Relationships are … complicated. Whether it be among friends, family, spouses or acquaintances, it can be hard to navigate others’ feelings, quirks and behavior. Some turn to trusted friends for advice. Some talk to a therapist.
Others — many, it would seem — turn to professional advice columnists, some in desperation or at their whit’s end as they face a really challenging problem; others on a lark, curious to know what a stranger has to say.
Annie Lane has offered witty, common-sense solutions to everyday problems in her column “Asking Annie” since July 2016.
Here are Dear Annie’s most popular advice columns on MassLive for 2025, in descending order:
Dear Annie: My nephew has lived with us since he was 16 years old, after my brother threw him out of his house. My brother then called me to see if he could stay with us. My sister and I accepted him into our home.
He is now 35 and still lives with us. My sister and I agree he has changed for the worse. He has expressed to us he wished we were dead by now. The other day, my sister and I went out, and our nephew closed the outside gates of our home. We couldn’t get back in because of this. I had to climb a wall in my backyard and then jump over to open the gate and get into our house. I am 65, and my sister is 59.
He has gotten to be very offensive with both of us. We’ve had to lock our cats in our bedrooms because he wants to throw them out of the house (he’s done this with one of my sister’s cats before).
We’ve called the police twice, but they say they can’t do anything because he hasn’t touched us. We are afraid, and we want him out. He doesn’t work, help around the house or pay rent, either. What can we do?
—Desperate Sisters
Dear Desperate Sisters: Your nephew is extremely fortunate to have had you and your sister to care for him when his own father wasn’t willing to. But you’ve both done everything you can to support him. It’s time to focus on your own happiness and, most importantly, your safety.
With your nephew unwilling to leave the house on his own, you’ll likely need to take legal action. Eviction laws vary based on the state you live in, so your best bet is to consult a lawyer to figure out how to proceed, especially since you said your nephew isn’t paying rent. Continue what you’ve been doing in terms of keeping your personal possessions and your animals safe from him. If his behavior escalates before you’re able to remove him from the house, don’t be afraid to call the police or the National Domestic Violence Hotline at 1-800-799-7233.
Dear Annie: I often read essays about how parenting comes full circle, how the greatest accomplishment of all is raising children who grow into capable, successful adults. That sounds fine and wonderful, and I am truly happy for those families. But I cannot help wondering, what about the rest of us?
Some of us have worked just as hard, sometimes harder, to raise our children with love, structure, and purpose. I spent years going without sleep, working long hours, showing up at every school event, driving to practices, and trying to guide them toward a better life. And yet the results look nothing like those glowing success stories. My children have stumbled, struggled and, in some cases, rejected the values I tried so desperately to instill.
For me, heartache and disappointment have become a daily way of life. Instead of pride, there is judgment. Instead of recognition for the effort, there are whispers that I failed as a parent. I am told, directly or indirectly, that I “did not raise them right.”
When do parents like me get to stop being judged? When do we get to feel proud of the effort we poured into our children, even if the outcome is not perfect? When does the pain ease, and when does the blame stop?
—Failure Parent
Dear Failure Parent: Children are not machines, and parenting is not an assembly line. You can pour in love, work and sacrifice, and still watch them choose a path you would never want for them. That is not proof you failed. It is proof they are human, with free will.
Let go of the blame. Be proud of the effort you gave, even if the outcome is not the storybook ending. Your worth as a parent is not measured only by your children’s success but by the love and care you never stopped giving.
Dear Annie: I’ve been married for 23 years, but my husband’s 31-year-old son has been a constant source of conflict. He’s manipulative, turns his father against me, and has lived with us multiple times due to homelessness, jail, and house arrest. Recently, I caught him going through my purse, and he only attempted a weak apology over the phone, which I didn’t accept—so he never apologized again.
I’ve had to install security cameras just to feel safe. He has a history of failed relationships and issues with women, yet my husband refuses to see the problem because he desperately wants a relationship with him. The tension is unbearable; I have no peace at home and feel like checking out emotionally just to cope.
How do I reclaim my home and my sanity when my husband refuses to set boundaries?
—Stepson Problem
Dear Stepson Problem: You don’t have a stepson problem; you have a husband problem. His refusal to set boundaries is enabling his son’s behavior at your expense. At 31, this man is not a troubled child; he is a grown adult creating chaos in your home.
Have a serious talk with your husband. Make it clear that you will no longer tolerate being disrespected, manipulated, or feeling unsafe in your own home. If he refuses to put your marriage and well-being first, you may need to consider your own next steps—whether that means separating yourself emotionally, physically, or both.
Your home should be your sanctuary, not a battleground. Take control of your peace.
Dear readers: In light of St. Patrick’s Day, I want to share this story from “Same Boat,” who wrote a response recently to share the story of how he reconnected with his fiancee from 28 years ago. With all the twists and turns of life, his story is about as lucky as they get. May your holidays be equally serendipitous!
Dear Annie: Thank you for publishing my response to “Nostalgic and Regretful.” I wanted to share with you something I recently wrote regarding my fiancee and my love story—our “romance novel,” if you will.
We met in March 1994 at a local pizzeria. I was a cook there, and she had just been hired as a hostess. At the risk of sounding cliché, I had never seen someone so beautiful, and to this day, only my children have ever equaled that sight.
The attraction was instant, but it went beyond that. Never before had somebody had my back the way she did. She was my staunchest ally, which I desperately needed at that time. For much of the summer of ’94, I was functionally homeless, sleeping on friends’ couches or in cheap motels. I barely had a penny to my name, and yet she never wavered.
At the (quite appropriate) protestations of her family, who saw me as an 18-year-old bum, she always stood by me.
But we were kids, and I was an idiot, fearful and insecure. I listened to advice and gossip from some not-so-well-meaning people. Rather than communicating with the young woman who had been nothing but honest with me, I broke up with her, and in doing so, devastated myself. She is not one to put up with baloney, and she wasn’t dealing with mine.
We would not set eyes upon each other for nearly 30 years.
We became Facebook friends in 2009 and would sometimes wish each other happy birthday. I didn’t think much of it, as I dubbed Facebook “where old friendships go to die.”
After three failed relationships, I was done with romance. I was jaded and cynical, tired of being controlled and cheated on. Tired of my own faults, tired of putting my heart and soul into people, relationships and jobs that never put forth the same effort.
Then she popped up on my feed.
There was something curious about it: Her name was her maiden name. My divorce from my second marriage had finalized a few months prior, and suddenly, there were no chains holding me anywhere.
My curiosity wouldn’t let me go. After a little research, I discovered her divorce finalized one day before mine.
That night, I reached out and asked if she wanted to go out and get some burgers. Nothing ventured, nothing gained.
While we didn’t get those burgers that night, we did start talking again. Soon after, I started preaching again. It’s funny, because when I was in the hospital with COVID-19, I prayed that if God got me out of there, I would go back to working in the church. It didn’t even have to be as a minister. If He wanted me to scrub bathrooms, I’d do it gladly.
So, there I was, back in ministry after more than seven years away, and right after the first service, I got a text from her: “You know, I’m only 20 minutes from you.”
My son and I arrived right to the place where she was camping. “I better be getting a hug,” she said. To paraphrase Eminem, I had “traveled back to the arms of my rightful owner.”
We were set in stone that day and have been ever since. At the beginning, there were moments where I thought maybe we had been cheated out of 28 years together, but no longer. After all of the mistakes, sins and bad decisions of my life, I realized that she deserves better than the way I was at 19, 27, 38. I want to be the best version of myself for her, because she deserves nothing less. I can never say about anyone else what I can say about her: that she truly makes me a better man.
—Same Boat
Dear Annie: I spent my early childhood years with a loving foster family, and today, at age 75, I have a great relationship with my foster brother.
I lived with my biological family from age 7 until I left for college. I have one biological brother, and long story short, we are not close.
Today, I can hardly stand him or his family. He brags incessantly. He’s thoughtless, snobby, self-centered, condescending, materialistic and does nothing for anyone unless there is something in it for him. He and his wife seem to take pleasure in hurling insults at our children and their families and asking rude, intrusive questions.
My husband, children, and I want no contact with him or his family. We stopped initiating contact with them several years ago. We didn’t make any “proclamation”; we just stopped contacting them, and they didn’t seem to notice until recently.
We have not answered their calls and don’t want to. We feel we should, at this time in our lives, not have to deal with them. And yet, maybe I should speak to my brother, at the very least. I have no idea what to say. Since this man does not listen to my remarks, it will have to be brief.
But again, we want no relationship with these people.
—No Contact Wanted
Dear No Contact: Ghosting a date is one thing, but ghosting your own brother?
Bottom line is that it’s not fair to cut him out without an explanation. Tell him the ways in which you feel hurt by his behavior. If he cares enough to listen, perhaps the two of you can visit a family therapist to get your relationship back on track. If he doesn’t, then your children are probably better off without the insults and intrusive questioning.
Dear Annie: My husband works in the family business alongside his father, his brother-in-law, and sometimes his brother and cousin. He is a generous, hardworking man who would give the shirt off his back for his family. Unfortunately, they seem to take advantage of that generosity.
Despite the pressures of the business, we make it a priority to enjoy our life together. On Sundays, we take our children out to eat, and we plan family activities and vacations with just the four of us. These outings are special to us and give our kids wonderful memories.
The problem is, his family makes us feel guilty for having these moments without them. They say things like, “You go out to eat every weekend,” as if it’s wrong that we don’t invite them along. Even their young children have been drawn into it, asking our kids where we went and saying, “I wish we could go, too.” It feels like they are using guilt and envy to undermine our choices.
The truth is, we live within our means. We pay our bills, budget carefully, and choose to spend what’s left on making memories with our kids. But the constant comments and guilt-tripping are starting to get under my husband’s skin, too.
I’ve kept quiet so far, but I’m wondering — what is the best way to respond when family tries to make us feel selfish or guilty for putting our little family first?
— Frustrated but Firm
Dear Frustrated but Firm: Stop feeling guilty for living your life. Parents are entitled to private family time without the whole clan tagging along. The next time someone complains, smile and say: “We like to keep Sundays just for us.” Period. No excuses, no guilt.
If they keep pushing, that’s their problem, not yours. You’re raising your kids, not running a restaurant.
Dear Annie: I’ve been married for 16 years, and lately, I’m not sure I want to stay in this marriage. I’ve always been the steady one—the saver, the planner, the person who makes sure the bills get paid and there’s something set aside for the future. My wife, on the other hand, has always been more impulsive when it comes to money. Over the years, I’ve watched her overspend and splurge without much thought, but I tried to keep things balanced.
She works as a nurse, and I’ve handled most of the financial responsibilities. Last year, I lost my job of seven years. Just two weeks later, she quit hers—something she has a pattern of doing during high-pressure times, like right before the holidays or big family trips. Facing a financial crunch, I reluctantly pulled from my retirement savings—money I had carefully put aside for our daughter’s college tuition and for a future rental property investment.
I used those funds only for essentials: mortgage payments, car repairs, and other immediate needs. I thought we were surviving. Then came the shock: my wife called and casually mentioned that she might’ve accidentally linked my credit card to her DoorDash account—and now it was declining purchases.
When I checked, I discovered she had racked up nearly $20,000 in charges in just 11 months. Not just on food, but also health and beauty products, random Amazon orders, and other retailers. She promised to pay it back, but the damage was done. That account was supposed to help secure our family’s future.
I feel betrayed—not just financially, but emotionally. Her spending feels selfish and out of touch with the reality we’re facing. Now I’m struggling to figure out how we’ll pay for our daughter’s tuition or afford the down payment on the property we’ve been eyeing for months. I’m heartbroken, angry, and unsure if this marriage is something I can or should continue.
Is this financial infidelity grounds for ending a marriage? Or am I being too rigid and unyielding?
—Feeling Used and Uncertain
Dear Used and Uncertain:
You’re not being too rigid. You’re someone who has worked hard, planned ahead, and done your best to care for your family—and now you’re wondering how things got so off track.
What your wife did isn’t a minor slip. Running up nearly $20,000 on your account, especially when you were trying to keep your family afloat, shows a troubling lack of communication and accountability. And the timing—quitting her job right after you lost yours—is more than a coincidence. It’s a pattern.
Marriage requires teamwork. If one person is constantly saving while the other is spending recklessly, resentment will build—and it sounds like you’re already there. This may not be about money alone; it’s about trust and whether or not it can be rebuilt.
Before making any final decisions, consider talking with a financial adviser and a counselor. See if your wife is willing to make changes and take real responsibility. If not, you have every right to protect your future and your daughter’s well-being—even if that means walking away.
You’ve given a lot. Now it’s time to decide what’s healthiest for you.
Dear Annie: I am at my wits’ end. I don’t know what to do for my 29-year-old grandson. He needs help, but I don’t know how to help him.
This is what I call a wasted life. He has no motivation to better himself. He has been living at my house for five months. After he got here, he got fired, so he sat here until the end of July doing nothing but sitting in his room playing video games. He sleeps all day, gets up at 5 or 6 p.m. and sits in the garage all night smoking pot.
I finally told him to get a job or move out. He got a super great job but slacks off constantly. He’s going to get fired soon, I know it. He has no money, no health insurance. I’ve tried to get him to go to counseling. I even gave him the number for a counseling group that charges based on your income. I did everything but dial the number, but he won’t do that. I’ve called his dad the last two times he missed work, but I’m not going to do that anymore. Like his dad said, he’s an adult. What can we do?
Today, he stayed up all night and finally went to bed at 11 a.m. He’s supposed to be at work at 1:30. He hates working. He loves acting and has been on a few shows and movies. He seems to have given that up. He also wrote a really great book. The story was good; he asked me to edit it, so I got to read it. His computer was stolen, and he gave up. I’m going to put him out of the house. I don’t know what to do with a wasted life. Any suggestions?
—Need Help
Dear Need Help: You said it yourself, and so did his father: He’s an adult. Adults don’t get to live rent-free, blow off work and smoke pot in the garage all night. He needs an ultimatum: Either get a job, pay rent and quit smoking — or move out.
It might seem harsh, but this is the only way he will learn real responsibility.
The bright side is that he seems to have wonderful interests and hobbies — when he takes the time to pursue them. Encourage him to continue acting and writing once he has a day job that allows him to pay the bills.
It sounds like you are very close to your grandson, and the fact that he asked you to edit his books means he respects you and values your opinion. The kindest thing you can do is to encourage him to make something of his life — and stop enabling his self-destructive lifestyle.
Dear Annie: I am 36 years old, and I recently spoke to my dad. He raised me, and we have always been like best friends until I moved to Virginia, just because of the distance.
I have an older sister who lives at home and doesn’t care to work, and my dad basically raises her son. I told my dad my future ambitions to adopt a child, and his response was so incredibly negative.
I asked him why he treats me so harshly, and he said, “Because you’re the only daughter I have left to do something good with her life.”
I understand where he’s coming from, but I don’t want the things that he wants for me. I’m grown, pay my bills, have made it through school and have gotten married. How do I proceed respectfully? His opinion is important but to what degree? Annie, your opinions are always honest. Please help.
— Upset Daughter
Dear Upset Daughter: Your dad’s words come from his love for you, but they are also hurtful and dismissive of your independence.
Next time he insults one of your choices, tell him that you appreciate his concern and take his opinion seriously. Then explain that you have your own goals, and you’re not looking for feedback. He can either support them or he can opt out of the conversation.
While it’s understandable to want his blessing, you also need to realize that you don’t need your father’s approval to pursue your dreams.
Dear Annie: My stepson is 22 and autistic. For 12 years, he lived with us half the time and with his mother the other half. During those years, I was very involved in his life—I went into his classroom to help with his needs, drove him to school and appointments, took him shopping and spent time just hanging out with him. I truly tried to be a loving, steady parental figure.
As he got older and bigger, things changed. He became more volatile. He has put holes in walls, broken furniture and been physically violent toward my husband. Three years ago, he threatened me directly, and before that he stalked one of my daughters online. My children and I are genuinely afraid of him.
At that point, I told my husband he had one year to find other living arrangements for his son because I no longer felt safe in my own home. My husband did so, but he has never stopped hoping his son could “come back” into the fold. He believes his son has made progress and deserves redemption.
My stepson has been in and out of therapy. My husband and I do couples therapy and individual therapy, but family therapy with my stepson ended when he said I could not be included because I am “not his mom.” I have now had minimal contact with him for a couple of years, and although I feel guilty, I also feel a huge weight off my shoulders.
Now my husband has asked if his son can join us for Thanksgiving with my large extended family—including my grandchildren and my brothers’ young children. I told him that if his son is there, my children and I will not attend. I said that if we had consistent family therapy with my stepson over a couple of years and I saw real change, I might reconsider. But right now, my fear is greater than my compassion.
I see how much it hurts my husband that his son is essentially being shunned, and I do not want to add to his pain. At the same time, I feel responsible for protecting my kids, my grandkids and my own sanity.
How can I maintain my boundaries and sense of safety while still being a supportive spouse? Am I being selfish or cautious with good reason?
—Protecting My Peace
Dear Protecting My Peace: You are not selfish. You are frightened, exhausted and trying to keep the people you love safe. Given your stepson’s past threats, stalking and violence, it is entirely reasonable to say, “I cannot have him at a big family gathering right now.”
Your compassion for him is clear: You showed up for him for years, in classrooms, cars and appointments. Wanting distance now does not erase that love. It means you finally listened to your own limits.
Your husband is grieving and hoping for a miracle. Let him know, gently: “I support you having a relationship with your son. I just cannot be part of holidays or close contact with him until there has been real, sustained change—and good therapy—over time.”
This is not a punishment. It is a boundary. And boundaries are how people with long, painful histories keep going without breaking.
“How Can I Forgive My Cheating Partner?” is out now! Annie Lane’s second anthology — featuring favorite columns on marriage, infidelity, communication and reconciliation — is available as a paperback and e-book. Visit http://www.creatorspublishing.com for more information. Send your questions for Annie Lane to dearannie@creators.com.
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