Several years back we bought a nice sleeper sofa and matching chair from Montgomery Ward’s. It was a clearance sale while they were going out of business.
When they came to deliver it, they couldn’t fit it through our door, so they took it back.
$900.
Never got our money back.
My security deposit from my last apartment, because my landlord’s recordkeeping system sucks.
$2.50 I lent to Jane.
How far did you go to try to get your money back?
Faxing receipts, phone calls, etc. It was my husband’s debit card that it was on, so he had to be the one to deal with it, and he didn’t do a very good job. I was actually quite pissed off at him for quite a while over it.
I don’t remember that. Do you want me to mail you a check?
I hope to go out in a splendid blaze of glory long before I reap the benefits of my 401k.
That five pound note I found down the side of the sofa yesterday. My SO took it! Evil money-grubbing bastard. He had some kind of penile/bovine story about having lent me twenty quid a couple of weeks before, but I don’t believe a word of it. Upholstery treasure is finders keepers. 
Arrgh. “Lost” money is one of my pet peeves.
For example, my SO’s little brother still owes me $350 from the time that we lived together (as roommates). I’ll never see that money again.
Or, it could be the $500 that I gave a friend because I thought I was purchasing his laptop. Turns out his dad is going to need the laptop afterall, so I’m not going to get it. And I have no receipts. (He still brings it up to this day that he knows he owes me the money, but I’ll never see it, regardless of the fact that he just got a promotion and a 10K raise.)
My former roommate owes me about $2500. I consider it gone, never mind that he has a great consulting job now and had money coming out of his ears.
It’s just gone. And I’m wiser.
The $500 my old girlfriend owes me. She also still has my VCR.
Actually, I consider $500 + 1 VCR a fair price to get her out of my life.
Oh, and about 99% of the money I’m paying for Social Security benefits. By the time I am old enough to collect, the retirement age will probably be 80.
I don’t know if this counts (since I consented to the robbery)…
Last August, I arranged (via the internet) to buy a car from a guy in Michigan (I’m in Kansas).
Absolutely stunning automobile. 1973 Lincoln Mark IV, pristine condition, black with a white leather interior. Amazing.
Anyway, I was scheduled to fly to Michigan to pick the car up on September 13 of last year. I guess you can figure out that THAT didn’t happen…
…however, the WTC tragedy not only prevented me from flying to Michigan on Sept. 13, it also forced me to rearrange my priorities a little, and I started feeling like a spoiled, impractical princess for buying this car (the reasons are too many to list, but truth be told, I couldn’t afford the price or the upkeep of such a car, anyway). Actually, I felt that way even before Sept. 11… I just didn’t feel guilty about being spoiled and impractical until this point.
So I backed out of the deal. The guy was AMAZINGLY nice about it, so I offered to let him keep a portion of the $1000 deposit I’d already sent to him, for his trouble. I’m not a believer in making offers I don’t plan to make good on, but I think maybe I was expecting him to say “Nahhh… that’s OK” (especially in light of the fact that he’d promised a full refund of my deposit if, after seeing and test driving the car, I wanted out of the deal).
He kept $250.
So basically I paid $250 to email this guy for a couple of weeks, and look at pictures of a beautiful car.
But I don’t blame the car guy, really; I blame the friend who talked me into getting the car in the first place. I mean, it’s true that I hate new cars (and that I thought this one was absolutely gorgeous), but left to my own devices I never would have:
a) actually tried to buy a car (via the internet, sight unseen) from another state
b) opted to pay that much money for a car that old (given my current financial state), when the same amount would have gotten me a nice, reliable newer Honda or
c) thought it was a good idea to buy a classic car in pristine condition for everyday driving (which involves trips to the grocery store–where errant carts run amok in the parking lot–and hauling of dogs and dirt).
However, my friend talked me into emailing the guy “just to see”, and then kept on enabling me until I’d sent that $1000 money order.
Now I’m out $250 for nothin’, all because of my friend.
Whaaaat, am I supposed to blame myself, here??
As it is, I wound up with a charming, reliable, and comfortably crusty old BMW that gets great gas mileage and was well within my price range.
But I still miss that $250.
I once lent a friend $1000 to pay his college tuition. He gave me a series of post-dated checks to pay it off, with interest, with the understanding that I wouldn’t cash 'em without checking with him first. This worked for maybe 1/4 of the payment. Several years later, he got married. As a wedding gift, I gave him the remainder of the checks, torn in half - I basically forgave his debt to me. Essentially it was a $750 wedding gift. I also gave him and his wife a really nice bottle of wine.
He barely said Thank You. He didn’t say “wow, what an amazing gift!” or “you’re too generous!” He sort of mumbled ‘thanks’.
Fucker. I’ve barely talked to him since, and that was 4 years ago.
I happened to be the person going to the shop last week and bought 4 bottles of wine for myself and my friends. They said they would give me the money later but they haven’t mentioned it and I know I will never see that money again 
At least I didn’t buy decent wine
Ex’s car died. Lent a grand towards replacement. I’d be more apt to believe someone who says “Trust me, I’m with the government” than I am to believe her “I’ll pay you back when I get the money.” I considered it just more unofficial child support.
I also lent a friend money.
We went shopping for some jeans. I bought a pair and so did she, except she didn’t have enough money to pay for them - so I loaned her $169. I managed to get $49 of it back by getting her to pay for something that I would have bought, but that’s been it so far. She’s put off paying the rest back for about 7 months - half the time she’s spent whining about how she doesn’t have enough money and the other half has been spent clothes shopping. :rolleyes:
And then stupid, stupid, STUPID me lent her some more money. She had bid on an American seller’s auction and was too cheap to buy a money order, so asked me whether I could pay her with my PayPal account (dad’s credit card). She told me that the seller was on the verge of giving her negative feedback, so I paid for her. I’m paying my dad back out of my own money, so if she doesn’t come through, I’m out another $50 or so. (Okay, so this one was really my fault)
At least I wised up when she wanted to use my father’s credit card to pay for her eBay account. I don’t think so bitch.
sigh I’m a little bitter today.
I’m probably out 3K just from covering rent for an old girlfriend and from subletters that never reimbursed me.
I’d hate to think of the number of tabs I picked up when friends were jobless, but that’s okay really.
My wife just inherited a real chunk of change though that we’ll never see because the benefactor’s goddaughter has already plundered her account. Now I hope ghosts are real.
Maybe I’m getting too old, but $169 for a pair of jeans? 
For my money, I lent 2 friends a total of $5000 in 1995 (3K to one, 2K to the other) and have been paid back about $500. I wrote it off a long time ago.
It’s amazing, isn’t it?
I’d be mortified to remember I owed anybody as little as $5 but to some folks it just really doesn’t seem to matter. Sure, when somebody’s going through a difficult time they should be allowed to delay repayment but when they get back on their feet and conveniently forget? Well, that’s just crap.
xizor, it is Australian dollars, so it’s not that bad. More like $100 US.