Question: I’m planning to ask my girlfriend to marry me, and here’s the problem: I’m building us a new home, so cash is tight. While I want to give Stacy a diamond solitaire, I don’t have the money. My plan is to buy her a synthetic “diamond,” then replace it with a real one as soon as the house is finished and I get a little ahead. Must I tell Stacy the truth about the ring up front, or can I wait until I give her the real diamond?

Our Answer: Tell her when you give her the ring. Unless Stacy is different from most women, she’s going to show off that ring to all her friends and family. Imagine how foolish she would feel, then, if she were to learn later that the stone she’d told everyone was a perfect diamond was nothing more than a perfect fake. She’d be humiliated, of course, and you’d look like a loser for putting her in that situation.

That’s not the only problem with your plan. Spouses need to trust each other, and Stacy is going to have trouble trusting you if she learns that your first act as a prospective husband was to mislead her. For reasons that should be obvious to everyone looking to tie the knot, it’s a bad idea, and you should forget it.

That said, we applaud your financial priorities. Putting the house ahead of the bling is certainly prudent, and we wonder if you’re not selling Stacy short in assuming she doesn’t share your sense of responsibility. Why don’t you take the high road here and ask her what she thinks about all this? You may be pleasantly surprised by her answer.

Question: My brother’s a terrible cheapskate. Two examples:  He gave my son a two-dollar comic book for Christmas, though we always give his kids nice presents.  And I paid for most of our father’s 65th birthday party because he claimed many of the expenses, like nice wine, were unnecessary.  I say my brother’s penny-pinching is unfair to other people, but he says the way he spends his money is none of my business.  Who’s right?

Our answer: That depends.  Is your brother truly a cheapskate or merely a tightwad?

Here’s what we mean.  Your brother isn’t required to spend his money on more expensive gifts, more expensive wines or anything else just because that’s what you’d prefer.  And that’s true whether he’s Donald Trump or Donald Trump’s driver.

There’s a big difference, though, between being tight with money and failing to spend what an occasion calls for.  If your brother was unwilling to pony up for his share of the food and drink that others in your family agreed would be customary for your father’s party, then he’s a cheapskate.  And if that’s the case, it is your business.  You have every right to protest and every right to insist on being reimbursed.  

Now about those nice presents you’ve been giving your brother’s kids: Has he happily accepted them and said nothing, or has he let you know he thought they were extravagant?  If he’s said nothing, you again have a right to complain.  Because unless he’s told you he doesn’t want to exchange expensive gifts, your brother has no business reaping the benefits of your willingness to do what he won’t - spend money on other people.