Yeah I agree I guess. I have to admit I'm a bit surprised by all of this, because I always feel like he has held himself to a higher standard than to ask his friends to pay his credit cards while he travels to another continent to "find himself."

If his needs were more immediate and dire (need 20k for an operation, kid needs operation, etc), I'd be inclined to do it, but just to pay off credit card debt, elective shrink sessions, and a trip to uruguay.. I'm not sure it's appropriate for me to make this loan. I work my ass off at my job and have a family to support. He hasn't exactly killed himself working in life.

That said, this isn't some random guy. We're talking about a top 3 friend of mine for 27 years or so, and he's never asked me for a penny.

No way man. 34 year olds going to South America to aimlessly find themselves are losers. The fact he wants two of his better friends to bankroll it is just...wow.



Let me ask you something: At this point in your life, is this a guy you like to hang around with? Do you even hang out with him now, or is he a friend from your youth?

Tell him he can take the money, but he has to understand that it'll cut you two off entirely. It's finished. Over.

Then even if he says "okay" you can be like "Eff that, you're a horrible friend."

Talk with him. See if something like this works out.

You and friend give him the $$ for the CC bills. Tell him to get a job here, start saving, then talk about the rest of hte money.

I think if he just asked for the money for the CC bills this is a complete no brainer if this friend is how you describe him to you. The additional for the sabbatical is absurd.

I see him about once a year. We live in totally different parts of the country. We email maybe 1-2 times a week and talk on the phone maybe 2-3 times a month.

He was in my wedding party. He has always been unselfish with me and is an extremely kind and understanding person. He would never backstab me in any way.

No, because the email begins with, "Let me start by saying that I expect nothing from you. Please feel no pressure. I only went to you first because I consider you my best friend. I know you have a ton of responsibilities in your life, and this will only work if you won't miss the money for 2-3 years. I will pay you back slowly over this time period...'

You have a pretty warped view of male friendship if you thinking shipping $20k to a top 3 friend for something nonessential is standard.

You need to read this sentence a few more times.




Speaking personally, and I'm one of the most loyal friends going, I would seriously, seriously rethink this relationship after this ****.



GEORGE IS GETTING ANGRY!!!...

I think you were intentionally trying to make the point that this sizable request was made via email. Regardless, this resonated for me.

I have a best friend. He has a wife and two kids and is the gentlest soul imaginable. At one point when he was going through a rough time I thought he was going to ask me for money, but he didn't (I offered, he declined). Anyway, this money wouldn't have been to go to Rio, it would've been to pay for food and mortgage and clothes. So a little different, but still: never in a million years would he have shot me off an email asking for dough. I mean, come on. A couple of clicks? Call me old-fashioned, but this is a conversation that needs to be had face-to-face, or AT LEAST on the phone. But the email nature just pisses me off (again, I'm old, but not much older than OP).

So, no. I don't give someone who can't ask me to my face, or at least to my ear, the money.

Cant he try to get a job inside of the US wouldnt that pay better?

There is no way out of this, imo. You and he are no longer friends, whatever you do.

It sounds like your friend is not well grounded in reality. His requests are unreasonable and unfailr.

If he has 12k in credit card debt and no income, he can easily declare bankruptcy. His credit will be **** for 7 years but it's probably not all that great anyway. Some people may think it's the easy way out or isn't the 'right' thing to do; I agree to some extent, but it's still better than shifting the debt to his friends.

5k to go to South America to explore career oppurtunities is far from a reaonable request when there are jobs which can be had in the U.S.

The only thing I would consider helping out with is his therapy bills, that sounds like a real need for him.

Helping out a friend in desperate straights with legitimate needs is fine. Enabling him to trapse off to South America while you pay off his debt doesn't qualify for that.

20k is way too much for something like this unless you're a baller. The chance of seeing this money back is pretty slim in the not distant future. I don't have a lot of sympathy for credit card problems.

This sucks. It's a total catch-22 situation for me.

Tough spot, but the answer is still no.



Now let's talk about the wife for a second. Why would you even consider this if the wife is so dead set against it?

You have a couple rainy days and that **** can break up a marriage, for reals.

It would only be $10k, which is still a lot. I have a high income but I have major expenses. So in terms of what I have left every year at the end of the year, I'm not really a baller.

I.E., I care about $10k. It's not just lint in my pocket. I can easily afford it, but it's not like it means nothing to me.

Her viewpoint factors way in, but at the end of the day I'm not going to be dominated by my wife on every decision I make, and the same goes for her. That's not a way we like to live. He's my friend, and we (my wife and I) both make our own money.

How is that?

Your wife hates the idea and zero people in this thread have said yes, you should give him the money.

The answer is crystal clear.

You prefer being bent over by your male friends?

Do not lend him that much money. How about you and your friends chipping in to purchasing his plane ticket as a gift?

I also think it's insane to loan money to someone who:

- has proven irresponsible and has no wife, kids, or any other responsibility save for a crumbling family
- a pile of debt from American companies that's easy avoided from another continent
- is going through a what-does-it-all-mean crisis
- intends to go to the land of cheap and available drugs
- likes to powder his nose

This really is like giving whiskey and car keys to your teenage son.

Wow, I didn't realize he did this in email. IMO more therapy and less travel. (Obv not $3K kind of therapy).

Just tell him you'd love to help him out but there's no way you can afford to part with $10K.

Tweety, your wife is your partner and it doesn't sound like she's being dominating or unreasonable.
If it's none of her business, she probably should have been spared the details.

What are your wife's thoughts on this guy? You must have discussed him once or twice.

it's a catch-22 in that we are all playing the role of his wife here - we see no tangible benefit to bailing the guy out, but tweety very well might. the guy has gone through some hard times it sounds like, however many of them were self-created.

but yeah like LFS i think sending an email asking for money is fairly low - although going through the rigmarole of catching up with a friend only to have him hit you up with a money request is going to come off pretty low too.

missed the blow reference in the OP,


just get him an 8-ball and cut him loose