Hell turns to me and smiles. "I don't read The Globe and Mail because I find it to be too much of a left-wing paper, but I had my secretary pull up a couple of your columns in research for this date," he says, as though I were a family of Afghan refugees he was offering to put through college. "So tell me about yourself, Leah. I presume you don't want to write a social column for the rest of your life."

I cough, blink. Remain glued to my seat. Cannot move for fascination. Could it possibly get worse?

I turn the conversation away from me. Someone close to his family recently left business to return to politics. A tough decision, I remark. He agrees.

"It's all about money and power," he explains. "Me? I'm a money whore. What it really gets down to is, where do you want to be when you're 50? Not at some rubber chicken charity dinner in some small town up north, I'll tell you that much. When I'm 50, I'll be sitting by the pool in Palm Beach with my wife and kids."

The waiter comes around and I decline dessert. "Good," says the Date From Hell. "I hate fat people. Don't you hate fat people?"

In a recent article for The National Post, freelancer Andy Lamey hilariously laments the dating pitfalls of right-wing politics. "A certain type of woman," he and his free-marketer friends lament, "would never date a neo-con." After my Date From Hell, I am beginning to understand why.