Guest Post: How I was an asshole the day before Valentines

So I’ve been relationship single for about a year, had a bounce around but that went to the side. My bud tells me that maybe I should try Match or something, so WTH I ‘giver a shot.

Girl chats me up on there talking how she likes a lot of the stuff I do. Sleds, 4-wheelers etc.

She was pretty cute, my picture was on there too so she knew what I looked like and it was a recent pic. Anyways we agree to meet. I let her know I gotta wake up early to help on a friends farm in the morning and I will have some hydraulic rams for his skidder in the box of my truck.

I agree to take her out to a nice steak house in my area, I am talking $50 tenderloin place and $5 drinks. She knows the place and is all exited saying she went there when she was a kid and knows they have awesome steak and its been a long time, so in my head I am thinking this is gonna go good.

Well she rolls up in a brand new Buick or something all cleaned up and mind you its -20 outside. My PSD (power stroke diesel) is rattling away covered in road salt. So I am feeling like an ass already.

I jump out and say “You ready to get some steak?” She says yes and we start rolling out, its a good 30 minute drive but she starts giving me the clues right away “how shes tired” and “tomorrow is a busy day for her” then starts in with saying opposites of what she liked before……..

So at this time I am just like WTF am I taking this broad out for?  I turn the truck around and start heading back the way we came. I know the side roads so she asks “how far is this place away?” I think she was wondering WTF was going on but she wasn’t gonna say it.  I kept it calm and cool asking about her kid and all that, then about some local racing she liked to watch.

I come in through the backside of where I picked her up and she realizes that were back where I picked her up.

She asks “why are we back here?”
I tell her “since you keep saying how you’re tired and you got a big day tomorrow I think I am just gonna make sure you get the sleep you need and get a good start for tomorrow”.

She looks right at me, with some evil eyes and opens the door and gets out.

I leave and go to the steakhouse that I was gonna take her to.  Spent the money I was going to spend on her on Captain and Root beers.

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5 Types Of Toronto Women

The landed world traveler

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She literally landed from you-name-it within months or even weeks.  Australia, anywhere in Europe, Asia, middle east, helping starving kids in Africa, whatever else and even next door US.  She has many stories, nothing crazy, but has chosen Toronto to settle and start a family.  Except it’s not that simple honey.  I am usually one of their first realizations to this – never the last.  I avoid them now as they are usually worse than re-bounders with their false timelines and expectations.  This person lives in a bubble.

The Lawyer

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Oh the lawyers.  From recent grads to juniors and  law firm partners, I’ve met them all on dates.  It’s funny too, as the partner is far more relaxed and open than the junior is.  Almost all agree that they bit off more than they could chew and seriously hate the job.

The born and bred city girl

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Not many dates with this one, they tend to repent me.  I grew up bouncing between south western Ontario and Muskoka, a “country boy” if you will and the city chicks don’t jive with it, nor do I with them. Include Oakville.

 

The non city girl

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This is the one I have the best success with – All surrounding towns and cities are open season, as close as Milton to the west, Pickering to the east and Bradford to the north.  They are so much more real, legit and free.  Canadian country boys also have a deep unknown bond and connection with southern girls from the US that needs further exploration.

The work bitch

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When I moved to the city back in 2008 I couldn’t fathom the amount of workplace back stabbing, bullshit and distrust among people in the corporate workforce.  And after a few years you could pin it on one or a few bitches.  I’d call them out on their bs routinely – these are deeply disturbed idiots acting out and disrupting  entire companies.  Anyone that has worked in an office knows who I am talking about.

That aside – they are also single and dating (imagine my surprise).  The feeling is weird when the work bitch from another company is now in hot pursuit of you.  Remember opposites attract, or better sense, polarity attracts.  They usually have severe daddy issues, bang on the first date and stalk when you don’t call back, you’ve been warned.

 

 

 

 

 

The Hot Pants

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I am a sucker for girls that wear shiny tight black leggings, big time, and when she walked in wearing them I couldn’t have been happier.  I ordered a beer, she wine and then we shared a huge plate of nachos and cheese.  I had big plans for this one, but nearing the end of the date she told me how she absolutely does NOT kiss on a first date and how she had squirmed away from the last guy that tried.

Ugh.  Structured.

“Maybe the cheek”

I won’t say the conversation was all that great, all she really talked about was her mundane job (in an attempt to glorify)  and she had a really low overall energy about herself.  I did manage to make her laugh and loosen up but she was low energy at the core.  I also didn’t get to indulge in her hot-pant glory as we were in a booth and she never got up – so I knew what to plan for date #2 after giving her a peck on the cheek at the end of date #1.

We would play pool!

I set the date up at a pool hall / bar / grille in an attempt to make things more upbeat and active as 2nd dates should be, my hopes were soon dashed.

She showed up looking like she hadn’t slept, or dare I say showered in a week.  Her done up hair legit looked greasy.    All pool tables were being used so we were once again stuck in a booth with her going on and on about her job while nearly putting me to sleep.

Conversation sputtered along until I got the bill and we left.  In both cases her uber driver showed up within seconds killing my end date kissing game, but I did manage to plant one on her willing lips at the end, but I knew this one was D.O.A.

The next day I received a text thanking me for the nachos but she wasn’t feeling the mutual chemistry that we should be at this point and I was quick to agree with her.  I love not having to be the schmuck – and wished her all the best.

Without her telling me of her structured rules I would have kissed her passionately, or at least tried, at the end of date #1 and only one of two things would have happened.  She would have enjoyed it, or cheeked me.  If she enjoyed it, date #2 would have been much more interesting and if she cheeked me it would have been over right then and there.

 

The Hot Momma

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I’ll be straight, I really don’t date women with kids – not because I am against it, it’s because most of the single women around here simply don’t have any.  But way back when I started this journey I went on a 2nd date where my date brought her 5-year-old niece and we went ice skating, where I promptly ended up having more fun with the niece than I did my date! (I helped her learn to skate better and was then greeted by about 100 women within a mile on how cute me and my “daughter” were)  So I have always been open to the idea, it just rarely presents itself.

We met on Match and where it says kids yes/no it just said yes – which means one kid, if there are more it’ll say 2, 3 – whatever.

We met for wine and tapas – she was gorgeous and we had amazing conversation.  But this was where I learned that she had two kids.  I didn’t let that get in the way of our nice evening together though.  She said that she had tried dating a year before, but it was too soon after her divorce so she took more time to herself – which I commended her for, nobody likes a re-bounder 😉

We then went to quiet pub and snuggled into a booth for pints, it wasn’t long before I was on her side and you can assume the rest.  No I didn’t bring her back to my place.  She said we could do that next time, but I would never do that to a single mother without full intentions of a relationship, so after a few pleasant texts we drifted apart and a week later I deleted her phone number from my phone.

The Hot Pizza

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I believe this particular sassy brunette was all but finished with online dating, like most people are in the waning months of a dating site subscription left to linger.  She would take literal days to reply until finally offering me her number as she flat-out “never checked the dating app anymore.”

Been there.

From there we agreed on a pizza date at a place I had never been to before.  We met inside the place and she was well presented.  Perhaps her photos were 3-4 years old but nothing to complain about.  The only thing I can complain about was the pizza.  It was essentially hot sauce, cheese and honey – yes, honey.  Between burning my mouth and lips I also had sticky fingers.  I hate all 3.

From there we went to grab a drink at a really cool bar and we had a great conversation filled with laughs.  This wasn’t like a date, it was like a reunion with that friendly acquaintance that you only use to chat with in the high school smoking section and nowhere else.

Before parting ways we kissed and she said “let’s do this again soon!” and I agreed.

I even set the date for the following weekend, but I truthfully wasn’t really into it after a few days had gone by – while we indeed had a good time I don’t think enough was there to warrant the work involved with meeting again .  The morning of, like she was telepathic, texted me a cancellation saying that after work it was just too much to head back into the city and that she just wasn’t up for it.  I respectfully let her know it was no problem at all and to take care.

Second dates should only happen if you had such an amazing first that you can’t wait for the second and can’t stop thinking about the person  – not out of boredom or “what if”.

The Curvy Blonde

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We met for a coffee in her part of the city and while our conversation flowed nicely, I wasn’t sure if I was all that attracted to her.  After coffee we went to another spot for food before I dropped her off.  A few days later she called me and asked if I would like to see her again – I said sure and set a time that I would pick her up and we would drive around and find a spot to chill at.

The reason I was more or less open to a 2nd date with her was because she stayed all covered up during the 1st and I really had no idea of what type of body she had and I wanted to see the goods.

Date day arrives and I drive to pick her up, meeting her at her front door.  We drove to a busy part of the city, parked the car and walked until we found a weird little hipster paradise that managed to screw up simple bacon and eggs.  Highlight moment was when she managed to spray her entire front-side with hot sauce while trying to get it to come out of the bottle – it looked like a crime scene and smelled absolutely horrid.

After eating (and her cleaning herself up with 400 napkins and a few trips to the ladies room) we left to go for another walk but soon ended up back at her place.

We had tea and watched TV but she made it clear that her bedroom was strictly off limits!  We kissed and played around before I called it a day and went home – knowing I wouldn’t be seeing her again.  She had a very structured vibe about herself and a little controlling which I don’t like.

She texted a few times before I told her there just wasn’t enough chemistry – just not enough click.  She rebutted that clearly all I wanted was sex and I just deleted the message.  No, I don’t go out on two dates with you, pay for everything all in the weak attempt to “use you” for sex.  If I wanted that I would have met her again, but I am not here to waste anyones time, including my own.