Four women in four cities take on 365 dates between them. Follow their adventures and misadventures.

38. Playing Your Cards Wrong – Mr. Gambler

Mr. Gambler wore shiny patent leather shoes, white tight jeans and a white blazer on our date. He looked rather out of place next to the regular folks in the bar.

I used all my facial muscles to hold onto my smile – fearing I would break out into laughter. I must have looked rather odd, because he asked me, “Are you OK?”

“Oh yep, yep I’m fine, how are you?” trying to look normal again.

I looked down at his shoes – real Louis Vuitton! In no way am I a label snob (after all, I shop at op-shops, but this boy had some killa designer threads.

I looked down at my old, scuffed work shoes and frowned to myself.

Must buy new shoes!

Mr. Gambler was not particularly tall or good-looking, but he had boyish charm. I noticed he found it hard to make direct eye-contact and seemed a little nervous sometimes, but I was very persistent!

“So what are your plans for the weekend?”

“Oh, I’m thinking of flying up to Melbourne tomorrow,”

“Cool what are you doing up there?”

“Just going with some mates.”

“Oh cool, what are you guys doing up there?”


“Ah well, we…my friends and I like to participate in recreational card games…at the Casino…you know, just for fun.”

I proceeded to confess that I am not much of a gambler and mention that I do not know anything about ‘those pokie machines’…

“Oh, really? You wanna have a go?”

He got up out of his seat and indicated for me to follow… I could not believe we were going to play the pokies.


He sat down, put all the money in while I stood next to him to ‘watch’. He was explaining how the game worked, but I tuned out:

1. Because I had no interest in playing the pokies, and

2. Because he showed no interest in me. I mean not once did his eyes leave the brightly coloured screen.

When he had used up all the cash in his wallet, he turned to me:

“Ha, I better stop now.”

No shit!

I am not sure how much money he had wasted, but I saw quite a few 50 dollar bills being pulled out. When the bill came, I snatched it off him and paid for the full amount. He acted all upset:

“Omigod, I can’t believe you did that, I have never, ever let a girl pay for me.’”

“Well, Mister, it is 2011, it’s not the 1950s…relax.”

I just wanted to show him that just because you have money, you do not need to flash it or waste it.

Before we went our separate ways, he told me that he thought I was a cool chick because I played the pokies with him.

I did not! You played by yourself!

“Cool maybe we can hang out again sometime… you could come to Melbourne with the boys, it’ll be fun.”

“Oh cool… yeah maybe…”


What do you think? Have you ever dated someone with a gambling addiction?

Have you ever been taken to the casino or pokies for a first date?


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