Home » A Single Girl’s Dating Survival Guide: 6 Commandments

A Single Girl’s Dating Survival Guide: 6 Commandments

This week has been a blur of writing for clients and working on my first video for you guys. Yes, I said VIDEO! I am happy to report that I taught myself how to use iMovie and I am no longer horrified by the sight of myself on camera. Make sure to check back on Monday to catch me in motion! Putting together a short video is fun but time consuming. Luckily my friend Vanessa from Dare My Truth kindly stepped up & wrote a guest post for me. I’ve already waxed poetic about my bizarre experiences as a 20-something dating in Toronto. I thought it would be cool to share someone else’s take on it – someone who is a few years younger & is still fighting it out in the trenches. Take it away Vanessa!

Source: weheartit.com via Simone on Pinterest


Being 20something and single in Toronto for the past 2.5 years has been akin to thwarting wild animals in the Amazon (with heels on, though I’d prefer flats).

To be honest, I was gunning for a real relationship, in part so I could feel comfortable getting down and dirty again. Once I let go of all needs and expectations, I acted differently and dating potentials fell from the sky. Here are some common mistakes and how I fixed them:

  1. Don’t define a “successful/fun” night out as one where you get asked for your phone number

Let’s face it, clubs are a superficial world where talking is discouraged. Even though I told myself I was going for the music, dancing and my friends, I’d still feel disappointed (read: unattractive) if I didn’t get approached by someone.

Instead of relying on external validation from nobodies, take it as a compliment since guys at clubs are after an “open bar” policy where beauty and wit are not required.

PS. If you make out with Mr. Club he won’t really take you seriously in the day light. However, if it’s a quick make-out you’re after, confine it to the club and go nuts!

  1. When you meet a dude that seems like Mr. Right, don’t feel like you have something to prove

In the past I’d meet someone who was either doing fantastic things with his life (an entrepreneur for example) or Hollywood level good looking (Chris Pine, anyone?) and become unnerved. I secretly believed I might not be good enough for them and would take on the mentality of an insecure interviewee.

Ladies, this is crazy. You have just as much to offer, if not more, and you are only seeing a very superficial, rudimentary version of him. Remember that like a job interview, it’s just as much about you assessing their “fit” as it is for the other side of the table.  In this economy, NOT CARING what he thinks is a skill in limited supply and will likely to get you hired for a second date.

  1. Lessons in Phone Etiquette.

First off all, pay attention to whether Mr. New Guy chooses to send you a text message or pick up the phone old school styles. The latter is a sign of real interest and sets the stage.

Secondly, I think one meaty conversation before a first date is enough to gage personality chemistry. If it exists, try to wait until your first date to continue the stimulating word exchange so you can assess visual communication cues as well.

PS  If you’ve been dating 3+ weeks and the phone calls are still few and far between he is generally not “playing it cool” or  “super busy”. He’s just not that into you. Trust your gut.

  1. Don’t spend excessive effort getting ready for your date

The day I went out and bought the best push up bra I could find was the day I was stood up for the first (and only) time. Besides, that bra is going to come off sooner or later…

Excess primping can build anticipation, expectation and anxiety, which you don’t need. A good first date is all about being comfortable in your skin and feeling like yourself.  Besides, didn’t Drake teach you that guys like more of a natural look? You have more to offer than your looks so keep it simple and stress free.

  1. Don’t get too creative with your first date itinerary

Let’s face it: coffee dates are not romantic, inspiring or memorable. But they have the same effect as limited primping: lower expectations. Plus you can bail quickly if it is a disaster. Save the razzle dazzle for date #2.

CAUTION: If he takes you on an overly fancy first or second date, he may be a douche trying to woo you in exchange for sex. If he busts out family photos via cell phone or PHOTO ALBUM he is trying to lower your defences for sex (been there twice with two insincere guys and ewww).

  1. If it is meant to be you can’t screw it up even if you tried

Yes, I just finished rhyming off some rules and tricks of the trade learned through trial and error and now I’m going to say this: If something MINOR turns a guy off and make him run for the hills then he wasn’t meant for you.

Someone will come along and be delighted by your quirks, even if your “quirks” involve falling flat on your face or divulging too much personal information on date #1. When it is right, things will just unfold naturally.

Vanessa blogs at www.daremytruth.com about her screenwriting journey, self discovery and relationships. She abuses brackets, gives too much information and uses cultural references like they’re going out of style.   

What do you guys think of Vanessa’s dating commandments? 


Latest pins

Pinterest widget in section "Footer Full Width": Setup not complete. Please check the widget options.