As the U.S. economy enters its fourth year of turmoil, average folks continue to struggle. At GRS, we’ve shared questions and stories about people who can’t make ends meet, who are losing their homes, and who find themselves out of work. But we’ve never tackled the homeless before.

Today, though, Evan wrote with a tough situation. One of his friends is out on the street, and he feels guilty because of it. Should he help? What’s his responsibility here — financially and otherwise? Here’s Evan’s question:

I’ve read your website for years, but I ‘ve never written for advice until today. Now I could use advice from you and your readers.

I have a childhood friend who’s in trouble. I’ve known him since we were both ten. We went to school together, so I saw first-hand his rocky childhood. He never finished college, but he’s always been able to find a job until recently.

My friend just emailed to say that he’s been homeless for four days in Phoenix. I’m appalled at this. I’m sitting in my luxury condo knowing someone I grew up with is suffering. I could Western Union him some money, and probably will, but I don’t know if this is any sort of long-term help.

I’m trying to decide what I should do to help get him set up again. I can see on Craigslist that there are rooms for rent by the month in places that don’t cost much money. I just want him to have a roof over his head and some stability so he can find another job, retail or otherwise. I don’t know of any addiction problems (other than cigarettes); he never did drugs in his teens or twenties, and he isn’t a huge drinker. He’s meeting with a job counselor at the shelter soon.

Have you ever had an experience like this? With so many people unemployed and so many homeless, what do those of us who are well off do when confronted with someone we know in this position?

Have I ever had an experience like this? Not exactly.

I’ve certainly had childhood friends who ended up in trouble, financial and otherwise. (In fact, it was the death of my best friend from high school that put into motion massive changes in my life three years ago.) It’s always difficult to know how (and how much) to help.

Those from the tough love camp say, “Never lend money to family and friends. Don’t give financial help.” And, of course, they have a point. You don’t want to enable bad behavior, and you don’t want to create rifts in the relationship over a few hundred dollars. There have absolutely been instances where I’ve refused to provide financial help in cases where I thought doing so would create more problems than it would solve.

Having said that, I’m not much of a tough love type of guy. I’m a softie. If I were in a pinch, I’d hope my friends would pitch in to help me out; in turn, I usually do what I can to help those with financial problems. I take a lot of flak around here for not donating much to charity, but I’m pretty free with my money when it comes to people I know. Helping a friend with financial problems makes me feel good, and I hope it helps these friends find their footing.

What can Evan do in this case? What should he do? Only he can make that decision, obviously, because only he knows how much he trusts his friend, and only he knows how much money he can afford to lose. But surely there’s some general advice we can offer. And there are probably some GRS readers who have first-hand experience with this sort of thing.

Have you ever been homeless? Known somebody who was? What helped with the situation? What can the average person do to help a homeless friend? What would you do? Do you have any advice for Evan? Should he give his friend money? Rent him an apartment? Help him find a job? What advice can you offer?

Note: One great resource for situations like this is Donna Freedman’s GRS post about how to get help when you’re unemployed or underemployed. The article is a year old, but it’s packed with practical tips for those in trouble.

Update!
Evan has been posting more information in the comments below. His are the highlighted comments.

Also, Becky Blanton wrote to share a TED talk she gave about the year she was homeless. Here’s a video of that presentation:

Blanton also pointed to a free e-book she created called Homeless for the Holidays.

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