Dear Dave,

Our daughter wasn’t very responsible with money until she read your books. Now, she has really started turning her life around. Recently, she learned she needs to have some expensive dental work done. Since she just started trying to manage her money well, she doesn’t have enough saved up for the procedure or dental insurance right now. Do you think we should help by loaning her the money?

— Dianne

Dear Dianne,

I like what you’ve told me about your daughter. She doesn’t need to worry about dental insurance though. You almost never get back what you put into those policies. It’s the kind of stuff a good emergency fund will cover. If she has invested her time and money into what I teach, I’d say she’s pretty serious about getting her finances in order.

If it were me, I’d make the money for dental work a gift, not a loan, for turning her financial life around. In your description you never mentioned anything about your daughter being lazy or unwilling to work. You talked about a young lady who’s just starting to build her life, and you’re rewarding smart choices. I think that’s a great idea and will have a major positive impact!

— Dave

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Dear Dave,

My brother and I recently received an inheritance after our mom died. He’s never been very good with money, so I was proud of him when he used his portion to pay off his debts. But then he went out and financed a van that I know he still can’t afford. I’m afraid he’s falling right back into the same old money problems, but I don’t know how to talk to him about it.

— Diana

Dear Diana,

I’ve learned, after years of writing books, doing a radio show and trying to educate folks about their finances, you can’t make people listen to you. Even with what I do for a living I don’t throw my opinion around unless someone asks.

I think you’re smart for realising there are some boundaries here. But there’s no reason you can’t create a situation where he can ask your opinion. You might begin with talking about some of the mistakes you’ve made in the past. This could help him connect with you, and feel more comfortable opening up about his own situation. Once he realises you haven’t repeated the same mistakes, and have a better life for it, he might just ask how you did it. Then, the door is open!

But you can’t become preachy every time someone does something dumb. That will only hurt their feelings and cause them to tune you out completely.

—Dave

* Dave Ramsey is America’s trusted voice on money and business. He has authored five New York Times best-selling books: Financial Peace, More Than Enough, The Total Money Makeover, EntreLeadership and Smart Money Smart Kids. The Dave Ramsey Show is heard by more than eight million listeners each week on more than 500 radio stations. Follow Dave on Twitter at @DaveRamsey and on the web at daveramsey.com.