In response to: "What do you guys/gals do when family/friends ask for money?"
It depends.
Twice, I have helped family who fell on genuinely hard times. When my dad (Detroit auto worker) was unemployed for two full years, and unemployment ran out, I asked if I could pay his health care premium and utility bills. It was a bit more than $200 month but I knew it was temporary. I wanted to repay him for all the awful, factory overtime he put in to keep my brother and I out of Detroit public schools and in our Catholic one, and all that. I also figured, somewhat selfishly, that it was better to help him at the time than have him use savings that he needs for retirement, which I'd probably have to make up for down the road.
My brother was unemployed for a while at the same time, and I let him live for the price of utilities in a condo I owned in another state (with better job prospects) that wasn't rented, and was up for sale.
On the other hand, a very close friend of mine was recently unemployed. He was hinting around at needing money to see him through until his first pay day at a new job. His pay day was in a week, and he "only had $500" to last him a week until pay day.
He's single, has no children, and has two pets. He is also someone who, while unemployed, bought himself a brand new iPhone (mine is from 2009) and was worried about not being able to send the dog to day care (while he's unemployed and home all day!). In a laughing way, I said "We spend a lot less than $500/week between the two of us! What's the deal -- you got some debts or something you need to pay on?" (Hey, I've been there.)
"Oh no..." And he trailed off. And that time, I just couldn't bring myself to give him anything. I was kind about it, and we're still very close friends, but I said "Man, if you can't make it on $500/week, my giving you more money won't solve that problem." He said, "Yeah, I know, I know, but I'm not like you, I'm just not willing to do some of the things you do..." At least he owned it.
He and I are close, so I had some leeway to say certain, more forward things in a certain way than I might with other people, but I also felt like it was "a teachable moment."