Dating Confessions from YYC: Speed Date Edition


How my friend Blaire spent her December.

What happens when you go from a three year relationship right into a seven year relationship and then a decade later find yourself single in your late twenties?  In my friends case, she decided she had a lot of catching up to do. Because of her growing and busy career she also knew that she didn’t have time for this.

If you’re nineteen and single you have all the time in the world to experience anything you want. When I was nineteen I was living at home, skipping my university lectures, and filling my time with friends and boys. I spent endless hours in the loft above the cafeteria wasting away my days. Plenty of time to date all the losers I wanted, get my heart broken a few times, and pick myself up again.

When you’re twenty-eight and single things are a little different. Blaire has a growing business, way more bills than she did a decade ago, and frankly isn’t interested in dating all of the characters one might find in her early twenties. Plus she was still missing her ex and grappling with the question, “How do I know he wasn’t it?”

You could say what Blaire decided to do was go speed dating.

She was in search of a few things. Some clarity would be nice, but she also wanted to check some things off of her newly single list. So this is how my friend jam packed a decade worth of experiences into one month.

Blaire started things off with a bang. She was front row at a comedy show in late November. She recognized the comedian because he’s in one of the most relatable films of our time, The Hangover. I received a text from her the next day.

“First one night stand executed.”

Way to get back out there girl.

“I also got my celebrity card.”

Like, at the same time?


[insert shocked/proud emoticon faces here]

I don’t know how one goes about catching the attention of someone on stage, especially a celebrity, but Blaire must have done something right. She even handled the aftermath perfectly. A one night stand is a one night stand. She refused all other offers and went on her merry way. Right into the arms of a forty something billionaire.

I’m not even kidding.

“15 years ago I would have married this guy. He wants to fly me to Cabo.”

And you’re not going???

“If I go I’ll feel obligated to sleep with him and I can’t bring myself to do it.”

Fair. But, billionaire…Cabo…you could use a vacation….

“I can hardly stand making out with him.”

Apparently the old guy was quite persistent. Luckily Blaire was so busy that even the temptation of a free trip to Cabo couldn’t convince her to pick up and leave. A few weeks later Blaire was hanging out with the buddy. As she was walking him out one morning they bumped into old man’s friend in the elevator. This was when she stopped getting exotic vacation offers.

So who’s the buddy?

“Just this friend. We were drunk and decided we should hook up. I think he might be gay.”

What makes you think that?

“We’ve had four cuddle parties.”

Then Blaire told me about the athlete. As in Olympic athlete.

Oh an athlete! That’s exciting-what’s he like??

“He’s painfully sweet and polite.”

That’s good! Chivalry is dying they say.

“He’s also shorter than me and bald. Those are two of my non-negotiables. And picturing him going down on me makes me want to die.”

She gave the painfully sweet olympian the old college try but couldn’t bring herself to keep seeing him.

At this point I think Blaire is almost finished.  This is already more guys than I’ve dated in the last year.

“Okay so after the athlete I met the philanthropist. It was very Sex in the City. We met at an art gallery and he was wearing a skinny tie. He was very intriguing. I could see him sizing me up and down but when he asked me to go home I said no. I had already had a very busy month.”

I’d say.

“We talked business all night. Great conversation.”

On their first actual date he continued to insist she come over. Blaire continued to say no but quickly realized this guy wasn’t taking no for an answer.

“He really wanted to take me down.”

Eventually she let him come upstairs: “He was the WORST KISSER on the planet”.

This is another one of Blaire’s non-negotiables. I actually think it’s a universal must-have. If you don’t enjoy kissing each other you’re doomed. In her words, he continued to rape her phone for a few weeks. He was the oldest of three brothers with no long term relationship experience. Far too many red flags.

“Before I tell you about the big banana I forgot about one more guy!”

You’ve got to be kidding me Blaire.

“No seriously. There was also a millionaire. But he was shorter than me when I had heels on and had way too much gel in his hair.”

Then Blaire finally told me about the guy I was waiting for. The one that got under her skin. He was another friend. You can guess as to why she called him the big banana. “I’m obsessed.”

The problem was that Blaire and the big banana had a mutual friend who was warning her to run for the hills. This friend knew six girls that had been “destroyed” by banana. Classic damaged-goods story-now he just uses and abuses. Her last words to Blaire were, “And whatever you do, don’t let it turn into casual sex”.

Too late.

Of course of all the guys she met this month, Blaire was obsessed with the one guy that she shouldn’t be. He ticked off all of her must-haves. The physical ones that is; tall, sexy, and a full head of hair with not too much gel in it.

“I check my phone every three minutes for a message from him. I’m too busy for this.”

Most of us would probably give the advice to stay away from the big banana.  But when you’re the girl into a guy like him, you give him the benefit of the doubt. Whether we find ourselves in this situation at nineteen or twenty-nine, there’s something about this guy. In my opinion, we’ve watched way too many movies where friends-with-benefits turns into true love. I blame Ashton and Natalie Portman for putting these crazy thoughts into my friends head.  I suppose there’s a possibility that Blaire could be the girl for him: the one that mends his damaged heart, the girl he couldn’t let go of. Only time will tell. All I know is that anytime I’ve met a big banana and stayed around to enjoy it, things ended ugly.

Stay tuned.

A true story.

By Kylie King

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