Dear Eric: During our morning walks, my husband and I became acquainted with “Ron,” a homeless man who always sits on the same bench and always has a cheery hello. During the holiday season, we decided to gift him a box of homemade cookies and a Christmas card with $200 in cash slipped inside. I’ve imagined him treating himself to a decent dinner or buying something nice. We knew nothing about Ron, except that he seemed sweet and sober and appreciated our little gifts.

Recently, from several reliable sources, we’ve discovered that Ron has been sending money, including his VA checks, to a woman in China in the hope of getting her to come to America and marry him. People have repeatedly tried to tell him that this is an internet scam, but he refuses to listen.

I find it upsetting that our money is being handed directly over to a scammer somewhere. My inclination next holiday is to continue to hand him the cookies and the card but not the cash. I figure it’s just $200 less for some heartless con artist to steal.

My husband, however, objects. He says it’s none of our business how Ron spends his money. If this gives Ron purpose or pleasure, then who are we to interfere? Our reward should be in the giving and nothing else. My compromise is to give Ron a gift certificate, perhaps to a grocery store, but my husband feels that even this safeguard is too judgmental. What is your opinion?

— The Christmas Judge

Dear Judge: We don’t get to choose how other people make use of our gifts, especially strangers. Since you don’t have a relationship with Ron beyond these very generous gifts, you’re not in a position to safeguard him. I’m not wagging my finger, but it’s notable that you know nothing about him and you heard about the supposed scam from others, not from Ron. He’s not shared this part of his life with you.

What you might do is ask him, “what do you need?” or “is there someplace from which you’d like a gift card?” This way, you can be more confident that you’re meeting him where he is without trying to police his spending.

Dear Eric: I have a friend who is driving me and other friends to the brink with her persistent negativity. This has been going on for years but is much worse lately.

We are all retired, and this friend is substantially better off financially than the rest of us. Despite this, everything is a litany of “poor me” and nonstop negativity. No one else has suffered grievous losses as she has (we have). No one else is as burdened with problems as she is (we have our own issues, and deal with them). No one experiences as much pain, suffering, loss, misfortune or tragedy as she does.

Literally every conversation ends up being her listing a multitude of problems, all featuring her as the victim. When we try to gently point out that they are financially secure, or have many blessings to be grateful for, it’s just a doorway to yet more complaining, whining and “poor me.”

It’s clear she’s depressed, and it’s also clear that the medications and counseling she’s receiving are not helping. We’ve tried patience, listening, kind boundary-holding on topics, and redirection.

It’s to the point where some friends have stepped way back from the relationship, and where several of us are questioning why we continue on. This woman can be kind, generous and caring but rarely, and there’s little joy in any of our relations with her. Help, please.

— Overwhelmed by Negativity

Dear Eric: My sister’s daughter is getting married in the fall. My 20-year-old daughter has not been invited because it is “adults only.” This upsets both of us because she is close to her cousin.

When I asked if she could attend the wedding ceremony, I was told that I wasn’t even invited to the wedding ceremony because it was immediate family only, although the seven bridesmaids will outnumber the wedding guests.

Now I will be driving several hours to attend the reception. It feels like a long trip just for dinner. Just sending a gift will upset my sister. I am not sure how to handle this situation.

— Reception Only

Dear Reception: I do empathize with your disappointment about not being invited to the ceremony, but on a technical level the difference between a reception-only experience and one that includes the ceremony is probably only an hour, maybe an hour and a half. Yes, that’s a crucial hour, emotionally, legally, religiously, if they’re so inclined. But it might help you to think of the reception not as lesser, but just different.

Now, this doesn’t mean you’re required to go. If you find that thinking of the reception in a different way doesn’t assuage your hurt feelings, that’s fine. You can decide to send a gift and spare yourself the drive. But there probably isn’t a way to skip the event and not offend your sister.

I often get questions about weddings; people have different requests and requirements of their guests. It’s good for marrying couples to assume everyone’s best intentions and best efforts and be understanding of their guests. It’s also great for guests to say to themselves, this is their special day, and I want to be there to help make it special.

Tell your sister you want to make it special, but you’re feeling like an afterthought. Maybe she has some insight.

Dear Eric: I am recently widowed and have never seen my problem addressed. My spouse was a wonderful person. I now have the remnants and reminders of our 38 years together literally everywhere. Hobbies, clothes, boat motors, guitars, golf clubs, yard tools, woodworking supplies. My children would love for me to continue living with it all. How do I separate from it?

— Mementos

Dear Mementos: I’m sorry for your loss; mementos can be a comfort or a hard reminder. And sometimes they’re both. The complicated feelings you’re likely feeling aren’t unusual. There are options. Reach out to a senior downsizer or a professional organizer and enlist their help. They won’t start giving things away right off the bat. Rather, they’ll help you think through what you want your space to look like and they can help navigate conversations with your kids about handing things off.

It sounds like your children are experiencing part of their grief as sentimentality. That’s completely understandable. But the solution isn’t for your house to remain a museum. They can take mementos that mean something to them. Then you all, as a family, can thank the other mementos for what they gave to you and what they represent, then release them to another life.

Take your time with this. I imagine it’s overwhelming being surrounded by reminders of your fresh loss every day. Start small, perhaps by creating a space — a room, a corner — that is just yours to fill up or leave empty as you get to know this new version of yourself and process your feelings.

Dear Eric: This is in response to “Rambling Relative,” whose 84-year-old mother had no cognitive issues but had begun rambling and repeating herself on their phone calls.

The letter writer may want to try this:

When she starts talking about people or events you don’t know anything about, get a pad and pencil and write down notes. Make sure you tell her you are doing this so maybe she will get to the point. (You can repeat each one back to her as if you are trying to get it right.) If you are a praying person, you can tell her you will take time to pray for them during the week.

The next time you talk to her, go down the list and ask how each one is doing. If she starts to ramble on about one of them, summarize by saying, “So no improvement there,” or “I’m glad so and so is doing better.” Then move on to the next one. After you finish the list, tell her something about your life, or ask her how she likes the weather, etc.

Dear Eric: I live in an apartment with my 22-year-old daughter. She had a really bad high school experience that was broken up by Covid, so remote learning didn’t go well either. She eventually got her diploma but since then has not been able to find a job. We are going on about a year and a half now. She applies but doesn’t even get interviews.

This is going to sound selfish, but I want to move away with my boyfriend of seven years so that we can start living our life together (we do not currently live together). I know my daughter is an adult, but she is far from self-sufficient and makes no money to pay rent/bills/groceries.

I cannot kick her out onto the streets; I don’t have it in me to see her struggle like that. I can’t take her with us because they don’t get along. I’m kind of at my wits end here because I don’t know how to change my situation so that I will be able to leave with my boyfriend and also make sure that my daughter can take care of herself. Please, help me.

— Feeling Helpless

Dear Feeling Helpless: Pull your daughter into this conversation. Be honest with her about what your goals are and ask her what her goals are. And then work together to make a plan. It’s been kind and loving of you to provide for her as she struggles with independence. But it will actually be empowering for you to engage her, adult to adult. She’s going to need these skills whether or not she gets a job.

Maybe she needs training in a specific field or further education; maybe she can cobble together income from gig work. Maybe there are other relatives or friends that she can assist for money or in exchange for housing. I’m not saying this will be an easy process for her, or for you. But something needs to change in her life, and you want something to change in your life. The first step is asking her, “what do you plan to do and how can I help?”

Dear Eric: I have a soft voice that has been criticized by many. I took a required speech class in college, and the instructor made up an emergency and asked if anyone would believe me if I told them about it.

I overheard my principal tell a colleague, “It’s a wonder she had any control over her (elementary) class with that voice.” I am so tired of being talked over by others. Sometimes, I have to start saying something three or four times before people listen. Sometimes, I just give up. Sometimes, I feel like I should act like a child, raise my hand and wait to be called on. Help!

— Quiet as a Mouse

Dear Quiet: Despite what your principal said, I’m presuming you do have control over your elementary school class. You’ve developed tactics that don’t rely on your voice’s volume. Give yourself credit for finding other ways to command attention, teach material and maintain order. Perhaps there are ways of applying some of your classroom skills in other areas in life.

Also, look into a class or training with a vocal coach or acting teacher. The voice is an instrument and, like any other instrument, “loud” isn’t always the best setting. Consider a piccolo or a clarinet; when played correctly, they can be quite arresting without very much volume. Similarly, a teacher trained in the voice can work with your specific instrument, show you its features — your vocal cords, your diaphragm, your breathing, etc. — and guide you in ways of using it effectively without having to shout.

Dear Eric: My husband and I enjoy hosting dinner and cards with other couples. This is also reciprocated by a few other friends. I’ve found it cringe-worthy due to the fact that they don’t want to play a game that takes some thought. It’s a game that just relies on the luck of the draw.

Dear Eric: My husband and I are in our early 70s. We’re both in good health. We have one child who is an adult and lives independently but close by.

My husband and I enjoy marijuana now that it has been legalized in our state. Between the two of us, we smoke one joint after 7 p.m. about four days a week. We also enjoy it on special occasions like holidays and birthdays.

Lately, when our adult child has been over to visit and we step away to share a joint, they’ll comment “I thought you only smoked on these days” or something to that extent. I feel like they’re keeping tabs on us, or even judging us by saying, “OK” in a disapproving way.

We are never in a “far out” state of mind after we smoke (or eat edibles). It relaxes us to enjoy music, watch a funny movie or program until we get tired and go to bed. If we had to go somewhere in an emergency, we would Uber it. Our adult child is aware of this.

I’d like to mention that up to a year ago, this adult child smoked marijuana with us at times. They had some health issues that have since been taken care of. They’re not anti-marijuana but seem to be focusing on our use. It makes me uneasy in my own home when this happens. Sometimes we have to “sneak” it in while they’re visiting to avoid any questions/comments.

When these comments start coming, I want to tell this adult child that it’s none of their business what we do in our home. I feel policed and judged by them. I also feel like I don’t have to explain anything. Any advice?

— Senior High

Dear High: Bring it up to your child in a neutral manner and ask your adult child to have a discussion with you about it. Start by saying something like, “I’ve noticed that when we smoke, you often comment.” Then explain how you feel when that happens and ask them if you’re reading the situation in the way they’re intending. Something like, “when that happens, it makes me wonder if you think we’re using marijuana too much. Do you?”

The goal of the conversation is to get and give more information. Maybe your child’s response is more about their own journey, and they don’t realize how they’re coming off. Or maybe they do have concerns. If the latter turns out to be the case, it’s better for both of you that those concerns are verbalized. It’s up to you whether you agree with those concerns and whether you decide to make a change. But by opening the door to a conversation about what’s being said, you free both yourself and your child from interior narratives that can cause resentments.

Dear Eric: My 80-year-old sister lives alone after her husband passed away a long time ago and has no children. She lies so much that it’s upsetting.

She lies to everyone around her about her previous job and even her education. She even tells the senior center that her children live out of state.

She used to be a poet and published two books, but she lied about her education in the author bios.

I’ve repeatedly told her that lying is wrong, but she refuses to listen to my advice. It’s sad that I can’t respect her like this, but sometimes I even hate her. What should I do as her sister? I want to be honest with everyone around me about my sister, but I also have to consider her pride.

— Upset Younger Sister

Dear Sister: Lying this much indicates that there’s something deeper going on. Perhaps it’s psychological, perhaps it’s emotional. Perhaps she’s trying to cope with grief or disappointment or shame. It’s not for me to diagnose.

Dear Eric: I have been a preschool teacher for more than 20 years. There are a few times throughout the year where the kids and their parents give us gifts, which of course is optional. Those occasions are Christmas, Valentine’s Day, Teacher Appreciation Week and Graduation.

I have never asked for, nor do I expect to receive gifts from the families, but am always thankful when I receive them, and I express my appreciation and gratitude for their gift.

It doesn’t happen often, but it does feel good when the families appreciate all of our hard work.

My boyfriend thinks I should be humble and modest and tell the kids and their families that I don’t want their gifts and to give it to someone else who needs them. He feels that handmade gifts are better. While I do agree that I don’t do this for the gifts, I disagree with me telling the families and especially the 3- and 4-year-old children that I do not want their gifts, especially when they are so excited to give them to me because they bought or picked it out themselves.

I feel like part of the joy is in the giving, and seeing my reaction to their thoughtful gift, and I refuse to crush the giving spirit that their families are trying to instill in their children. I’m not sure how much more humble and modest I can be.

Am I in the wrong for accepting gifts?

— Gifted Educator

Dear Gifted: Not guilty! (Bangs gigantic imaginary gavel!) Your boyfriend is putting too much thought into something that doesn’t really concern him. I don’t have to tell you how hard teachers work or how important you are to the healthy development of the children you teach. If some of the parents want to express their gratitude for the (hopefully well-paid, but usually not well-paid-enough) work you do, let them!

Gift-giving is a form of communication, and it can be quite good for children to learn one way of expressing thanks. It doesn’t sound like you’re making a huge deal out of it or creating a situation where students without gifts would feel ashamed. It sounds like this is something between you, the individual kids, and their respective parents.

Sure, handmade gifts are nice, too. But it strikes me as a bit ungrateful, and perhaps controlling, to demand that parents supervise another craft project rather than buying you a gift card. How they show their thanks is up to them.

If you, in turn, want to pass the gift on to someone else who needs it, that’s your prerogative. But I don’t think you need to protest more to the parents. Sometimes, when people want to say, “thank you,” the best response is “you’re welcome.”

Dear Eric: I have been in a wonderful, committed relationship for nine years but we do not live together. We are both advanced seniors whose families got along and were pleased that we were together.

The day before Thanksgiving his daughter, out of the blue, verbally attacked me over something insignificant. Her rant lasted 10 minutes while my boyfriend just sat there and said nothing.

I was totally surprised by her attack but even more so that he didn’t step in and say something to stop it. Her husband, on the other hand, interjected several times on her behalf.

I have been there for him for numerous hospital stays, Covid, joint replacements and the flu while his daughter only came once for two hours during his last hospital stay. I am disappointed, hurt and angry at both of them. On one hand I want to get past this but then do I really want to be in a situation where my man doesn’t stand up for me?

Dear Eric: My mother is in her last months of life. She has been cared for in her home for the last three years by increasingly expensive home health care workers. I and other siblings have suggested over and over that she be put in a care home for round-the-clock care, but our oldest sibling (we’ll call them Jimmy) has steadfastly refused, saying nursing homes let people die and neglect patients and cause massive bedsores and all sorts of terrible over-the-top excuses.

Well, now that Jimmy’s own mother-in-law is going into a nursing home Jimmy has decided it’s time for our mother to go as well.

We have had family meetings where we decide as a sibling group how to care for our mother and then Jimmy goes against the group decision. Prior to the conflict over our mother’s care, I had a good, albeit not close, relationship with this sibling, but now I’m so frustrated by the selfish choices made regarding our mother’s care that I’m ready to say goodbye forever once mom is buried.

Should I let years of bullying in regard to caring for our mother be the cause to cut off contact with Jimmy?

— Frustrated Little Sister

Dear Sister: It’s really unfortunate that Jimmy is dealing with the stress, confusion, and grief of this phase of life by refusing to collaborate and resorting to, as you write, bullying behavior. Perhaps in his mind, he’s the one keeping the ship right. Perhaps he’s grasping after a version of life that’s no longer possible. I have empathy for him and for you, but the fact is that no matter his intentions, he’s caused harm in your relationship and that needs repair.

Don’t cut him off but do have a conversation with him about the way you’ve interacted in the past. There’s no need to rehash old conflicts, but it’s fine to say something like “I didn’t like being in conflict about mom’s care. I want us to have a different relationship going forward. How can we do that?”

Dear Eric: My husband and I moved to a new city last year and were eager to make friends. We became close to another couple, “Susan and Mike,” rather quickly and saw them often. I realized after several months however that, while I enjoyed Susan’s company, Mike is not someone I am comfortable with.

He is a heavy drinker and makes sexist and racist comments that leave me cringing. I’ve reached out to Susan several times to suggest the two of us do things solo, but unfortunately, they are quite joined at the hip.

She’s reached out a number of times over the past couple of months to ask about our next get together, and each time I pretended we had conflicts but didn’t suggest alternative dates. She reached out again today and I feel bad.

I can’t keep avoiding them, but I am not sure how to best put some distance between us without creating ill will. I feel that honestly isn’t the best policy here, but maybe I am just trying to avoid the inevitable.

— Uncoupling the Couple