I agree with all of this. I would add that the benefit of all of this is some interest money saved. It's not like they're going to take his house or something. So basically we have little benefit and a high likelihood a really bad outcome - losing the 10K plus having the guy **** his life up even worse with that money or because OP gave it to him.

On top of all this OP's wife completely reasonably is opposed to the whole thing. This is a massive no-brainer.

Tell the friend the truth. If that makes you cold that makes you cold.

Semi-grunching but I have experience on this issue and know of what I speak. You can't loan him money. You might give him money, but it isn't a loan. Banks and the mafia can do loans because they are prepared to go through the unpleasant process of collections. Are you?

You'll sleep better, and have a better chance of still being friends with this guy long term (as opposed to hating him for life), if you give him as large a gift as you're comfortable making. That is, if you think he deserves it. And it is 100% a gift. You won't ever have to call him up and ask "where's my money". Because it won't be your money anymore. Finally the most important step: never think about that money again.

I should add, make it absolutely clear that he can't ever come to you for money again. This is the last time. Select the amount accordingly.

Tweety

How about a comprimise. You and your friend lend him $3500 each. (7K). He can use the $5000 to get to South America and get set-up, and he can use the 2K to start servicing the 15K in loans he has until he can start making some dollars to pay them down and then off.

Suggest he should pay his loans down and off in the first two years, and pay each of you back in the 3rd year.

I would still approach this as if my $3,500 was never going to be seen again, but he truly means that much as a friend, I'm not sure why this would not work for him. If he hesitates at all, I wouldn't give him anything.

PS. call me a dic*, but I'm also calling the "other" friend to see exactly what his email said. I mean what did he say to the other friend....."I'm writing you second because you are my second best friend." I'd really want to know how up front this guy is. If he is pitching you both with "best friend" line, it is clearly a guilt pressure play.

If he wrote your friend a different note, appealing for money and speaking of his long-standing friendship (but not saying he was his best friend) than I would be inclined to find his request more sincere.

Best of luck.

BTW, I don't have any friends that would'nt want to work their butt off first and clear their debt before they ventured off somewhere. My friends would rent a room with a hotplate and work extra hours at a crappy job before asking for "find themselves" help. Now familily, that is another story.....lol

Great points EvilSteve. I still think there is merit in having two versions of this. One, your friend believes it be a loan, and knows that you expect the money back. Two, you have mentally written off the money, expecting to never see it back.

I could live with not getting the money back, but I would NEVER want him to forget that he welched out on me.

Knish: What do you need, 500? A grand?
Mike: I need 15,000
Knish: 15?
Mike: Yep.
Knish: I need a blowjob from Christy Turlington. Get the f*ck outta here, $15,000?
Mike: Seriously, Joey... what can you do for me? $500 is not even gonna get me started.
Knish: Goddammit Mike, if 500 won't help, what's 2 grand gonna do?
...
Mike: I know I f*cked up. What I need from you is money... I need whatever money you can give me.
Knish: See that's the thing.. this time there is no money. I give you 2 grand, what's that buy you? A day? No, I give it to you, I'm wasting it.
Mike: That's f*cking great.
Knish: You did it to yourself.

damn it if roundersquote had just said 'you did it to yourself'...

I think loaning him part of it ($3500 or whatever) is silly too. You tell the friend that you are sorry but you aren't comfortable doing that.

He's super far away and you don't even know how into the coke he is these days, etc etc. You might only be funding his drug habit for a few weeks for all you know. But even if you weren't it shouldn't be that hard for him to save up and go to South America himself and get a job down there if he wanted to do that.

He has large CC debt but has been making very little effort to pay it off. He could have gotten a job before but instead is selling his shoes on e-bay and partying with the chicks and blow. Responsible he is not.

If he had an actual plan to get a job and be more practical about this and needed the money to pay off the CC before the rates went up and you could see it as being realistic that you would get the money back within the next 6-12 months or so BECAUSE he is showing you a real plan and not just wants to party and maybe...eventually...he'll get a job...well, then I could see loaning him $3k or even a little more to help him get back on his feet.

But he's really off-track and it sounds like his intentions are to stay off-track. And even when he says he has intentions of getting PART of his act together (did blow for the last time) he doesn't do that anyway.

It's not cruel to say you aren't going to loan the guy $10k. There is no Catch 22. You just say you don't think it's a good idea for you to loan the guy that much money that you aren't sure you are going to get back anytime in the near future. You can't afford to part with it. You can even toss in that it's because you have a wife and a kid (even though I don't think you should if you were a bachelor). Tell him that the wife won't let you if you want (yes, it's a lie...but if it makes you feel less guilty to put it on her then no biggie. He'll suspect it's you saying no anyway).

Lets be honest here. He's not paying you back after 3 yrs either unless he wins the lottery or something. This is GIVING him money that you should be using for your kid's college education or your own retirement plans or at least a new car, etc etc. You just tell him that you're really sorry but you aren't comfortable with it. That doesn't make you any less of a friend. However, he IS less of a friend and a person for doing that to you I think.

I don't think it has to mean the friendship is over though. If he's cool and doesn't completely suck then he should be totally understanding about it. He should already know he was out of line in the first place just to ask but evidently he doesn't quite get it. But if he comes to the correct realization late or is merely understanding of you declining him then that's fine too and you guys can still be buds and this little incident could all blow over after 3-5 years from now (assuming he doesn't completely throw his life away which it sounds like he's in the process of doing).

I disagree with most of the people in this thread.

I don't "value" money as much as health, family, friendship, etc.

If this guy is one of my friends of 27 years, I'm planning on having this guy around until one of us dies. If I was making decent money, 10k? No problem. Obviously don't expect it back, give him what you can afford, all that jazz, but how can you not assume the best, and that 3 years from now you'll be mostly paid back, and you will have really helped him out in a rough time. If he spends it all on hookers that's your bad for thinking he was a friend.

When your 2 year old gets married, who do you want there to celebrate with? If this guy has totally lucked out in maintaining a 27 year friendship, and might do some **** like this again, fine, listen to the people in this thread. But if you guys have been through some stuff before, and you obviously call this ****** and have a heart-to-heart about it, and you realize how damn hard it was to ask for money (we're not all Braveheart, he could have emailed cause he didn't want to cry over the phone) then give your best friend some cash. Be honest about now wanting to enable random, nomadic and lazy behavior, and that you will be hurt if it leads to that.

I bet you would lend him a car, or furnature, or some other **** worth 10k.

This guy is selling his sneakers on eBay for crying out loud!

Also, I can get how something really crazy like this can screw up a lot of your life but it seems to me that if he wanted to keep his work-life together he probably could have or if he wanted to put together a new work-life he could do that too. Same goes for the relationship bit as well. If he wanted to save the relationship I'm thinking he possibly could have. He didn't want to. And the convenient excuse why it fell apart for him is that his Dad went nuts.

I'm not there though and know nothing about his relationship or his Dad's situation. But it just seems too convenient to write it off that simply.

milliondollaz - Somewhat would depend on my own financial situation. If I had a million+ bucks and felt financially set then I would probably do it. But OP says the money is a significant amount for him even though he could survive to part with it.

My lower threshold would be if I had ~30k in a liquid account, and was making 1k more per month than I was spending. And 20k could hold me for a couple months. So if something happened to my life, I could hamper down and be back to where I was in about a year. $1,000,000+ is a no-brainer.

also

I agreed with a lot of what you said, but I strongly disagree here. If I were the one asking for money, and my friend said "dude, i'm not giving your ass any money! i'm afraid it will enable the lifestyle that got you into cc debt and sneaker selling", I'd consider him a way better friend than one who told me his wife wouldn't let him. If you're not going to give your friend money, at the very least give him honesty!

Tweety,

You are uncomfortable because your friend put you in an uncomfortable situation. He is leveraging your friendship to use to get free money. Everyone saying you will never get paid back is 100% correct.

You can go the EvilSteve route and give him a GIFT if you choose to do so. But here's the key. Make it an amount that you would be comfortable giving if the friendship were over tomorrow.

I think you are viewing "loyalty" in skewed terms. Just because you have known him for 27 years does not make him someone to toss 10k at. I think this guy is no longer a good friend and THAT is what's making you truly uncomfortable. A good friend wouldn't ask for 10k in email that is going toward subsiding the poor financial decisions (NOT an emergency) that he'd made over the last 10+ years.

million - About the 'wife won't let me' excuse I've considered that angle too. Personally I would go with the "I'm uncomfortable doing that. Sorry, just can't do it" route and would take all responsibility for it.

Just providing OP some ideas because it seems like even saying something like that feels like some sort of big portrayal for him. Plus, he is correct that if it's their combined money and his wife is opposed to it then her feelings should be part of the equation so it's not a total lie. I definitely think he should take the full thing onto himself though but was just offering another idea if doing that was REALLY that much of a problem for him which it seems to be.

i sympathize with your friend.. committing a family member to a mental hospital is among the worst things that a person can ever have to go through. t

hat being said, lending money isn't the thing that would help your friend the most. helping him find a job, manage his finances, declaring bankruptcy, etc are all better long term solutions.

A 27 year-long friendship is nothing to sneeze at. It's a $10k gamble I'd be willing to take a chance at and hope that this life-long friend figures things out quickly and get his act together afterward. Your friend is grown-ass man. There's no need to hold his hand and teach him to walk again.

Any money you would send him would be a waste at this point unless he plans to make some major life changes.

You have a family to take care of first and foremost, which it seems would be hurt by this if this is not an insignificant amount of money for you.

Reading some of the other responses, the point about making it a gift not a loan, is really a secondary point. Definitely don't loan him money, but with as irresponsible as he has been, giving him money may just add fuel to the fire and you wouldn't be helping him at all. If you knew the money would go directly to paying off his credit card, and that he'd stop using credit irresponsibly in the future, then you could feel good about that. Unfortunately it seems the money has a high likelihood of financing a continuation of the poor decisions that got him to the point he's at now. So like gtmwarrior said, maybe you can try to help him but without giving him money (since he's terrible with money).

I've had some long-time friends and know what that's like. The answer would still be no and I would expect them to still be my friend but if that didn't happen then I don't think that's my fault.

And this guy obviously is having a tough time handling himself in any kind of responsible manner at all so I think it's kind of obvious that he perhaps does need someone to just stop him and perhaps guide him some. He promises to stop doing blow and then does it again. He doesn't even bother going out and getting a job when his money is running shorter and shorter and he's selling his shoes (and blabbing about it to his buddies).

The OP needs to wake him up if he's a true friend and tell him what's what...mostly thinking of that big about how early he gets up and how hard he works to provide for himself and his family. Essentially his friend is asking that this guy should keep getting up at 5:30am and working as hard as he does to provide for him too. It's not like this guy accidentally gets up everyday and goes out and makes money. It's a decision to not be a total f-up. But this guy doing the coke and the partying and not having the time to get a job thinks that maybe his buddy can help provide for him to because after all, he's got some extra dough that he can spare.

The guy went out and got the dough himself and worked hard for it. It's not like it just landed on his doorstep.

Sometimes the most important thing a friend or family member can do for you is say no.

This is one of those circumstances. You don't say no because it's about never getting repaid or possibly ruining a friendship; you say no because it's the best thing you can do for your friend.

It's usually only people who really care about you that give you a swift kick in the ass when you need or deserve it.

OP, here's another idea. Take that $10K you were considering blowing on your friend and put it in a reasonable investment vehicle. Through the miracle of compound growth, that could put your kid through his or her first year of college.

Bankruptcy and give him his plane ticket as a gift. this is not even close IMO

But are you anyone's top 3 friend?

Pretty much everything has been covered extensively, but the one point that was lightly touched on that resonates the most with me is that this loan would do nothing more than enable his lifetime of degeneracy.

I wonder in what context the whole "I'm selling shoes on Ebay" came up? Was it in the e-mail asking for the "loan" or in some recent conversation? If it was in the e-mail then he's playing at your emotions, and if so that plus his gameplan to leave the country to "find himself" proves that he is woefully out of touch with reality or at least willfully avoiding it.

No matter how bad the economy at the moment, if he is literate and presentable there is always a job for him if he looks for it doing something. That he evidently isn't trying very hard should be a concern to you. What are the odds he goes to South America and randomly grows a work ethic? Pretty slim to none, it's much more likely he'd chew coca leaves all day and fall in with some liberation army in Chile.

Also the long nights of doing blow would concern me if I were you. You only see him once per year, how do you know he doesn't have a problem with this? He may not but damn, the dude is in his mid-30s and partying like it's ten years ago. Gotta grow out of that sometime.

Final point: some posters have said he can "go to South America and make money there to send back to you". That is exactly backwards. He'd make a fraction there of what he could make here doing the same thing. Mexicans and Indians come here to make money and send back to their country and family; Americans don't go to Bolivia to support their family here unless it is a highly specialized skill and it pays American dolares.

Bottom line, you sound like a loyal friend and he sounds like he's in a bad spot, but you'd only be helping him escape the reality he needs to face eventually.

I can't imagine the doing a bunch of blow has helped with his mental health or his work situation. He'll attribute it to other things that are "out of his control." He's irresponsible. Clearing the slate for him isn't going to magically give him the ability to be responsible.

Giving him money won't help him improve his life. It'll just tide him over for a little while until he's back in the same spot. At that time he'll ask you for some more money. Don't enable his lifestyle.

DO NOT GIVE HIM ANY MONEY!

What is the other friend's reply?

email? really?

and wtf at specifically South America - even deadbeat college grads can go teach English in various random Asian countries for zero money up front + they often pay travel. in fact, some of those places *do* let you save up 15K over a year or two if you're cheap.

send him a link to JET, problem solved?