With grace and kindness.

By Catherine Newman
Updated August 20, 2015
Richard Clark / Getty Images

Real Simple’s Modern Manners columnist Catherine Newman, etiquette expert and author of the parenting memoir Waiting for Birdy, helps you master the toughest conversations.

My dear friend has a teenage son whose behavior I find troubling. He is often antisocial, complains constantly, and has a fascination with firearms. As a result, I have become uneasy about my family going to their house. (My kids, too, have noted this boy's social awkwardness and bad attitude.) My friend has gotten therapy for her son. Still, I know that she would be terribly offended if I implied that I was worried about having my kids around him. How should I handle this tricky situation? —S.H.

First things first: If the boy has access to guns that are not properly secured, then you need to keep your kids out of that house, says Boston-based psychologist Lawrence J. Cohen, the author of the book The Opposite of Worry: "Your obligation to protect your children is more important than not hurting someone's feelings." In that case, you should tell your friend that you are not comfortable being in a home with accessible firearms. But if weapons aren't the issue (and the teen just has a creepy demeanor), you may be able to avoid a confrontation.

Your children don't want to spend time with this kid, it seems. So don't make them. Arrange to see your friend one-on-one at a restaurant or at a movie. And if she tries to get both families together, beg off, claiming scheduling conflicts.

Thankfully, there is every possibility that this teen is going through a dark phase, one that he will pass out of in the near future.

In the meantime, be there for your friend. Since she has sought help for her son, she knows that there is a problem. Be as sympathetic as you can, as you would hope her to be if your roles were reversed.

I have a friend who has had some cosmetic surgeries done recently, even though in my opinion she didn't need them. Since having the surgeries, she seems fixated on her own image. She keeps saying how good she looks and makes excuses to whip out her phone and show off her selfies. I'm more than happy to look at her pictures now and then, but I want to talk about other things—and my own life, too. How do I point out that she's focusing a bit too much on herself? —S.S.

If you're game, indulge her vanity briefly, saying something like "You were gorgeous before, and you're gorgeous now." Then redirect the conversation to a mutual interest: work, travel, books you've been reading. Or directly bring up the topic you've been most keen to discuss with her: "Now, there's something I wanted to tell you about my home renovation/my mother's visit/ my next vacation." Vanity is a tedious and high-maintenance trait, but ideally her enthusiastic narcissism will wane once the novelty of her new look wears off.

My son's best friend confessed to me that he stole some stickers after going through my desk drawers one year ago. (I had always wondered what had happened to those stickers.) During his confession, I told him I was very disappointed that he took something that didn't belong to him and also that he went into my desk without permission. I asked him to tell his mother, too. My question: Should I have a conversation about this incident with her? I feel as if I should talk to her, but I've hesitated because she is going through a hard time. (She and her husband are getting a divorce.)—R.D.

Pursuing this any further would be like beating a dead (sticker-thieving) horse. This child, bless him, actively confessed his wrongdoing: He felt bad about the stickers for an entire year, then summoned up the courage to speak to you. It sounds like whatever lessons there are to learn—that it's wrong to take something that doesn't belong to you and proper to take responsibility for your actions—he has learned already.

Additionally, if his parents are in the process of splitting up, this is a kid who's in a lot of pain right now—more in need of compassion than censure. Instead of punishing him more by dragging his unhappy mother into the mix, consider positively reinforcing his bravery. You can say, "I just want to say how impressed I was that you came forward about the stickers," when you next have a moment alone. "I know that took guts." Because it did. And the better he feels about himself, the better he'll behave.

My aunt is a wonderful and highly intelligent woman. However, I fear that she has a drinking problem. I rarely see her without a beer in her hand. She drinks or shows up drunk at inappropriate times and places, including a recent funeral. She also tends to be rude and put people down when she has been drinking. I don't want to be around her when she drinks, which leaves few occasions when I can spend time with her. How should I proceed? —M.M.

First you need to decide what you want to do about your aunt's drinking, says Lydia Elison, a psychiatrist based in western Massachusetts who frequently deals with addiction issues. Because you do have a choice, says Elison: "Do you avoid the situation by not seeing your aunt? Or do you say something to her?" If you opt for the latter, Elison recommends that you take a few preliminary steps. Download an alcoholism-screening questionnaire called CAGE; look up the times and locations of nearby Alcoholics Anonymous meetings (aa.org); and enlist family members and friends of your aunt's who share your concerns about her drinking. Then, armed with this info to give your aunt and with other people to back you up, schedule a time for you all to talk to her.

During this conversation, you may want to focus on pointing out instances of heavy drinking and how you felt about them. For example: "The other night, after you were drinking, you said rude things that hurt me." You don't need to diagnose your aunt's problem; you need to describe the way her drinking is harming your relationship. Elison says, "Spend a lot of time saying how much you love her, how much she matters to you. Shame, whether conscious or unconscious, is often a factor for people struggling with alcohol abuse. Help her see this as an illness and not a character flaw."

Hopefully your aunt will listen to your concerns and take action. Regardless of the choice she makes, you should be proud that you are doing everything within your power to assist her.

My sister-in-law is expecting soon, and I am invited to her baby shower, which is being hosted by some of her family and friends. However, my husband and I are undergoing painful infertility treatments, and a baby shower is more than I can bear to face right now. So I recently declined, assuming that my in-laws would understand, since they know about our situation. I also plan to have a lovely gift and card delivered to the shower. Nonetheless, they are furious with me for "ruining" her event. What should I do? —T.T.

I'm so sorry, both that you're in pain and that your relatives are layering guilt onto your sadness. You have behaved with care and integrity and have handled a difficult situation in the best way possible. Something that really could ruin your sister-in-law's upcoming shower would be for you to burst into tears in the middle of it—a possibility that you wisely chose to forestall. It's mystifying that your relatives cannot, from their flush place of expectant joy, extend a little sympathy your way. The fact that other people are behaving badly doesn't mean that you have done so yourself.

However, if you feel that anything has been left unsaid with your sister-in-law, and particularly if you think that she doesn't fully understand what you are coping with, contact her directly after the shower. "Forgive me if my absence spoiled your event in any way," you could write to her. "I'm thrilled for you, but I've been having such a hard time with my fertility issues that I didn't want to risk tarnishing your joyful occasion. I'm sure it was a wonderful party, and I'm sorry to have missed it." Then be sure to congratulate the couple on their new arrival when the time comes. I'll keep my fingers crossed that your time is coming, too.

My daughter has stage 4 breast cancer. Oddly, my family and friends never ask me how she is doing. I'm not sure why. I neither get upset nor go into graphic detail when I talk about her situation—not that they would know, since they don't ask. I am finding this conversational omission increasingly hurtful. Should I tell people to stop avoiding the topic? —L.L.

I'm so sorry. I can only imagine the depth of your pain and fear, and I wish your community were acting more supportive than skittish. My guess is that folks care deeply about you and your daughter but lack courage. As crazy as it sounds, people worry that they're going to remind you of a difficult situation that you're not otherwise thinking about (as if!) or that they will say the wrong thing.

Tell your loved ones explicitly what to say to you—not just because it will make you feel better but also because it will be a gift to them. I would do this via a group e-mail: "What my daughter and I are going through is so hard. I understand that you're nervous. It might feel awkward to talk to me about her illness, but please do. I'm asking you to show your concern and love by inquiring about her whenever we see each other." Let them know that they'll be helping you—and reminding you of all you have to be grateful for, even in the darkest days.

In the months following the death of Robin Williams, many mental-health "experts" in my life have come out of the woodwork. Not long ago, a coworker began giving a loud diatribe about suicide's being a sin and about how the person who committed suicide would be sent to hell. Afterward, I explained to her that my own child had taken her life and that I found her opinions to be very upsetting, at which point she apologized. Still, the confrontation left me almost in tears. Plus, I really do hate to make other people feel bad, even when they are being insensitive boobs. How should I handle these types of painful moments? —D.F.

I am so sorry for your loss and can only imagine how your pain is redoubled by the careless comments of people who don't know your family history. I'm quite certain that folks wouldn't want to blunder by upsetting you if they could help it.

As a service to them, to yourself, and to the many others who have dealt with a loved one's suicide, would you consider trying to preempt the offense? As soon as one of these "experts" starts opining, say, "I'm sorry to interrupt, but before you say anything further, I think you should know that I lost a child to suicide." Then, if you wanted to, you could dispel some of the most common misperceptions of suicide. Or you could add, "There are a lot more of us around than you might think, so it might be best to be cautious when you speak publicly on this issue." (This is true for most touchy, personal issues, in fact: It's important to remember that we don't know everything that matters about the people with whom we share our workspace.)

It's completely understandable to feel aggrieved when you're grieving. And you're right to stop an insensitive conversation in its tracks.