Yeah, I mostly spelled cheques like that just to piss off my American readers. Canadians are strange! We spell words differently!

Every group of friends has one of the following people- the OCD person who insists everything is done equally. Rather than throwing in his $20 towards the group tab, he’ll examine the receipt with the zeal of an unemployed writer heading to Starbucks. Since he only had the cheap meal washed down with delicious free water, he only owes $7.95. Since he’s not a cheap guy and he tips really well, he insists on leaving his $2 tip, a cool 25% of the bill. He thinks he’s being generous because it’s such a large percentage, without realizing it’s just a lousy 2 bucks.

As an aside, I still don’t get why frugal people tip so much.

If you’re anything like me, you don’t like these people. I understand being frugal and smart with your money, but these people take it too far. Every group of friends has one, mine included. And no, it wasn’t me.

And yet, even though I was cemented in my ways, I came to realize that these people aren’t so crazy after all. I had an epiphany.

Without getting into details, a friend owes me some money. We went somewhere together, and I footed the bill, with the understanding I’d be paid back. A few days passed, then came a promise that I’d get paid next payday. That day passed and no cash. Another few days went by, with another failed promise to pay. It’s gotten to the point where actual dates have been replaced by vague promises.

Now, I’m not terribly concerned about getting my cash. I know my friend is a stand up individual who’ll settle their debt. I know that I’ll get paid eventually. I have absolutely no problem harassing my friend over and over again until the debt is repaid. Even though I’m certain there’ll be a positive outcome to this, I’m still pissed off, for three reasons.

1. My friend is enjoying the use of my capital, interest free, with no rush to pay it back. As a capitalist, this makes me mad. I’m actually contemplating figuring out how to get him to buy me a blizzard in exchange for this interest free loan. I can’t get too mad about the ice cream level if I don’t pay for the blizzard.

2. My friend isn’t a poor guy. He makes a decent living, he’s just no good at managing his money. If this person really wanted to settle up, I’d have been paid back weeks ago. He’s in no hurry because he has more pressing creditors. I can wait, he’s just passing time until I start insisting on the cash. Essentially, this person is using our friendship against me. Well played sir.

3. It’s the principle of the whole matter. If you owe somebody money, you should pay them. That’s what trustworthy people do. By even delaying payment, you’re taking advantage of somebody’s good nature.

So what’s a fella to do? Well, there’s two things I’m taking away from this whole experience.

Firstly, never lend money to your friends. This can only end badly. Unless your friend pays you back in full right away, you’re going to be mad at this person. This much is obvious. This brings us to point two.

Insist on separate cheques.

I don’t care where you go, insist on separate cheques. Don’t do the I pay for this one you pay for the next one thing. Don’t buy supper if he’s going to buy hockey tickets later. Tit for tat will not work. At some point, one of the friends will get a little too comfortable with the arrangement and will only offer to pay when the tab is low.

And to further complicate the rules, all the rules go out the window when you’re dating the girl. You will pay more often than she does. Because she will repay you in other ways.

Once you decide to be the guy who always asks for his cheque separate, you will be made fun of for being a cheap bastard. It won’t happen to your face, but it will happen behind your back. Which is why you shouldn’t do this all the time. If you’re hanging out with a new group, just throw in your $20, even if your share of the bill only comes to $14. Since those outings only happen a few times a year anyway, no sense getting your panties in a knot about them.

Chances are, you’ll have about 5 people you regularly split stuff with. Just insist on separate bills and make your life easier. Oh, and never, ever, front the cost of an event with the expectation of being paid back after. That’s the point of this post, but you guys deserve more than a one sentence post. Well, some of you do.

Tell everyone, yo!