The secret to online dating: Just don’t be yourself

Manisha Krishnan on the dates behind the story

Photo illustration by Sarah Mackinnon

Recently, I wrote a story about the wealth of expert advice available to help singles up their online dating game.

There are professionals who will scrutinize your photos and select the best ones (bathroom selfies need not apply), write your profile and even message prospects on your behalf. If it sounds bizarre, it is. I can vouch, because I tested it out.

Save for a very brief stint, I had never online dated prior to this experiment, so I was curious and clueless — a perfect candidate.

The company I hired, A Million Matches, claims to be Canada’s first online dating assistance company. Their prices range from $99 for a basic profile to a staggering $1249/month for the “executive package,” which includes pre- and post-date feedback and criminal record checks. (If you’ve got $1,200 to spare a month there are probably better ways to land a date.)

Anyway, soon after contacting owner Amelia Phillips and telling her that Maclean’s was interested in writing about her business, I came across my first red flag, when she advised women to avoid being “braggy.” Tone it down when talking about career-related achievements, places travelled to, and so on, she said.

“If a guy thinks there’s no way he’s going to measure up, he might not message you.”

A little too Mad Men for my liking, but Phillips, a former corporate lawyer, was insistent.

My other hesitation was authenticity. Using this service means trusting a complete stranger to present you in what they see as the best possible light — which may or may not be accurate. Beyond that, A Million Matches actually messages singles on behalf of their clients in an attempt to break the ice.

“For our male clients, we do find ourselves complimenting women and crafting a message that will get a response from a woman that we know is getting a dozen messages a day,” said Phillips. Ladies, imagine being wooed by one of your suitors, only to later find out it was actually his female dating assistant doing the talking. Somehow it’s less charming.

So, how did I fare?

Well, less than two weeks after joining, my assistants had already emailed 115 men in the Greater Toronto Area, and “winked” at another 35.

My profile was full of disarming lines like “Send me a funny message and I may be yours, lol” and “Arrested Development has got to be the bestest TV show ever.” Bestest. It’s not even a word. But more troubling than what was in the profile was what it was lacking: personality and wit. Being upbeat but generic, if I understood correctly, was the golden rule of online attraction.

The messages “I” was sending out ranged from fine (“What kind of music do you like?”) to downright atrocious (“How much money do you make? Lol, kidding”).

And I couldn’t always keep track of whom the company had emailed for me, so I ended up contacting the same person twice in some cases — stalker much? Occasionally, a guy would send me an out-of-context note that made no sense. A great example: “Hey, I’m not sure when you messaged me. I had no idea my niece vomited. Makes it seem more natural.” I was as confused as you are.

In a month, I went on a handful of dates. Some were pretty bad (awkward racial jokes), most were unremarkable. Probably anyone who has tried online dating can relate.

But I noticed that the profiles I found most appealing were anything but generic. They were a little bit sarcastic and pithy; frankly, I didn’t feel my own profile measured up.

On the flip side, A Million Matches definitely plays the numbers game, sending out messages to far more people than most of their clients would probably ever contact themselves. And that can work out — it did for Yolande, the executive I interviewed.

But I’d have to disagree with the experts on their approach.

It seems to me, the point of putting yourself out there online is to skip the BS, and present your truest self. If you have bad grammar, the person you’re dating should know that. If you think shirtless selfies are cool, ditto.

In the end, I’d rather keep it real and attract fewer, but more compatible guys. The alternative, being overlooked by a good match because of a misguided attempt to fit the mold — that would be the worstest.