Give money to a jobless friend?

NEW YORK (Fortune) -- Dear Annie: I have a very close friend who's been out of work for almost a year now. He was my college roommate: I've known him for almost 20 years and, for about half that time, we worked at the same company. Then he got laid off. Last week one of my kids told me that my friend's youngest son missed out on a ski trip with the rest of his class because of the expense, even though the cost was minimal (to those of us with jobs).

A couple of other buddies and I are thinking of pooling some cash and giving it to our friend, just to tide him and his family over until he gets another job. But he is a proud person and would probably be insulted by what he would see as charity. Should we make the offer anyway? Any thoughts from you and your readers on what else we can do to help? -- Bystanders

Dear Bystanders: You are doubtless not the only one wondering. As of February, 6.1 million Americans had been unemployed for longer than six months, just below January's 6.3 million record high, which was the worst tally since the Bureau of Labor Statistics began counting in 1948.

Almost everyone, these days, knows someone who has been jobless for a painfully long time -- and, like you, many of us are at a loss as to how to help. Even if it doesn't involve money.

"Especially when the person who is out of work is a former colleague, there is an element of 'survivor guilt' that often keeps people who still have jobs from even picking up the phone and saying hello," notes Thom Singer, a personal branding expert based in Austin, Texas, who has written six books about networking.

"They don't know what to say, so they say nothing. But it is terrible to get laid off and hear nothing at all afterwards from former co-workers. It creates a tremendous sense of isolation and loneliness."

So Rule No. 1, Singer says, is: Don't hesitate to call or e-mail, just to say hi. "And when you do," he adds, "don't start right off asking how the job hunt is going. Nobody wants to be a downer by always having to say they haven't found anything yet." Instead, talk about "other interests, other things your relationship is based on" -- sports, movies, your kids, your upcoming college reunion, or whatever.

A few other tips that may help:

Stay in touch. "While it may be hard to grasp when you have a job, seeing and hearing from friends, including former colleagues, is vitally important to someone who has lost a job," Singer says. "Your regular calls, e-mails and visits make a difference in keeping people feeling motivated and connected."

Talk up your friend to other people. "If you want to help someone find a job, then obviously bringing them along to business events and introducing them to people is a good thing," says Singer. "But take it further and mention him in conversations with people who may be hiring even when he is not present." The more often you do this, he adds, the more likely it is that someone will eventually respond with, "Hey, I need that!" and ask for his contact information.

Don't let your friend give up. Looking for a job in this market is awfully difficult and discouraging. "You can help by reminding your friends of everything they have achieved and everything they have to offer," says Singer.

He notes that getting a career back on track is often a matter of sheer dogged persistence and that, if your friend shows signs of abandoning the job search, you should gently point out that "sooner or later, opportunity will knock," says Singer, "but not if he is spending his days sleeping in and watching Oprah."

Singer adds: "There are few certainties in any job hunt these days, but one thing I know for sure is that 100% of the people who give up don't find jobs."

Pick up the lunch tab (without making a big deal about it). Clearly your friend, like most people who have been out of work for a while, is watching his pennies. So when you go somewhere with him, pay his way as discreetly as possible. If he objects or seems embarrassed, says Singer, "Tell him you'll get it this time -- and when he find his next job, which he will, then it's his turn."

Which brings us to the sticky question of whether you should give your friend money to help out with living expenses. "If you and your other friends are in a position to do so, there's no reason why not," says Singer. "If your friend really doesn't like the idea, he can always say 'no.' But whether he accepts it may depend on how you make the offer."

Characterize it as a loan rather than a gift, he suggests -- albeit a loan with no interest and no formal repayment schedule: "If your friend knows he's expected to repay you when he gets back on his feet, it's not charity. It's just a little help with a rough patch." And after all, what are friends for?

Talkback: Have you been unemployed a long time? Would you appreciate a friend offering money? Any other help you wish they'd offer, or anything you wish they'd stop doing? Tell us on Facebook, below.