Sacrifice gambling to help a friend

I could see if he had kids and his wife died from cancer or something ...

any single man should be able to take care of himself.

Don't do it. This guy needs some tough love ... not 5k handed to him.  

https://sfbay.craigslist.org/sfc/apa/2755325087.html

595 per month sounds about right for him.

Quote Originally Posted by Kaufee:

I know he's been looking hard for work. But, you guys might be right. He may have to lower his standards on what's an acceptable job. He was making somewhere between 80-100K at his last gig. He's prob searching for work in that range and is likely looking right past any jobs paying significantly less. It's not that he thinks he's too good to take a lower paying job. I just think he's become accustomed to a certain way of life..

You guys are starting to make me realize that's what needs to change 

There is NO shame in him working a couple of menial jobs to get back on his feet.  Your friend is DELUSIONAL, and NO good will come out of handing him charity.  As some other posters have wisely stated, help him move or find him work.  Anything above that is unacceptable and insane on your part. 

Kaufee, do not feel guilty because you are smart and have your life in order.  He will only drag you and your wife down if you throw money at him.    

 Keep us updated.

Sounds to me like you're not exactly "rich" but def not poor.

It also sounds like you have one nice little 10k secret nest egg that you've kept hidden away from your wife that would be available if you truly need it.

At any given moment something serious could happen in your life, to your health, to one of your family members, etc. At the drop of a hat YOU might need that 10k for something. Impossible to foresee now, but the second you loan that money you no longer have it, and you just never know when something might happen in YOUR OWN life where that money might save a situation.

Let him man up. He will figure it out. You know damn well you're doing nothing but bailing him out, you're a good friend because you've clearly put his reality on your conscience but it simply isn't your problem. Obviously he has some capability if he can generate good money when working, so let him draw on that brain power and he will figure this out on his own. Trust me, he will figure something out, with or without you.