A Betting Man

Posted on 2019.05.13

This client is one of my favourites. Older gentleman who lives a fairly simple life. In his line of work, there are multiple networking events which he hates going to. To entertain himself he brings me along specifically to drive one person up the wall. This one person is his rival going all the way back to university. They competed to be top of class, then competed for internships, and even after that, competed against each other while working at different firms, Every month, they bump into each other at least one networking event and do their best to one up each other.

More business. More toys. More praise. About a year ago, my Client realized that he had an ace in the hole: a Companion. Tired of hearing his rival express fake sympathy about the end of his marriage (long story short: she got a LOT in the settlement), my Client decided that at the next event – a fundraiser – he would bring a date. But not just any date. The kind of date that his rival could only dream of. His rival was still married, but not happy. But apparently, he wasn’t the kind of man who would step outside the boundaries of his marriage. His wife didn’t seem to enjoy their marriage either, and I was told that to see the two of them at an event was to witness two people be absolutely miserable in each other’s presence.

The first time I met my Client, we met at a bar near the venue, where he explained the entire rivalry, the unhappy wife, and some of the shady things his rival had done to him over the years. Normally I’m not a petty person, but once he gave me the entire backstory and the goal of our date, I was all in. We finished up at the bar and made our way to the venue. As we walked in he leaned over and whispered, “I’ll follow your lead. Have as much fun with it as you want to.”

Game on.

The theme of the event was “Old Hollywood”. A sit down dinner, silent auction, and a little bit of dancing after. As we made our way to our table, I realized that there was a man staring at us from one of the tables nearby and staring HARD. I glanced at my Client and see he’s smiling and waving at the staring man. As I’m being seated, my Client leans into my ear and whispers, “just for the entrance alone you’re getting a tip”.

Between the first and second course, the rival stops staring makes his way over to the table for an introduction. He brings along his wife and the three of them exchange the most unfriendly “friendly hellos” I have ever witnessed. The two men traded a couple of bad jokes back and forth and halfway through a third bad joke, the rival stops mid sentence and says to me, “he’s boring! Tell me what you do.”

I smile and explain that I’m a student (true) majoring in anthropology. The rival laughs condescendingly and says to me that I’m going to have trouble getting a “real” job with my undergraduate degree. The smile fades a little when I explain that I’m actually working on my master’s and spend quite of bit of time doing consulting work in the area. His smug expression morphs into one of confusion when I explain that I specifically study ethnographics: traditional media, popular culture, and digital media have converged into this never ending flow of information and discovery. The unhappy couple returned to their seats and my date takes a moment to bask in the glory of his first win.

“I don’t understand what you just said, but I know he did, and I love it. I see another bonus in your future.”

I gaze adoringly at my partner in petty crime and laugh. I start to feel adventurous and ask if he’s interested in a side bet: if his rival tries to hit on me, he has to double my bonus. If he doesn’t, I only get to keep half the bonus. To anyone observing, we look like a couple having way too much fun, but to hear us is to overhear two kids coming up with the silliest of rules.

If the rival buys me a drink, it doesn’t count. But if he touches my hand it does. If he asks for a business card, he’s not hitting on me. But if he asks just for my number, he is. If he asks me to dance, he’s not hitting on me. But if he cuts in on me dancing with someone else, he is.

We agree on the rules but shaking hands seems too formal – plus we know the rival is watching us – so when he suggests we pinky swear on it, I laugh and hold out a perfectly manicured pinky to lock in our bet. I’m fine with the rules because I always play to win.

An hour goes by and the rival is obviously jealous of my Client and all the fun he’s having with me, but he won’t act on it; he won’t try to do him one better. He doesn’t ask me to dance. He doesn’t try to get my number. Nothing.

I break away from my date on the dancefloor and make my way to the ladies’ room. I freshen up and stare into the mirror, trying to figure out what I can do to win my bet. I get so lost in my thoughts that I don’t realize the woman standing beside me at the sink is the rival’s wife.

She clears her throat and I snap out of my trance. She smiles a tight smile and asks if I’m having fun. I confirm that I’m having a blast (true) and ask if she’s enjoying herself.

“No. I’m not. Every time we go to one of these things I have to watch my husband try to be everyone’s best friend. It’s tedious. But you seem to be enjoying X’s company?”

She phrased that last part as a question. I confirmed that I was enjoying X’s company and should head back out to him.

“Why? We could just stay here…”

I turn away from the mirror and face her. She smiles her tight smile again as she looks me up and down.


So I am getting hit on. I’ve been paying attention to the wrong rivalry.

“I’ll be honest. My husband and I have a bet every time we come to these things. Who can take home the most beautiful woman? We try not to pick from our friends because they just wouldn’t understand. But there’s always a beautiful new girl behind the bar. Or a waitress. Or even another guest.”


I politely decline and we make our way back to the party. As we part to go to our separate tables, she hands me a business card and says, “think about it”. When I return to my Client, I take him out to the dancefloor for a slow song and whisper the truth in his ear.

He stops and pulls away from our embrace and I tell him that I slipped the business card in his pocket as proof. He checks and of course the card is there. His smile gets wider and he says to me,

“Double or nothing?”

Photo by Pexels

Newsletter subscription

Be the first to know of Cupid’s exclusive news, including arrival of new ladies
  • This field is for validation purposes and should be left unchanged.

Get in touch


Cupid's Escorts
Toronto Escorts Cupid's Signature Angel
Office hours

352 Front Street West, Toronto M5V 0K3





Newsletter subscription

Be the first to know of Cupid’s exclusive news, including arrival of new ladies
  • This field is for validation purposes and should be left unchanged.