Sacrifice gambling to help a friend

I have a buddy who manages my money and is good at it.  Unfortunately, he's made really bad decisions when it comes to his own life.  He quit his job as a VP in an investment firm because of spite....5 years ago.  Since then, he's been in and out of crap jobs and does some consulting to make a few bucks.  I've helped him out more times than I can count.  Couple hundred here, couple hundred there.  I also pay him to manage my money. 

He's been to treatment twice (most recently got out about 2 months ago and has been doing better).  Of course, he had no car when he got out so I went around, looked at about 7 cheap ones, and bought him one for a grand....he only had $800 so there is $200 more I gave him. 

First thing I warn him about:  Do NOT drive in lousy weather until you get insurance (he was going to have to drive it for about a month before he could afford insurance).  First nasty storm we get he gets in an accident (his fault of course).  Luckily, the other person will let him work out a payment plan and didn't call the cops. 

Moral of the story:  Some people just never figure it out.  My friend now has a place to live (sober house) and got a job stocking at Target.  All he has left is the clothes on his back right now.  He's trying to start over.  I hope he makes it, but you just never know. 

I can't say don't give your friend the money, but you better be prepared to never see it again.  I've probably given my friend $2K or $3K over the last couple of years.  But I'm at the end of my rope and he knows it. 

Good luck.  It's really tough to say "no."  Been there.

I like the idea of a holiday parlay in his name leave it up to the gambling gods. If this is a very good friend then you really should help if you can if these conditions exist.

1. Your friend understands and appreciates that he is putting you in a bind with your wife.

2. That he is not just a lazy ass that lost his job for a reason(his fault) or is the type that will only take work that is of his status and feels the world is to blame.

3. That if he is unable to find a job after a set time then interest should build untill such a time as he can repay with NO LIMMIT on how long that is.

Good luck

By the way, I paid $650 so he could get his truck fixed.....only to have to junk it (which I knew was going to be the case as it really needed ).  And I also paid to have his cat euthanized.

You never know when the requests are going to stop or if you'll ever see your money again.  Just know that.

He's an alky. You'd be enabling him. It would actually hurt him more than help him. Blame it on your wife ...Because he won't understand the truth anyways... and you can keep his friendship if he ever cleans up. IMHO.  

I think you have the wrong idea of what an alky is. Every alky doesn't push a carriage around downtown. It seems to me that his life has become unmanagable.

k this is simple now.

you sound similar to me in this regard. youre a good person and will always be a good friend and have principles of your own. you will have issues mentally either way but you will regret not helping due to your nature more then saying no to him.

give your friend some cash now, see what happens in a few so you can keep your hobby afloat.  if youre willing to do 10, start with one mths worth of whats needed and then say the max you can do is helping for some of one more mth...

you should not have any remorse...

youre a good friend homey.....

just dont be a push over. trust me i know about putting others before myself.

I agree with the mention re. monthly expenses.  If he is really doing everything he can to cut those and is really working hard at finding a job, that makes it a little easier to consider.  My buddy was lazy...he had limited expenses....I told him to go get a job shlepping coffee or something like that.  ANYTHING to pay the bills.  He finally has. But it took a long time.

Another thing to consider:  If you loan him the money, will he suddenly lose his sense of urgency?

And the first thing I did when I got a "real" job was to put enough money in the bank where I could live easily for a year without unemployment or anything.  Lesson to all the folks out there early in their careers. 

If you do decide to lend him the money I'd get something in writing signed by him saying it was a loan and when it will be payed back. When you take him to small claims court Judge Judy will want to see documentation.

I would also ask the wifey if he agreed to sign a loan repayment document she might be ok with it.

It's a tough spot but I would only lend him what I could get back in small claims court. Sounds harsh but you have to cover your own ass. And if your friend doesn't want to sign that'll let you know how trust worthy he is.

Just my 2 cents. And best of luck.

....and some huh?.....uuhhhh...i may have done did change my mind on this one k.

this guy needs to understand priorities. downsize...

goodness this cat needs to get a cheap ass place to live, get rid of the ride, get a job, any job, that he could use BART to get to and stop hounding you. yea it sucks hearing a friend in need and in a rough spot, but f*ck this about you pissin your money away for his bullsh*t selfish reasoning to keep his life the same. sh*t, maybe he shud consider bankruptcy.

tell him in a nice way sh*t happens...deal with it. we all do...

he could be calling cc companies and getting a freeze on his accounts for 6 - 12 mths due to hardships without destroying credit.

for food tell him to extra value it for as long as it takes...2 meals a day...thats half the food costs at least.

and pcs metro time or any deal out there for the holidays for a 50 unlimited plan.

goodness does he want his weekly massage too...

not talkin sh*t about your friend but damn sh*t happens. we all deal with it. time will make it better the sooner he wakes up and eats some humble pie.

Kaufee, your loser friend wants $10,000 to get by?  He is living way above his means and thinks he is too good to work a couple of $10/hr jobs.  He should be thankful if you just stocked his refrigerator and pantry with enough food to last him a month. 

Also, hiding this from your wife could have an adverse affect on your marriage, as she will probably not trust you down the road.  If you want to cave in and enable him, let him live a month or 2 with you and the wife and that will almost save him 5K.  And you will not lose any money out of the deal, but he must have some job/jobs within the second month.

Tell him to rent in Oakland.

Then if he picks up an under the table job ... for 10 bucks an hour.

All set.

2500 in rent asking a buddy for 5,000