Should I lend him money?

NO. I understand your desire to help out a friend and someone you think you can trust. BUT the big rule about lending money is this: No loans to family, friends, or cowokers. This sort of thing almost NEVER ends well, and "tough love" (meaning saying no) in this case will be a much kinder thing long term (meaning you can still work together and be friends). On top of that you will not get sucked into his vortex of debt/ possibly irresponsible choices (since I do not know if his debt is due to a vacation or big old flat screen TV, girlfriend/lifestyle he could or can not afford vs. healthcare for his ill child, I am not judging here).

What you can do is help him look online about credit card debt, smart negotiating with credit card companies, and then refer him to some local, free debt and money management lectures in the area. We have a free class about finances every other month in my area sponsored by our library and run by retired accountants, professional investors, etc. through continuing adult education in our area where you can get excellent free advice. He needs to learn this lesson himself, and not include any one else in the big mess he finds himself in.

If you have an issue just saying the words NO for some reason you can soften it with something like,"I would love to be in a position that I could help you out, but I am working on securing my own finances at this time. I am trying to build my three month expense emergency fund, and have to get the last of my retirement funding paid so I can take advantage of this tax year. (or whatever your situation is) I have heard that there might be free financial lectures or advice locally and online that might be really useful in dealing with credit card companies, perhaps you could look into that."

p.s. Sorry for another edit, but what I do not "get" about this is that almost ANY bank would be happy with those terms to have that amount paid off if he would call and negotiate terms. I am sorry, I know you like and trust this person, but I sense something is just not right with this!! So my advice? Say NO!!! for all you know, you may be paying for someone's coke or gambling habit, and although you know this person and do not believe they would be doing anything like that the truth is, we REALLY never really know someone 100%. Be careful, that is quite a chunk of change to never see again/pay for a life lesson!

i'm too undesirable to lend human beings money, so genuinely I hate it whilst human beings ask. As a conventional rule, i don't lend money except i'm arranged to settle for that i wouldn't get it decrease back. Lending money can carry approximately lots drama, resentment, broken relationships ect. A twelve months in the past, I went to flow meet a buddy (for the 1st time) in yet another state. we live very a procedures aside, so met in a state interior the middle. I had offered a plane cost ticket and each thing. a week before the trip, he tells me he isn't gonna be waiting to pay for his a million/2 of the hotel, yet that he might desire to pay me decrease back a week or so after the trip. I had no decision yet to assert confident (i could not refund the plane cost ticket). in any case, so he's by no ability paid me decrease back the $a hundred he owes me. And he lives a procedures away, so that is in contrast to i will in basic terms flow and demand it. i'm nonetheless bitter approximately it nevertheless. He makes extra $ than i do and has way much less costs, and that i'm a suffering single mom. there have been many cases as quickly as I desperately might have used that $a hundred. So i for my section attempt to sidestep lending human beings money.

If you have to ask "Should I lend him money?" the answer is always a definite NO, no matter what the details are.

And having read your details, the answer in this case is a definite NO. He has proven by his actions that he is a very bad money manager. If he can't come up with the money to pay his credit card bill while making what is a VERY decent salary, he's certainly not going to be able to come up with the money to pay you back. I'm guessing that if he paid off his credit card, he'd immediately start using it again, and within a few months would owe both you and the credit card company.

Unless he's going to pay you back all the money in 2 or at the most 4 lump sums I wouldn't do it. Why would he rather pay you 20% interest when he could get a lower rate from his bank?

A bank would be taking some kind of collateral. and their paperwork has been drafted by a team of lawyers.

What kind of collateral could you take? Can he put his car in your name until he pays it back, his mothers jewellery? He should trust you as much as you trust him right?

Bad idea. Very bad idea. If he was financially irresponsible to end up where he can't pay his own credit card bill, what makes you think he's suddenly going to be more financially responsible to pay back you (and the bank loan, and the credit card bills because let's face it - he will continue to spend himself into a mess).

You are not a bank.

Ask yourself. Why isn't the bank lending himi/her money?

Because the person has bad credit and a history of not paying back loans.

If you do this. Never epect your money back. You will not get it.

Then, you will sue him in court, and win, but probably still not get your money.

Friends/coworkers and money never mix. It causes problems more times than not. It's not worth it.