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Relationship Advice: Dating Again

How do I survive the frustration of online dating…
By Adam Segal
It’s been two years since my break-up and I’ve finally decided to take a stab at online dating—for better or for worse. I’ve had single friends share battle stories of navigating dating in this electronic age but always thought they were just complaining or focusing on the wrong people. Now I can confidently say that I am just as frustrated as all of them—I have had a zillion first dates with guys I’ve met online that just don’t go anywhere. Several of them are guys who seemed really interesting when we were swapping messages, but in person it immediately falls flat. When it doesn’t work out, I head straight back to the gruelling hunt. I don’t know how to keep my romance-seeking energy up after so much disappointment or how to be more skilful at weeding out guys before I invest too much energy. I feel like one more crappy date could push me over the edge. Besides becoming a celibate monk, what are my options? –Frank
Dear Frank:
Online dating is no easy pursuit, and on some level it’s most important to simply acknowledge this truth—it often feels like heavy lifting and is tinged with frequent false starts and letdowns. There’s comfort, though, in knowing that this experience actually connects you to so many others who are trying to stay hopeful despite frequent disappointment and truly horrid first dates.
There was a time, before smartphones and endless profile scrolls, when people could meet face-to-face and pretty quickly assess whether there was any physical or personality chemistry. With online dating, so many folks can competently create snazzy self-descriptions and send witty messages. All of this posturing can encourage a dreamy hopefulness that things will simply blossom in-person—which, as you’ve already discovered, is a fantasy.
Here is a general guideline that could save you lots of time and spare you unnecessary fantasizing about men you don’t really know: if you have genuine interest in someone based solely on their profile and initial messages, take things to ‘in-person’ as soon as possible. There’s really no better way to cut through the haze induced by cheeky pick-up lines and heavily filtered photos—a truly virtual reality—than a straight-ahead meet-up. Your initial meetings with these guys are really just that: a moment to actually check out the chemistry, which will guide whether a true first date should happen at all. Seeing it this way will help reduce the pressure and help you maintain a more realistic stance toward the whole transaction.
As for the burnout you’ve been feeling, there’s no quick fix. It’s going to be essential that you don’t make dating (or even scrolling on apps) your full-time vocation—this will only foster resentment and despair on those occasions where it all falls flat. Continually check in with yourself before you head online: are you choosing to fire up the app because you actually have the energy and desire to attempt to connect with some new guys? Are you bored and trying to boost your mood by getting some quick validation? If you find yourself frequently in a zombie-like trance and reaching for your smartphone as an electronic pacifier, do the opposite—reconnect with the real world around you.

ADAM SEGAL, writer and therapist, works in private practice in downtown Toronto. Ask him your relationship or mental-health questions at

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