My New Boyfriend Offered to Pay Off My Credit Card Debt. Help!

I started dating a new guy two months ago. Things have been going very well. I also have $5,000 in credit card debt that I am working hard to pay down. The subject came up when he asked me why I always use a debit card. (I don’t want to add a penny to my credit card balance.) He comes from a very wealthy family; I do not. Out of the blue, he offered to pay off my entire balance in exchange for a zero-interest loan that I could repay to him over time. This is obviously attractive compared with the 25 percent interest I now pay. But yikes! This is huge. Is it wildly inappropriate that I am entertaining his offer?

GIRLFRIEND

Mixing business with (new) romance is a risky cocktail, but that doesn’t necessarily mean you should refuse your boyfriend’s offer. The two of you should discuss it carefully. For starters, thank him! Even if you decide against accepting his proposal, it probably came from a kindhearted place: He saw that he could make your life much better at relatively little cost to himself.

The practicalities are easily handled: Create a simple written agreement with clear payment terms to govern the loan in case your fledgling romance sours. The repayment must be independent of your relationship. Also, confirm with an accountant that the dollar amount here is too small to trigger any gift tax, or to count as reportable income.

That leaves my primary concern, which only you and your boyfriend can assess: Will taking this loan make you feel indebted to him — beyond the $5,000? Will you defer to him on other issues because you “owe” him? Will he feel entitled to that deference? If this is a good relationship (and you can both compartmentalize), you may be able to handle this extra wrinkle; if not, the loan may cause serious problems. Talk it out together and then decide.

Like Water Off a Slicker, Let This One Slide

My wife bought a relatively inexpensive rain jacket she liked so much that she bought another one for her sister. (It wasn’t a special occasion; she just gave her a gift.) Her sister returned it promptly to the retailer, and a credit was issued to my wife’s credit card. Now, her sister says we owe her the cost of the jacket and should send a check in that amount. My wife wants to do it to keep the peace. You can imagine my response. Advice?

HUSBAND

I agree that your sister-in-law’s request is odd. You and your wife don’t owe her anything. But do you know what I find even odder? That you want to interpose yourself between two sisters.

I get your desire to stop an injustice here, and I think it’s sweet that you want to protect your wife from her grabby sister. But there’s not a lot of money at stake, and your wife knows her sister better than any of us. If she wants to give her cash “to keep the peace” in an important relationship, I would defer to her. She’ll know better about gifts to her sister the next time.

‘Rebate’? Think of It as a Wedding Gift to Your Guests.

My fiancé and I are having a destination wedding. We chose a reasonably priced resort, but the cost to our guests will still be substantial. In its marketing materials, the resort mentioned six free rooms as part of our wedding package, but those rooms turn out to be a cash rebate for the value of six rooms that we will receive after the wedding. We had intended to give those rooms to family and friends of lesser means. Any ideas about what to do now without wounding anyone’s pride?

BRIDE

I don’t want to sound like a scold, but you may have hurt your invitees already, by inviting them on an expensive vacation they can’t afford but feel obliged to take anyway. If you and your fiancé have the resources to pay for this event, you probably have the cash to advance the forthcoming rebate, too.

Offer free rooms to family and friends just as you intended, even though you won’t receive cash back from the hotel until afterward. It’s simply a timing issue. As you noted, you are asking your guests to shell out a lot of money (on flights and food and drink). I would communicate gently with all your invitees that you understand entirely if your destination wedding is not practical for them.

His Shred Time, Your Bedtime

I have a good friend who plays in a heavy metal band. Occasionally, he sends out email blasts announcing shows, but his band usually takes the stage after 9 or 10 p.m. That’s too late for me! I go to bed early, and I have little kids who go to bed earlier. I know my friend understands this. Is it better to send regrets explaining why I can’t come, or is that ruder than being vague about it?

FRIEND

Tell the truth. I think it’s kind that you respond to your friend’s email blasts. If I were he, though, I might interpret a “vague” excuse as lack of interest on your part when the actual reason makes perfect sense. So, be honest — and rock on!

For help with your awkward situation, send a question to [email protected], to Philip Galanes on Facebook or @SocialQPhilip on Twitter.