Dear Prudence,

My husband had three grown children before I married him. His two sons are successful adults, while his daughter would rather do anything than work. She has three children and isn’t in touch with their fathers. We have paid for technical training, child care, and a car. My stepdaughter dropped out because the training was “too hard.” We arranged for jobs, and she didn’t bother to show up. We stopped giving her money after it became apparent all the “emergencies” were made up (give her rent money, and it would never be spent on rent). She and the kids live with her maternal grandmother. We visited last week and had an early Christmas. We made sure all the grandchildren had new shoes and winter coats, and we bought bikes for the older two boys. Only our oldest grandson let it slip when we called that as soon as we left, his mother stripped her children of all the gifts we gave them and tried to return them to the store for cash. She sold the bikes for a pittance online. My husband is furious, and I feel sick. We don’t know what to do, and every option is awful. If we confront my stepdaughter, she will throw a fit. Or she will take it out on the kids. Or cut us off from them entirely (she has done that to her brother and mother already). We love our grandchildren.

—Would-Be Givers

I’m assuming that when you say you worry your stepdaughter will “take it out on the kids,” you don’t mean you fear she’ll hurt or abuse them—namely, that you don’t think calling child protective services is a necessary or viable next step. If that’s the case, your goal is to continue to maximize the time you can spend with your grandchildren while minimizing the amount of money their mother can chisel out of any gifts you give them. You might store bigger presents like bikes at your house, so the kids can use them when they visit, and offer to take the kids off their mother’s hands as often as you possibly can. Try to give the kids gifts that can’t be resold or returned, such as taking them to the movies or paying for experiences.

I also don’t want to assume that you’ve completely ruled out CPS. If your stepdaughter steals Christmas presents and winter coats off her children’s backs and you’re worried she’d retaliate against your grandchildren if you made her angry, then I think there’s a chance she’s abusing the children in other ways. Try to keep as close an eye on them as possible, and consider seriously whether you and your husband might be able to help care for them if you felt like calling CPS was a necessary action. In the meantime, do whatever you can to make the kids feel special while also making it difficult for your stepdaughter to get cash out of you, either directly or indirectly.

Dear Prudence,

Last year, my sister-in-law lost her husband to suicide, leaving her and her two sons in serious debt. They live in an expensive community, and my sister-in-law only has a part-time job. My husband and I have stepped in and spent over $20,000 to help them, from paying for the funeral to paying the mortgage so they don’t lose the house. We have had to dip into our savings. We can’t keep this up, but my sister-in-law will not see reason. Her mother has offered up her home and even arranged a job. Selling the house and moving would put my sister-in-law in a stable financial position. My sister-in-law refuses to face reality. She will not discuss the situation and tells us it is “none of our concern,” then demands we pay her bills. I understand the desire to keep her home and the boys in their schools, but that is not possible. She can’t afford this lifestyle anymore, and she will lose the house without us. My own family is facing a medical crisis over my father’s dementia. My husband and I are losing money, losing sleep, and losing our patience. What should we do?

—Something Has to Give

I realize your sister-in-law has been still fairly recently bereaved, and I don’t mean to suggest you should just lightly cut her off as if she were a friend who’d borrowed McDonald’s money a few too many weeks in a row. But while this won’t be easy, your next job is at least simple: Stop giving her money. It’s especially simple because you don’t really have any more money. Just let her know as soon as you can that you can’t afford to make any more payments and that there’s nothing left you can give her.

Be kind but frank when you tell her there’s no more money. Don’t worry about persuading her to sell the house—the reality of her bank account will be more convincing than your words could ever be. You don’t have to then help her plan her next move. She’s made it clear she wants to figure that out on her own, and you know that at least one other person has offered her a job and a place to live. There are other people in her life who are willing and able to help her, and she has options that include downsizing without facing homelessness. But you and your husband are in crisis mode yourselves, and you need to be able to look after each other financially and emotionally right now. If she later decides she does need help downsizing and turns to you, you can try to help in more limited ways, such as helping her pack or taking the kids for a few hours while she signs papers with the lawyers. But you’ve done all you can financially, and it’ll be better for all of you if you tell her that today.

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Dear Prudence,

One of my best friends cannot have children. She and her husband spent years trying to conceive and only gave up after they’d spent all their money on fertility treatment. Obviously, it’s heartbreaking. I, on the other hand, had an unplanned pregnancy immediately after getting married. We were able to navigate that well; she demonstrated a lot of strength, and I tried hard to be conscientious. Shortly after she and her husband gave up for good, I had another unplanned pregnancy. Again, I tried hard to be sensitive, but now my baby is a month old, and I haven’t seen my friend since before I was pregnant. We’ve kept in touch via text and social media but rarely if ever talked about my children. When my baby was born, we had a medical emergency that meant he spent a week in the hospital. It was devastating and frightening, but my friend only sent one text and “liked” my social media updates.

Now that the crisis is over, and we’re settling into a normal daily life, I’m pretty upset at the distance my friend has maintained. I know I can’t actually understand the pain she’s been through, but I nearly lost my child and barely heard from her. I’ve really tried to be understanding, but I’m hurt. I didn’t want to let our differences in fertility come between us, but it feels like the friendship is over. If I were to talk to her about this, I’d want it to be face to face, but honestly I’m busy with two little kids now. After the way she’s blown us off, it doesn’t feel worth the effort to try to arrange a time to get together. Is this friendship over, or am I missing a sensitivity chip?

—Ready to Move On

I’m hesitant to be harsh toward your friend, who’s clearly in a lot of pain, but even if she didn’t feel able to be around children or pregnant women over the past year or so, she could have sent a note or some token that she was thinking of you when your baby was in the hospital. You’re not obligated to try to force this friendship back toward what it once was, but it might be worth giving her at least the opportunity to discuss the situation, even if it only means that you two part on better terms. It might be that the best possible outcome is to acknowledge that you’re both going your own ways in life while remembering fondly what you’ve meant to each other. It would be understandable if you simply took her cue and didn’t attempt to get in touch. You’re both hurt, and you’re busy, and that would be fine.

If you find yourself still dwelling on this, it might help to send a text or an email along these lines: “I was thinking of you the other day. I know how difficult the last few years have been for you, and I hope you’re taking care of yourself. Our friendship has changed lately, and I understand that, but it was really painful to go through that week in the hospital when we didn’t know if the baby was going to be OK and barely hear from you. It hurt me deeply.” But if the prospect of having this conversation anywhere but in person doesn’t appeal to you, you’re under no obligation to force a deeper conversation out of her.

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Dear Prudence,

I’ve had the same close friend group since high school. We are now all in our early 20s and in different stages in our lives. My friend “Alex” and I are working, going to school, and have driver’s licenses. The other three live with their parents, are working on their art, and don’t drive. Alex and I have happily helped out with lifts and paying for the bulk of our group activities since we were 16. Over the years I’ve always had a strained relationship with “Jane.” I feel like she only has time for me when she wants something. This semester, Jane, who’s never been to college, decided that she wanted to take a class with me at the community college where I take an extra class every semester.

So, without telling me, she signed up to join my class, then assumed that I would drive her. Because of where we’re both coming from, that means I don’t get home until 11:30 p.m., but I have to be up at 3 a.m. for work. I work full time and attend two schools. I finally told her that I couldn’t drive her anymore, as I just don’t have the time, but that I would drive her for another week so she had time to arrange for another ride. She told me that I was the most selfish person she knows, which is why everyone hates me, and that I just don’t want to see her succeed. At this point I really just want to be done with Jane. I think I deserve to be treated better than this. I’ve expressed this to the rest of my friends, and they all agree that Jane has acted badly, but they still invite her to everything. The group expectation is that I continue on the way I had been, including picking her up so she can participate. I feel like my options are business as usual or walk away from all of my friends. I know that at this age it’s normal to drift away from each other, but I’m scared to be alone, and I don’t make friends easily. Do I have any other options?

—Borderline Friendless

Walking away from someone who responds to “Sorry, I can’t drive you to class anymore after next week” with “You’re the most selfish person I know, everyone hates you, and you’re just a jealous hater” is the right move. The fact that you’ve put up with Jane for the last several years is a testament to your patience and (possibly overly) generous nature. The line you should draw with your other friends—who may be perfectly lovely people, if a bit conflict-avoidant—is, “Will I be expected to interact with or do favors for Jane?” If the answer is no, then don’t feel like you have to cut them all out of your life just because they’re willing to play doormat to her. If Alex wants to get lunch just the two of you and you’d like to go, do it. But if they invite you out to a group hang and ask if you can pick Jane up, turn them down.

If you’re not sure you can do that, and if you can’t really imagine yourself spending time with your mutual friends without also giving in to Jane’s demands, then it’s fine to take a break from the group itself, maybe even a permanent one. But since you’re anxious about the prospect of dropping everyone at once, it might help ease the transition if you keep a standing lunch date once a month or so with one or two other members of the old group. Lots of people your age are looking for new friends, and although your schedule’s already pretty packed, you’ll eventually find friends among your fellow students or co-workers—maybe even ones who have their own cars, too.

Dear Prudence Uncensored

“Knowing that your kids are thriving, while your friend has been unable to have any, that’s tough to talk about.”

Daniel Mallory Ortberg and Nicole Cliffe discuss a letter in this week’s Dear Prudence Uncensored—only for Slate Plus members.

Dear Prudence,

I’m a 28-year-old nonbinary person who was assigned male at birth. I’ve been blessed with kind and supportive friends and family, and with the help of a therapist, I started transitioning. At this point I get read as a cis woman in public, and I’m comfortable with that. I also feel happy with my body as it is. Unfortunately, dating can be really fraught. I always disclose that I’m nonbinary, but the guys who are interested in dating me either lose interest or uncomfortably fetishize me on the basis of whether I’ve had certain types of surgery. What can I do? I’ve been lucky to have good friends and family, but I can’t help but feel lonely.

—Lonely and Nonbinary

I don’t want to make a plug for it, exactly, because I don’t think of it as a tactic a person can deploy in order to avoid heartache, but I think dating other trans people can be a real relief if you’ve spent a lot of time trying to deal with cis people chasing, fetishizing, or objectifying you. That’s not to say that trans people are never capable of doing those things, but it’ll reduce that sort of thing considerably—and there’s the added bonus of shared experiences and the potential for profound solidarity. It’s a smaller dating pool, to be sure; there are a lot more cis people than trans (SO FAR), but I think having fewer dates is a decent trade-off if it also means dealing with fewer chasers and gawkers. And good luck!

Dear Prudence,

My significant other, myself, and her sister are planning a cross-country road trip for New Year’s. We’ve been planning it for about three months, and last week my SO’s sister asked that we make a detour to pick up her boyfriend. My SO and I don’t get along with him and generally disapprove of their relationship, but we acknowledge they’re together and we can’t do anything about it. This detour would add at least three hours to our already 22-hour drive, and will force us to take a worse route (hitting more cities and therefore more traffic) and to be stuck in a car with someone we don’t get along with after more than 15 hours of driving. It’s ridiculous, and we’re at a loss as to what to do.

—Directionless Driver

I really do sympathize, but I don’t think you can outright forbid your significant other’s sister from bringing her own boyfriend on a trip with the two of you, thus forcing her to be a third wheel. I get that he’s out of your way, but presumably if you liked him, you’d be willing to drive the three extra hours. It’s not “ridiculous” that she would like to bring her boyfriend on a trip with another couple, although it’s certainly undesirable. As long as he’s willing to pay his own way, I think the right thing to do is include him and be as polite as possible. If you don’t think you’re capable of politeness while trapped in a car with this guy, then you can suddenly remember conflicting plans that mean you’ll have to postpone this trip and hope that by the time your schedules all sync up this guy is ancient history, or you can be honest and tell her you can’t stand her boyfriend. Maybe say something more diplomatic than “we can’t stand your boyfriend.” At that point, though, you’ll probably be in a significant enough fight that taking a road trip together, with or without the boyfriend, will be out of the question.

You could also say that your limit of time in the car is around 22 hours, but you’d be happy to drop her off at a point on the pre-existing route, where her boyfriend could whisk her away for a little couples time while you and your significant other continue on your merry way, stopping for her sister at the same point on the drive back. If he’s willing to come pick her up, so much the better: You get to spend some time with the half of the couple you enjoy and some time just you and your partner. If he’s not, “maybe he can join us next year—we have so much time to plan between now and then.” Hopefully, of course, next year he’ll no longer be in the picture. If he is, you have a long time to think of an excuse.

Classic Prudie

“I’ve been overweight most of my life. I graduated from college morbidly obese, weighing over 300 pounds. I continued to gain and, at my heaviest, was 420 pounds. I finally hit rock bottom when I realized I had nothing in my life but food. I started to eat right and exercise. I got results and was encouraged by family and friends to get bariatric surgery. The surgery was a tremendous help, and I now weigh well within normal limits. My problem is that all my life I have told myself that once I lost weight things would get better for me. But I still have nobody special in my life. I have the same dead-end job I did when I was heavy. I don’t go skydiving or surfing or all the great things I thought I’d do once I wasn’t heavy any more. I’m waiting around for my new life to begin.”