How To Go From “It’s A Match!” To “Pick You Up At Eight”

We live in a world where online dating is the norm and meeting Mister or Miss Right rarely happens organically anymore.

One of the common questions asked by single people in the city is “How do I do ‘online dating’?”

I complied some easy and quick suggestions to make online dating a little less overwhelming:

  • Response messages should be short and sweet.  Little tidbits that will give someone an insight into you.  This means hobbies and interests.  Keep long winded stories to your face-to-face dates.  Reading a whole novel about how great you are is draining and boring.  Plus, what is left to talk about in between the awkward silences on your date?

  • Limit the 50 questions.  In fact, stick to one or two questions per message. Too many questions can feel overwhelming and they can quickly lose interest and not respond.  Keep the questions to a minimum and make sure you ask questions that require more than a “yes or no” answer.

  • Don’t make it dirty.  Keep the dirty talk and nude pictures out.  THIS IS NEVER OK.  In fact, if this is the way you’re starting off, it’s clear the intentions are not long-term nor serious. Be prepared to be blocked and deleted.

  • Don’t be negative. Don’t waste your time telling him/her over email how horrible online dating is and that you haven’t met anyone great.  No one wants to hear you whine and complain about online dating – we’ve all heard it.  Try to stay positive in your dialogue and hopeful.

  • Don’t drag online correspondence for too long.  If you’re having  good banter back and forth, send them your phone number and suggest moving the conversation to a call or text – or if you’re bold enough, suggest a date plan.  Warning: if you drag on the text conversation too long, it will die down and they will lose interest.

  • Read their profile.  The worst is answering questions that have been answered already on their profile summary.  Show your interest goes beyond the picture.  This also means phone apps.  Make sure to check if they have inputted a bio.

  • Don’t just say “Hi”.  Put some effort in your initial message.  Comment something you noticed in a picture or in their profile.  Keep it light and fun.  Save the serious convos for in person.

Online dating can seem redundant, but try to stay optimistic and hopeful.  There is someone out there for everyone.  It just might take a while to find them – a few swipes away.




Clarinda Brandão

Clarinda Brandão

Clarinda Brandão, Registered Psychotherapist & Relationship Expert at Psychotherapy in the City in Toronto. Individual and Couples therapy.