DEAR HARRIETTE: My sister's high school boyfriend just contacted me via Facebook and asked me about my sister. He said he wants to be in touch with her after something like 40 years. My sister is single now, but I don't know if I should connect them. This dude is seriously a blast from the past. My sister is kind of weird about inviting people into her life -- just bringing it up may start an argument. She is pretty reclusive these days. That's part of why I thought I might connect them. Maybe he would make her smile. Do you think I should set up a blind date kind of thing for them? Should I just tell her and see if she's interested? Or should I leave it alone? -- Sisterly, Salt Lake City, Iowa

DEAR SISTERLY: Do not surprise your sister with a blind date. That would be awkward for everyone and could easily backfire. Be respectful to her and let her know that her high school beau wants to be in touch. Tell her how he reached out, and suggest that you share her phone number or email address with him. Being in touch does not necessarily mean dating or even seeing each other. It can mean an email or phone call. She may be open to something that simple.

If she says yes, great. Make the connection. Because she may decline, do not promise anything to the ex-beau. If she does decline, tell him you will deliver the message and if she wants to, she will reach out.

DEAR HARRIETTE: My son just informed me that he wants me to get him some really expensive earphones for Christmas. He is 10. I know that he and his friends listen to music on their iPods, but I think the price is excessive. He pointed out that he would be happy with that gift alone if I chose to buy it for him rather than the range of things we usually buy. He has a point. I definitely spend more than the $100+ that the headphones cost, but I just usually buy a lot of things. Should I honor his request? It still seems like a lot of money. -- Unsure, Washington, D.C.

DEAR UNSURE: If it is true that you spend generously on your son's holiday gifts and he is crystal clear about his one desire, you may want to consider it. Part of the experience that parents should have with their children is teaching them about choice and value. He wants an expensive item. Explain how you would expect him to take care of it and that if he breaks or loses it you will not replace it. Your choice to buy him a broad range of things does not seem to be his choice now. This means that you and he have to be disciplined. If you tell him that he can have only that one item or that one and a few extras, stick to that. Explain to him that this is how you can honor his desire. Teach him the power of choice by being a parent of your word.

DEAR HARRIETTE: Your advice to "Frustrated" in Syracuse, N.Y., was OK, but I strongly recommend the following: First, do not communicate with the Internal Revenue Service yourself. Second, hire an accountant to work on the debt to determine if it is justified and to possibly get the amount reduced. Let him/her communicate with the IRS. Third, allow the accountant to put you in touch with a good tax attorney who may be able to get the debt eliminated entirely. Fourth, and maybe most important, NEVER accept what the IRS says you owe, because once you have made them work so hard to no or little success, they won't bother with you in the future. -- Wiser, Kankakee, Mich.

DEAR WISER: I completely concur that when you have a challenge with the IRS, you should bring in professional support. A tax accountant can help you go through all of the paperwork and has the eye to spot any inconsistencies as well as the experience to know when a tax law is appropriate to use or not. The tax code changes all the time, and it is best to have a professional support you in an audit or any other tax conflict.

DEAR HARRIETTE: One of my best friends and I talk all the time. We have a good friendship, but we rarely see each other. The other day, I sent her pictures of my home, something I never do because I feel like it is always kind of messy, which is why I hardly ever have people over. She had convinced me to show her. Right away she started telling me what I should do with my stuff. That is the last thing I wanted or expected from her, given how many conversations we have had about our homes. She keeps asking me if she can come over, but now I really don't want to invite her. If she is criticizing me about a photo, I don't think I can take her in-person comments.

I am not in hiding, by the way, or delusional about my cleanliness. I have been working hard to get my place together. But I do not want anyone passing judgment, especially a good friend. What can I say to her? -- Messed Up, Syracuse, N.Y.

DEAR MESSED UP: It is likely that your friend started in with her suggestions with the intention of supporting you. It is understandable, though, that you did not experience it as that. You can tell her that you are not ready to have her input.

But do not stop there. Make a schedule for the next month giving yourself a task to accomplish each day. Methodically clean up your home, and toss out anything you can. When you feel comfortable, ask for help. You may want to get a service to come in to do some heavy cleaning. You can call a charity to come pick up the items you want to give away. When you are more comfortable, invite your friend to visit and let her know you do not welcome her comments.

DEAR HARRIETTE: I have a twin sister. We have never been attracted to the same types of men, which has really helped us through the years to avoid conflicts. Now I find myself interested in one of her exes. They dated years ago for a very brief time, and he recently asked me out for dinner. I don't know what to do. Please help! -- On the Fence, Washington, D.C.

DEAR ON THE FENCE: Check in with your sister. Tell her that this man called you and asked you out, and ask her if she is OK with that. She may not care at all. But it is wise to find out. The last thing you want is to get involved with your sister's ex and hurt her feelings. A date is not worth damaging your relationship with sister.

DEAR HARRIETTE: I ran into a financial snag a few years ago, and a dear friend bailed me out. She said I didn't have to pay her back because that's what friends are for. But now that I have the money, I want to pay her back anyway. As I was thinking about how to broach the subject with her, I remembered that she told me that if and when I do come into the money that I should pay it forward. Do you think I should ask her if she has a favorite charity or something where I can donate the money? Or should I pick one and tell her that I was able to do it. I want her to know that I'm on good footing now and that I want to do right by the investment she made in me. -- Pay it Forward, Boston

DEAR PAY IT FORWARD: It is likely that your friend wants only the best for you and does not need to know about how you are using the money that you now have to contribute. She gave you that leg up when you needed it with no strings attached to her.

Will she be happy to hear about your stability and ability to pay it forward? Yes, because it shows that you are in a good place in your life and that you are thinking of others. Rather than asking her where you should send the money, do your own research. Is there someone in your life who is in financial need and whom you can help discreetly? If so, go ahead and offer the person the money he/she needs and give the same mandate -- when possible, pay it forward.

Next, reach out to your friend through a handwritten note and thank her again for her generosity several years ago when you were in financial straits. Tell her that you are now in a good place and that you took her advice and helped someone else who needed support. You can follow up with a call to check in, but a note will concretize the gravity of the situation and reveal your completion of the cycle of giving in a beautiful way.