50 First Dates—First Date #11 & #12: Online Dating in Calgary

Dating in Calgary — Looks vs. Charisma: Who Wins?

The first afternoon I move into my new pad in sunny Calgary, Alberta, I go on a date because online dating in Calgary is fun, right? Riiight? 

(By the way, there’s a coupon code somewhere in this long, but informative, post!)

Let’s backtrack just a smidge …

A few weeks before I’d moved to Calgary, when I was only contemplating moving to Calgary, I’d signed up to match.com to check out the Calgary cowboy scene — not that dating in Calgary or the supply, or lack of, rugged, cowboy-hat-wearing male specimens would influence my decision (much).

Anyway, there was a dude on Match that was just my (old) type: Tall, Dark (haired), and Handsome. With blue eyes, my weak-in-the-knees-ness.

Dammit, I’m shallow. *Shrugs, moves on with her life.*

So, I start chatting with TDH via Match, and then we text. I discover he’s originally from Vancouver Island just like me! Instantly, I feel a familiar connection.

Dammit, I’m normal. Ish.

Back to the day of the first date …

After a mix-up of him thinking I meant meeting on Saturday (I was a no-show) when, really, I meant Sunday, I arrive at the date destination in sweats and stained sweatshirt with virtually no makeup on — I just spent the afternoon moving, y’all, come on! — and sit hoping he shows up.

I’m early so I buy myself a bran muffin and decaf breve latte.

Shortly after and on time, he arrives via motorbike, as evidenced by the motorcycle jacket and helmet, which by the way, fellas, is damn sexy even if a girl don’t ride. (Side note: Though I actually do have my motorcycle licence, which you can read about here, I’m emotionally equipped to ride in the side car only.)

We sat in the cafe dining area where servers are on the ready to refill water glasses, which they did ― regularly. TDH Motorcycle Man (MM) didn’t order anything.

I’ll get to the significance; I promise.

We chatted and chatted, I learned that TDH MM wants to retire somewhere warm, like Thailand or South America, where he can “stretch his pennies.” (Also significant! I’ve spent enough time travelling “developing countries,” which you can read about here, and I certainly don’t want to live in one. I loathe the feeling of sand on my feet and laying around on beaches. The penny-stretching we’ll get to.)

After a couple hours, I claimed fatigue (mostly true) and bowed out, gave him a hug and said, “Text me.”

I went back the next day and gave that server an extra tip.


Because we, TDH MM and I, had sat there for two hours — two hours, people — a relatively long time for a server to provide commendable service … for which he didn’t get compensated by TDH MM, because he didn’t order anything. (I’d already tipped at the checkout for my items.) TDH MM either didn’t care or perhaps didn’t think about that fact. Not cool, folks, not cool.

But I figured maybe TDH MM was nervous and forgot his normally decent dining etiquette, so I cut him some slack and agreed to meet him again.


But before that second date could happen …

I had been trying to sort through my emails on Match, because if a woman on a dating site with decent photos and a spectacularly written profile, ehem, like mine, is gonna get emails, again whether she’s dating in Calgary or anywhere else.

Actually, let me rephrase that: If you’re a woman on a dating site with a half-decent photo, you gonna get emails. (But the quality of those emails will vary depending on your photos and written bio.) Which brings me to …

I don’t normally recommend anyone read every email.


Simple: it’s a waste of time. And wasting time on dating sites is why so many people get frustrated on dating sites and get off them. So, instead, filter filter filter first.

Also, I’ve learned that, most of the time, men would rather be ignored than get kindly rejected. And their egos get even more bruised if you try to pass them off to “a friend who would be just perfect” for them. Yes, passing them along makes them feel like “cheese on a cutting board.” #oops

Where were we? Oh, yeah, don’t answer all emails …

Well, because I had put my career notes in my profile, I thought I should read every email in case someone was asking a business question. Bad idea! Refer back to “too many emails!”

And because of too many said emails, I end up accidentally going on a date with Legal Matters

Again, I’ll just cut to the Cliff / Coles Notes, Legal Matters was:

  • an inch shorter than he’d indicated in his profile. Guys, you can round up by half an inch max, otherwise you’re either delusional, deceptive, or down on yourself for vertical lacking, none of which is sexy.
  • a little too keen to go down the naughty road when prompted. Yes, there has to be sexual tension, but excessive sexual reference only makes you look way too damn horny, which is not sexy.
  • a dad. Wait, what? How’d I miss that?? I explicitly wrote in my profile — in my Top 5 deal breakers section — no kids! That miss was totally my fault, however, because if a guy’s gonna try to get the girl and even if her deal breakers are written in ALL CAPS, if she says “yes” it’s her (my) own fault for not filtering! And, in his defence, I wrote, “wee ones” not “offspring,” and at least one of his seedlings is a teenager.

But here’s where Legal Matters gets credit, he:

  • was uber confident, but not cocky, despite being vertically challenged according to my shallow needs. (He probably doesn’t even realize he’s not 5’10”.)
  • took the lead. “Do you like mussels?” Me: “I like everything.” He ordered the mussels. “Do you like beet salad?” I repeat myself. He orders the beet salad. He also plated for me while asking if it was okay if he plated for me.” My answer: “Yes, please do!” Women love men when respectfully take charge.
  • asked what kind of wine I like and ordered it for me without asking the price or checking the menu. That’s fucking impressive. If you have to check the menu for price, you’re at a dining establishment that’s out of your league. Bad choice because checking prices tells her you’re either cheap or wondering if she’s worth it.
  • moved us to a quieter table, when one came available, where he could sit beside me. Smooth move because it was then easier to appropriately and frequently touch me — on my arm, my shoulder, my hand. Smart man. Physical touch is intimate and affects the sexual (chemistry) area of women’s brains.
  • picked up the tab without waiting to see if I’d offer to pay or go Dutch, even after I’d blurted out (early on), “What?! You’ve got kids? That’s a total deal breaker. Shit.”

Note: I offered to buy next time, as friends. I always feel appreciative when a man buys me dinner but also guilty for not giving anything back. Pay attention to this: If I buy, you are now forever in the friend zone. Period. In my world, a man pays for food outside the home, and I pay for food inside the home.

Bottom line: If I didn’t know my deal breakers, Legal Matters might have swayed me.

And don’t be trying to change my deal breakers. My deal breakers are mine. You have yours. If you don’t like mine, then we’re not a match. Whew, good to know. Next.

Okay, so in taking my own advice, I decide to give TDH MM a second chance. We meet to do “the stairs” and then a walk.

We do both. The conversation flows but, at least on my end, it feels less connected. He doesn’t notice because I have naturally amazing people skills — perhaps from 20 years in sales — and every guy I’ve gone on a date with tells me that he’s “never opened up like this before,” so we know that I’m the devil. But whatever. It is what it is. (I am what I am: innocently devilish.)

Here’s what confirmed my sorry-it-ain’t-gonna-happen-with-you decision. TDH MM:

  • oops, left his wallet in his vehicle. Always be prepared, fellas.
  • let me pay for his latte — that’s fine … friend — but didn’t offer to get next time and wasn’t chagrinned at all about a woman paying for him even though he makes at least three times the income I do and knew it.
  • didn’t lead, didn’t suggest, just followed along with whatever I wanted to do. I’d suggested every point of each date. Sorry, but women like leaders. Wait, let me rephrase that in “man words”: Women have sex with leaders.

What Have We Learned About Online Dating in Calgary?

  1. Women like leaders, whether you’re dating in Calgary, London, or TimbuckNowhere!
  2. Sustained eye contact triggers sexual chemistry.
    Whether you like it or not, you’ve got to have a strategy — but not a manipulation strategy.
  3. If you don’t want to waste your pennies on dates that go nowhere, filter better!
  4. Tall dark and handsome is no contest compared to short, fat, and balding if the latter has “sexual chemistry strategy.” To be fair to Legal Matters, he wasn’t that short and was barely balding and not fat, but the exaggeration makes a bigger impact. (If I had to choose between them, I’d take “children” over “cheap.”)
  5. Online dating in Calgary is no different than online dating in any major city! (I’ve personally done it — online dating — in Vancouver, Victoria, Seattle, and Los Angeles, so I speak from firsthand experience!)

So, anyway, I’ve edited my written profile based on my research (i.e., reading all those emails) and now only look at the ones who actually “qualify.”

I don’t want all the potential mates, just the right one — a dating strategy you might want to consider. And since this city is covered in snow for half the year, yes, online dating in Calgary is an efficient way of finding singles.


p.s. If you want to know how to get game, aka have a strategy that is actually attractive, get my GET A GIRLFRIEND program. 50% OFF FOR NOVEMBER ONLY: USE COUPON CODE: MOVEMBER

p.p.s. If you just want to get decent replies (any replies!) online then check out DOUBLE YOUR ONLINE DATING TRAINING.

About the Author Anna Jorgensen

Vancouver Dating Coach for Shy Guys & Introverted Men. Matchmaker Liaison. Founder: Wingmam

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