Love among the laptops: Navigating the waters of dating in the online age

Love among the laptops
Illustration by Kathryn MacNaughton

I will start with an admission: I am a terrific failure at online dating. It’s not that I’m a Luddite when it comes to cyber-communication; I grew up on the cusp of the generation that came of (dating) age during the digital era. Yet somehow, meeting someone online reduces me to the level of awkward small talk at a wedding with an elderly uncle: “Where do you live?” “Is it nice there?” (Uncomfortable pause.) “What do you like to eat?” And the perils of online communication don’t disappear after the first few dates: A guy I was seeing ignored my Facebook friend request until I retracted it, embarrassed; an ex-boyfriend abruptly untagged himself from every photo we appeared in together. The internet, for all its Google Pluses, has created plenty of minuses in my love life.

I started online dating after seeing my friends take to it with an ease that made it seem like the Net-A-Porter of courtship: See something you like, order it and try it on at home. I’d see them accepting Facebook invitations to his friends’ Super Bowl parties and Instagramming Sunday bike rides on Twitter. Social media has made it easy to present a seemingly impossible relationship ideal, complete with wholesome dates straight out of a J.Crew catalogue. (You went apple picking together? Are you serious?)

At the one-year online-dating mark, I wonder why I don’t have my own bag full of apples. I’ve been using OkCupid, which has some 100,000 active members across Canada. The fact that it’s free makes it feel like any other form of social networking, and the men on there are just like the ones I see during the lunch hour downtown: some suits, some creative types and plenty of tech guys. Most women I’ve spoken to either pay a subscription fee to meet guys on Match.com, frequent free sites like OkCupid or Vancouver-based Plenty of Fish (PoF), or use specialized services such as JDate, for meeting Jewish singles, or tastebuds.fm, where matches are made based on shared music preferences.

At first, I felt like I was sending out endless cover letters for a job, but without knowing the requirements. The last dating Valhalla to which I aspired to gain entry was governed by the cosmos and Manolos of Sex and the City. In dating terms, that world is now hopelessly outdated—the only thing a computer was used for back then was housing Carrie’s puns. As if they had an oracle on speed-dial, those four single women would sometimes quote The Rules when making dating decisions, and these have evolved with the times—at least in terms of technology.

“With facebook, twitter and blackberry messenger (I know you read my message; why aren’t you replying?), how is it possible to be mysterious, to disappear between dates?”

I purchase and consult the original book’s follow-up, The Rules for Online Dating. Written 10 years ago, it’s a little out of date, but swap AOL for PoF and essentially the mechanics are the same. A mix of common sense and what bitter guys call “playing games,” The Rules range from playing hard to get (don’t answer emails for 24 hours, disappear between dates, keep conversations breezy, appear busy) to personality reforming (don’t interrogate him about his online profile, don’t be his therapist, date many men at once until one asks you to be exclusive). Some of them feel practical, some hard to manage, others downright old-fashioned. With Facebook, Twitter and BlackBerry Messenger (I know you read my message; why aren’t you replying?), how is it possible to be mysterious, to disappear between dates? And if my social engagements happen offline, should I fabricate a hectic schedule of Facebook “events” in order to appear busy enough?

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