Surely That’s The Moment You Made Your Exit From This Awkward First Date. Incorrect.

“I don’t like you, but my bro does, here’s his number”Boring (and kind of rude) Bro

“I can’t stop touching my hair because you make me nervous”McDreamy Bro

I like writing about dating because it’s quirky, fun, and uncomfortable. My stories make my friends in relationships hug their guy a little tighter that day, and make my single friends join in with,


Everyone takes different paths when it comes to dating. Some people date one guy from high school, and end up together. Some people go on 30 first dates in a year (what? who? me? no?).


… So I have gathered a LITTLE, “awkward dating” material.

If the idea of going on a first date makes me feel uncomfortable, I like to force myself to go regardless. It’s a good way to grow your confidence, and sense of humour.

Anyone that knows me, knows that I am a sucker for a bro in a navy suit, with brown leather shoes. I associate this outfit with passion, intellect, success, chivalry, and overall charming-ness. Before I left for Ottawa, I told my girlfriend/coworker/person that I miss dearly that if anyone needed me I could be found on parliament hill drooling over the men in the navy suits.

So, when bro in the navy suit asked me to meet him (and his friend?!) for a Saturday afternoon drink, I said yes (YES even though he said he was going to be with another bro). The suit blinded my judgement.


This is how it went down.

I entered the restaurant from stage left, bro and bro’s bud were on stage right. Bros were sitting opposite from each other. So, in my entering panic, I took the closest seat, next to Bro Third Wheeling Our Date. 

WELL, bro I was on said, “date” (if you can even call it that) with, was unimpressed with my choice, and made me move to the seat next to him (Ok? It’s been 5 seconds and you’re already telling me I did something wrong).

We all make our introductions. The bros are all dressed up because they were at the wine & cheese show (an event that he had asked me to be his date at, to which I had refused). I am now thanking my lucky stars that I had declined this invite, as you could cut the tension with a twinkee (you don’t even need a butter knife).

I’ve been there 3 minutes, and I can already tell this is not going to go well. While I’m considering my exit options, his friend fixes the tension by talking about the Red Hot Chilli Peppers (nice move Third Wheel Bro, everyone loves the RHCP, this SURELY will get all of us talking).


Navy Suit Bro, doesn’t like the Red Hot Chilli Peppers.


Not only that, he goes on to tell us that he doesn’t actually like music at all.


Not rap, not country, not jazz, not classical, NOT top 40. No music. Ever.

Now, because I have a sick way of deliberately making an awkward situation worse by addressing the GIANT FUCKING ELEPHANT IN THE ROOM, I use this moment to segway into,

“… Soooooo I work in the music industry” – Gives No Fucks Girl.


Laughter ensues from Third Wheel Bro. Navy Suit Bro does not crack a smile.

As you’re reading this, you’re probably thinking, surely this is the moment that you made your exit.



I didn’t want to be RUDE to the man who demanded I spit my gum out (and held a napkin up to my face until I obliged).

IDIOT (me).


I was able to stay because his bro was actually pretty witty, and made the awkwardness bearable.

We decided to play a game (the name of it is escaping me, but you slide a thing on a board with some pucks and salt and you casually let the guy win every time because you’re non-competitive like that).


Navy suit guy (bro sorry) did NOT enjoy how well Third Wheel Bro and I were getting along. I wasn’t interested in him, he was just a truly decent human being.

Navy Suit Bro whose name we are now going to change to Boring (and kind of rude) bro decides to pull a Houdini on us and motherfuckin’ disappear, WITH his jacket. So I’m sitting there, pointing out the obvious,

“He took his jacket, maybe the bathroom is chilly”.

“Haha maybe” – Third Wheel Bro


“He’s not a smoker is he?”

“Ummm.. nope haha.” – Third Wheel Bro


“WELL THEN, I suppose I will just leave?”

“If you want… this doesn’t seem to be going well.” – Third Wheel Bro



**starts putting jacket on**

Of course, this is the PERFECT moment for Houdini to reappear, as I’m getting ready to bail without so much as a goodbye.

“Oh you leaving?” – Houdini Boy Who Can’t Hide The Lack of Disappointment On His Face

“Yeah uh, nice meeting you, bye”

**Does the awkward hug**

… I am not 2 minutes out the door, when my phone buzzes.

“I don’t like you, but my bro does, here’s his number, 416-go-live-happily-ever-after-and-die” (so I altered the last few digits a bit).

At this point… I’m offended and feeling complimented all at the same time. I see no future with Third Wheel Bro, but I have the urge to text him merely to say,

“… Seriously guys? What the FUCK just happened”.

I believe I read the text on my walk home, and loudly pronounced,


Birds flew out of the trees (no they didn’t but that would have been cool. Mostly I made a homeless man jump).

Fast forward three months or so later, to this past Friday night. WHO DO I SEE, but motherfuckin’ Houdini (in said Navy Suit – is that all he owns?).

Oh it gets better.


He isn’t alone.


I know, I was there!

Not only that, she is basically having sex with him in front of all of us. It looked like the Nicki Minaj anaconda video.


I couldn’t look away.

She could get LOW.

He was absolutely loving it.

I was shoving all of my friends in front of me while I curiously peered around their body to watch this car crash unfold.


“Is this real life?!”

Yes it was, my friend’s guy friend on crutches was also across the room motor boating a stranger’s tits.


This was very real.

I ate a poutine the size of my head and tried to forget what I saw.

All was well in the world again.


… for the most part.

– Kails







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