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

Love among the laptops
Illustration by Kathryn MacNaughton
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, frequent free sites like OkCupid or Vancouver-based Plenty of Fish (PoF), or use specialized services such as JDate, for meeting Jewish singles, or, 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 In dating terms, that world is now hopelessly outdated—the only thing a computer was used for back then was housing Carrie’s puns.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?

Love among the laptops
Illustration by Kathryn MacNaughton

Sherrie Schneider, who co-wrote The Rules with Ellen Fein, has heard all of these concerns from clients, which is why the pair is working on a new book that encompasses social media and texting. Schneider is exacting about the level of commitment—and adherence to traditional gender roles—required for The Rules to work. “Women tend to post every thought they have, and their thoughts are very transparent,” she tells me. “You should not use Facebook that way if you’re dating. You should be more mysterious. A guy shouldn’t know where you are every minute.” I can certainly practise moderation, but how do we even get to the part where we become Facebook friends? “He should friend you,” declares Schneider. “A woman friending a guy is not The Rules, because that’s pursuing.”

OK, but I really want to look at all his photos and see how pretty his ex-girlfriend is. Doesn’t everyone? Julie Spira, the L.A.–based author of The Perils of Cyber-Dating: Confessions of a Hopeless Romantic Looking for Love Online, says the urge to research a prospective date is natural. “Do a Google search, make sure they work where they say they work and that there’s nothing bad about them,” she begins. This is sensible advice my mother would appreciate. “We also want to make sure their Facebook photos match their online dating photos, and find out if we have any friends in common. The next thing would be, well, let’s friend each other. Well, no, don’t friend each other.” Her reasoning: Just as you will be mining his profile for useful or petty information, he will undoubtedly be mining yours. (Perhaps I should delete all those photos of corgis in costumes that my friends keep posting on my wall.) “You still want someone to get to know you,” says Spira. “If everything they get to know about you is because they saw it on Facebook, what’s left to talk about?”

The Rules dictates that if a guy hasn’t asked you out after four emails, it’s time to move on. The Toronto writer who goes by the nom de guerre Sexy Typewriter has gained a loyal following with her “dating failure blog,” and she agrees it’s best to keep things moving along. “I had a heart-pounding crush on this one guy—on his words and his photos—and then I met him and he wasn’t that guy. I was sad that that first guy didn’t exist because I kind of loved him,” she says. “This is why I would say only exchange a very small handful of messages with someone before you meet up, otherwise your expectations grow to a point where no one can fulfill them.”

For Keighty Gallagher and her friends, OkCupid is as much a part of the social-media mix as Twitter and Facebook. “If a guy asks me out within the first two to three messages, I get turned off,” says the pretty blonde marketing assistant, who’s in her early 20s and lives in Vancouver. “I like to take my time with these things, so if a steady back-and-forth conversation lasts even a few weeks and he hasn’t asked me out, that’s ok with me.”

“Unfriend somebody if you think it’s going to upset the new person you’re dating. Those lovey-dovey shots, just take them off, or at the very least untag yourself and him.”

Perhaps it’s an age thing. Lisa Bernardin, a Vancouver human resources adviser in her early 40s, signed up for Plenty of Fish a few years ago and went on 11 different dates. “Guys between 38 and 43, they’re not into playing games and wasting time,” she says. “They want to meet and figure out if there’s something there.”

Eventually, Bernardin met someone irl (in real life), but says she’d go online again if she found herself single in the future. “It helped me to find out what I’m looking for,” she says. “It got me out there and helped me conquer my fears about approaching guys. You ask if they want to get a coffee, they say no, and it’s no big deal.”

As for that ex who untagged himself from my photos, Spira says this is perfectly acceptable behaviour when a relationship has run its course. “Unfriend somebody if you think it’s going to upset the new person you’re dating,” she advises. “Those lovey-dovey shots, just take them off, or at the very least untag yourself and him.” However, she advises giving a heads-up and an explanation before you go about this exorcism—the modern version of separating out your possessions.

Currently apathetic about my relationship status, or perhaps feigning ambivalence as a means of self-preservation, I’m still logging on and looking, because sitting on my couch with my laptop is a lot better than the bar-stool alternative. I still don’t know if I’ll ever be able to match the dating successes of my friends, but whether it’s online or irl, I know that I’m not going to find a good apple unless I get out there and start picking. 

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