How to be “cheeky”.

How I managed to con a con artist.

How to be Cheeky
How to be Cheeky

It had been a while since I had been a part of the dating scene. Newly single and afraid of diving back in, I had held it off. But, as expected, I was tempted by the intrigue of Tinder; meet new people, find singles in your area, there have been Tinder success stories before, so surely it would work out for me. Maybe.
I tried not to look for Mr. Perfect right away. I let the age range go a little over and a little under my ideal, I swiped right on guys who weren’t exactly my type, have some flexibility, I thought.
I guess I had it coming.
The guy in question was named James. Blurry photo that made him look like he had potential, beer in one hand, a mate in the other. A little pudgy a little more…bogan, if you will, than I would usually prefer. But he was polite, friendly and seemed to be interested in me.

We spoke for a few days. Talked about new movies, sports (his love of AFL) and our jobs. Eventually, he offered we meet, and I obliged. This was the first date of three that we would end up going on.
The night was slow at first. James’ talk of etiquette and chivalry seemed to be only that: talk. He sat with his legs spread, belly sticking out, and spoke with his mouth full. But I tried to stay positive.
Once that first bill arrived, an awkward silence filled the room. And being the polite person I am, I felt inclined to fill it. I offered to pay. James was all the more happy to accept this, so I pulled out my card and did the deed. But James had one request.
“Would you mind driving me to the train station?”

No car? I smiled, and obliged. It was only a short drive away, anyway. He thanked me, gave me a kiss on the cheek (followed by a delightful spout beer breath all over my face) and headed over to the platform.

The next day I received lectures from my friends saying I shouldn’t have paid. How he should’ve at least offered 50/50. How he better pay next time. I laughed it off. By the afternoon of Monday, I received a message from him.

Thank you so much for paying the other night.

I want to repay the favour.

Why don’t you come down my way and we’ll catch up again, my shout?While I wasn’t one to hold onto “pay backs”, I was still intrigued by the offer. Yes, it was my own fault for offering, but I was still delighted by the notion of someone treating me.


The night couldn’t come by quicker, and after a long traffic-heavy drive into his side of town (30km out of the city), I finally reached the restaurant. James was waiting at a table, his cocky smile greeting me from the door, his pudgy belly spilling ever so slightly out from his jeans.
The dinner that night was polite. James made his way through rounds and rounds of drinks, ordering everything off the menu. Assuring me it was his treat. He spoke more about the footy, about the time him and his mates got “totalled” that one time. It began to just be sounds to me, I tucked into my food and let him blabber on. It’s a free meal, after all.
The bill came again and James took it off the waiter willingly. He smiled and began to shuffle through his pockets, rummaging through each one. Finally he paused.
‘Can I be cheeky?’ His hand was gently tapping the bill. ‘It looks like I’ve left my wallet at home, do you mind taking this one? The next one is sure on me’

I looked at him dumbfounded. Can I be cheeky? Did he think that would make this any better? I spluttered out a “sure” and got out my card. What was the other option?
We walked out, James’s arm trying to make his way down my waist. I pulled him away and politely farewelled him.
I drove home in a sort of confused rage, how did I let myself fall for that? Why did I just pay it so willingly?
I received one more text from him that night.
How many dates do we have to go on until we can become friends with benefits?
I’m committed, I’m smart, I’m the whole package. Everything you want. So how long?

I threw my phone onto the passenger seat of the car, revolted. Yuck, yuck, yuck. Which is when I felt it due course to consult some close friends. Show them what I was dealing with. My friend, Steve, would begin his rant about entitled bratty men and how they needed to be put in their place. The rest of my friends agreed. Astounded at my leniency, outraged that I would willingly let him get away with that.
Steve suggested a plan.
“Invite him over to yours this weekend, go out for dinner again and I’ll meet you. I wanna scope this guy out. Say you’ll shout him so you can get him over here and say he can come over.”
“I don’t really want him staying over the night.”
‘You don’t have to actually let him stay over. It’s just so he comes.”

So I set Steve’s bait. James sounded so obviously eager it was a little sad. We met in South Melbourne that night, close to mine. He had brought a dingy little backpack with him, probably filled with a change of clothes, condoms, lube, who knows. Maybe a wad of cash he’d swiped from an unsuspecting old lady.
The night went on and I remained flirtatious, polite, waiting on each moment for Steve to show up. James ran through drink after drink, his undeserved confidence reeked through the building.
Once Steve showed up though, the night only got worse. Steve saw through his shit immediately, unimpressed by his cockiness. Unimpressed by his pudgy belly and thinning hair. He ordered a couple of drinks on my bill and left, claiming he had other plans. James barely noticing Steve’s distaste.

As he left, my phone buzzed. DITCH HIM NOW. I locked the screen and continued to pretend to listen to James blabbering on. Another buzz. I MEAN IT. Ditch him and leave him with the bill.
I thought about it for some time, looking up and down at James as he downed another Peroni scoffed his face with a little more calamari and aranci balls.
“Well I think we should call it night, right?”
“Sure.” His greedy eyes now looking up and down at me. He called the waiter for the bill, who handed it over to him. He handed it to me and I smiled.

I played James’ part as convincing as he did, tapping my pockets, shuffling through my bag, acting as if I was sure I had brought it with me.
‘Sh*t I think I’ve left my wallet, do you mind paying for this?’ I said, watching James intently.
James’ smile dropped, he picked up the bill to look at. Even in the dim lights, I could see the colour drain from his face. The bill was nearly $250.

“I don’t have that much money on me. I can’t pay it.”
“Sure, I’ll just transfer you some money now…”
“Can’t you just get it?”
“I…no I can’t? I don’t have that much money (even though today was payday). How much do you have? I’ll transfer you the rest.”
“…I have $35.”

“…I just had to pay my lawyer today and I had all these bills due and I left my credit card at home. Most of my money is in cash which I left at home, my mortgage is due…”
“Right.” I had stopped listening after “$35”. I looked back at my phone, Steve’s messages floating across my eyes. “Look, I’ll just check my car for my wallet. I’ll be right back.” I stood up, James was just finishing the last bit of the Nutella pizza. I assured him that I will come back with the money.
I didn’t come back.

I wish I could’ve come back, but only to see the fear in his eyes when he realized I wasn’t coming back. I made sure to snap the bill before I left, though.

The Bill
The Bill

The thing is, it’s not even the fact that he did this, and that he clearly does this on the regular. It’s that he was barely a 5, and I can do so much better than a 5.

For all those girls letting some undeserving man screw you over. Let me tell you, nothing feels more satisfying than screwing them over right back. Teach those boys a lesson.