$10 worth of chocolate coins?
My dad and his buddy used to make dollar bets and compete for the most imaginative way to pay them off. Of course, 100 pennies are a lot easier to manage than 1000. The two I remember best (because they sat on a shelf in my dad’s den for years) are 100 pennies securely glued in neat rows to a sturdy piece of oaktag, and 100 pennies suspended in a bottle of clear Karo syrup. That one was like a toy–turning it this way and that, watching the pennies drift around . . . yeah, fun times when I was 8!
Would your friend appreciate a creative and humorous payoff, or is he all about the cash? Would he prefer to be amused or simply $10 richer? You don’t want to piss him off just to satisfy your itch for vengeance. (Or maybe you do–your call)
I love the casino chip idea.
Pay him in something like Zimbabwe dollars or some other hyperinflation currency.
Firstly, he’ll be getting something like 26000 Zimbabwe dollars, so theres the joy of him finding out what thats really worth.
Secondly, by the time he gets to the bank to cash it, it will be worth 5 cents.
Otara
I agree with the idea that you should just pay the ten bucks. You made the bet and lost. Deal with it.
But if you want to be difficult, one thousand money orders each in the amount of one penny, should be an exasperating means of payment. Of course, you’ll probably spend several thousand dollars buying that many money orders.
Oh
Well it depends on how far you want to go, but pay by multiple checks. Perhaps 100 checks for $0.10 each, or if you can print them, instead of filling them out by hand 1000 checks for $0.01 each.
Give him a gift certificate to some place he will never shop at, like Claire’s or Bath and Body Works or something.
Sorry, beautiful, he can just pawn that off on his girlfriend and lok…“thoughtful”. You know how that goes. This idea just won’t do (not at least for girly stores).
Huh, I guess I can post from my BlackBerry even if I didn’t think so.
What I meant to write before was to point out that this is some guy’s winning NCAA bracket, so the $10 the OP owes is just a share of a larger pot (10+ people every year). So yeah, the winner is really interested in the payola, but at the same time, if he’s getting all cocky and trash-talking, giving him one share of his take in some token annoying form is par for the course.
Paying him in pennies is overdone and pointless, and gluing pennies to 2x4s is going rather too far to be annoying – it’s so useless as to basically be reneging. Similarly, paying in some exotic casino token is not really paying off in legal tender. Pull this kind of stunt and it’s you who will not be invited to play in next year’s bracket instead of him.
I’d say, paying in Susan B’s, $2 bills or Eisenhower half dollars is about as far as you can legitimately go. That or paying with a really obnoxiously patterned personal check (e.g., if he’s a Yankees fan, paying with a commemorative 2004 Red Sox World Champions check pattern with the comment “Biggest Choke Job In Sports History XXXOOO” in the memo line).
Side note: if he’s clinched the bracket before even the final game this year even with the Final Four consisting of two #1s and two #2s, and the Elite Eight almost entirely of the #1/#2 teams paired (the exception being a #1/#3 seed pairing), I have to say he may indeed be good at picking the bracket compared to the dinguses he’s schnooking. runs
Pay him the money you owe him. A $10 bill.
Talk shit after you win one of these bets. Until then, he owns you.
Honorable, schmonorable. Fact is, we’re good friends, I don’t care much about ten dollars, and I am an immature, sore loser.
He doesn’t actually think he’s good at gambling, but he makes a distinction between filling out a bracket and shooting craps. Incidentally, he is a very good poker player.
I would give him a mix of foreign currency, but I think the only stuff I’ve got around here are a few loose Canadian dollars and Euros.
Okay, so make it dollars. Easy to set up, but a giant pain in the ass to find.
Put ten dollars worth of pennies in a big glass jar. Fill to top with water.
Put cardboard over jar, flip over and put on friend’s table. Very carefully remove cardboard.
$10.00 in coins, glued to…
-his front door.
-his driveway.
-the tires on his car.
-the inside of a wheelbarrow.
-a mobile.
-a hard-hat.
Alternately, I like the “assorted amounts hidden around the city and treasure map” idea.
Or, a way to man-up and admit defeat while still being a bit childish; Buy a glass piggy jar and have it etched with “YOU WIN!” (or other words to that effect) and fill it with the exact amount in coins.
Take a ten dollar bill, cut it in half.  Buy a greeting card. Write the following inside the card. “Dear ____ I lost the bet, unfortunately I am a little short on cash right now, and can only pay half of the bet.”
Enclose the half of the bill.

You. Are an Evil Genius.
There are a lot of Evil Genius Hopefuls in this thread, but you, m’dear, have achieved Evil Geniushood.
Well, I did some research and here are some 1¢ stamps the US Post Office is currently issuing:
This one honors the American Kestrel
and this one honors the Tiffany Lamp
Okay, stamps aren’t legal tender per se, but it seems a legitimate way to pay off your debt and still have some satisfaction of diminshing the value of his victory.  And it won’t backfire on you.  If he refuses the stamps, you can always use the darned things.
Those other ideas such as the casino chip, how are you going to get that? And if he refuses it, how are you going to transact that?
And I would also like to acknowledge Annie-Xmas’ “Evil Geniushood” status.
Wait until you know he has absolutely no cash on him and you are around a lot of friends. Give him a $20 dollar bill and tell him he now owes you $10. Pester him loudly and in front of friends about how he owes you $10. If they look curious tell them it’s from some sports bet and he still owes you $10. Interrupt him if he tries explaining it and instruct him “just answer the question yes or no, do you still owes me $10?”, “And yes or no, does this have to do with a sports bet?”.
Annie, that is brilliant. I’d have to give it a test run before trying it in his room, but I’ll have to look into it. The casino thing is a possibility. Detroit is close by and has a few casinos, and I don’t think he’s gonna be making it over there anytime soon without a car.
Thanks for all the kudos, but the idea hardly originates with me. It’s my favorite method of leaving a tip for a bad server–put five pennies in your water glass and flip it onto the table.
But I am an Evil Genius.