My mother-in-law yells and cries if we don’t regularly give her money, and more advice from Dear Prudie.

Jenée Desmond-Harris is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat.

Q. Stressed mama: Do we have ethical obligations to help our in-laws? For the past five years, I have been the only income-earner while my husband is in school; he is now in year two of med school. We’re expecting our first child this fall. His parents ask for money regularly and have been borrowing our second car for the past eight months. We need it back soon. I can’t afford to get another car!

My mother-in-law has never thanked me once for being the breadwinner for years and footing the bill every time we help. My husband and I love each other dearly and have a great relationship otherwise, but the stress is taking a significant toll. My husband understands how I feel but cannot live with the guilt of not helping. My mother in-law will yell, cry, and stop talking to him for weeks when he calls her out. They badger him to use his student loan money. I feel they are emotionally manipulating him and it will only get worse the second he actually gets a job. I supported my husband in school wanting to support his dreams and thinking we would both benefit. That seems like a sad pipe dream now.

A: I don’t know about an ethical obligation, or even if that’s the right question. The extent to which supporting in-laws is a thing varies based on culture, class, individual relationships, personalities, and preferences. It’s also normal to do nothing, to have your in-laws support you, or to make great sacrifices to care for them.

The question is: What can you and your husband agree on? Ideally this would have happened before getting married, but that doesn’t mean you can’t work something out now. What can you both feel good about in terms of dollars per month and time with the car? Or, where can you find compromise between what each of you would feel good about? If you really don’t want to give anything or if he refuses to agree to any plan other than “What my mom wants, my mom gets,” your marriage may be in trouble. But hopefully there’s some middle ground. I know money is tight but if at all possible, a marriage counselor might be able to help you find it. I would suggest setting a budget for now, while the two of you aren’t bringing in much money, and reevaluating when your husband is done with school and residency and is making a higher income.

How to Get Advice From Prudie:

• Send questions for publication here. (Questions may be edited.)

• Join the live chat Mondays at noon. Submit your questions and comments here before or during the discussion.

Q. Just want us to be happy: I’ve been married to my husband for nearly five years, and he’s been a really good partner. He’s thoughtful and kind, is a good roommate, takes on his share of cooking/domestic work, supportive when I’m anxious or down, and we have the same values and goals for the future.

He’s always had an adventurous sense of style, and will cross gender lines to find patterns and fits he likes and that make him feel comfortable. However, since he’s been vaccinated and it’s felt safe to try clothes on at thrift stores, he has solely been getting women’s clothes. He’ll leave the house to go through a different women’s section. He’s found women’s shorts, pants, sleeveless tops, and blouses. Recently he came back with a dress. I asked about why he’s been so interested in women’s clothes recently, and he said he’s just been tired of the limited cuts and fits men’s clothing offers, and asked if I had feelings about that.

I let him know that I love that he’s exploring and finding things he’s comfortable and happy in, but also I’ve also been a little stressed by it for a few reasons. He’s a bit of a perfectionist and when he is unsure about his outfit, he’ll ask me to help him fix it, and then going back and forth on his options, making us late on more than a few occasions. Sometimes, these pieces are difficult to style with the rest of his wardrobe.

But also, his choices have meant my own style has gotten less adventurous because I no longer have the benefit of being accompanied by a masculine partner. There have been occasions like date nights where I’ll put on a daring and flirtatious outfit, and look over to see him in a crop top, and I’ll have to change into something more conservative because as a femme, street harassment is (and has been) targeted at me when I’m dressed up and he doesn’t present as masculine (“you need to find a real man”/“I could treat you right” and the like). I don’t mind that he’s expanding his wardrobe and expression, but I want him to be aware that the way he dresses does affect me in the choices I make with regards to safety in public.

He was pretty quiet, and seemed upset a few days later in a different conversation by the idea that the way he dresses affects how safe I feel. Am I being unfair, or overcautious? I’m bisexual, and have no problem if he decides to present any way he likes, but I also want to be honest especially since he’s a white guy, and hasn’t had to worry about the way he’s perceived much, and I don’t want to be gauging or managing that alone as a Black woman. I want him to feel safe with me, and for him to feel free to evolve as he grows in his understanding of himself, but I don’t want to be styling him in the morning in pieces I’m not comfortable with, and to later respond to strangers’ questions and harassment in the evening. Am I doing something wrong?

A: I don’t think you’re doing anything wrong exactly. In fact, I think your marriage seems wonderfully supportive and open.

But you could think about this situation differently. Yes, you’re losing the benefit of a masculine-presenting companion and what that means for the amount of street harassment you get, and that’s worth mourning. But by being frustrated with your husband instead of the people doing the harassment and the society that lets it exist, you’re missing the mark a bit. He’s not obligated to dress to minimize street harassment (which, by the way, happens to people wearing sleeping-bag coats in the winter all the time, so you can really only control so much with clothing) any more than you are. You two should take measures to make yourselves more comfortable just like you would if you were out with a female friend and you both wanted to wear crop tops. Of course you really shouldn’t have to, but if using ride share instead of walking, or wearing headphones and sunglasses to block things out, or carrying mace if it’s legal where you live makes you feel more secure—do that instead of guilting your husband about what he wants to put on.

Q. Distant auntie: About a year ago, I ended my relationship with my brother “Greg” and his wife “Kelly.” Their racism, cruel treatment of animals, manipulation of our parents, and frankly bizarre theories about COVID and vaccination just became too much for me. I’m truly happy with my decision to end it, and our parents are understanding of my choice. They still keep in contact with Greg and Kelly, and I’m comfortable with that.

Recently Greg and Kelly had their first child. Technically I am the child’s aunt, and my parents have been hinting that they’d like me to reconnect with Greg and Kelly so I can be a part of the baby’s life and he can grow up with an auntie. But Prudence, I’m not so sure I want to. Right now the baby is a literal baby—I can’t independently have a relationship with him, and I don’t want to have a relationship with his parents. I thought about sending gifts for him at Christmas and on birthdays, but Greg and Kelly have entire rooms in their house piled high with more things than a dozen babies could ever hope to use. I have no doubt that anything I sent would just be added to the piles and not used. Additionally, in a year or so, a work contract will take me overseas for a few years, so I sadly won’t be around to spend time with the baby even if the opportunity did present itself (if my parents were babysitting and I dropped by, for example).

My thinking is that instead of working to be a presence in the baby’s life, I’ll add a hundred dollars or so to an investment for the baby every year—the same amount I would have spent on a gift. (I plan on doing the same thing for any other children Greg and Kelly have, to keep things fair.) Once the child turns 18, I would like to give him the money I’ve kept aside for him to spend as he wishes. He’ll be an adult by then, so he can decide for himself if he wants to connect with me or if he just wants to take the money and go. I’m comfortable with this, but my parents are saying it’s cold and that I’ll regret not being a part of the baby’s life. Honestly, Prudence, at this point my only regret is not ending my relationship with Greg and Kelly sooner. What should I do?

A: This plan is perfect. It would be tough to develop a close relationship with a child if you don’t see eye to eye with their parents on anything. And it would be stressful for everyone involved (plus, potentially traumatizing for the kid if you did manage to become close and then had a huge falling out and disappeared). Hopefully when he’s older, he’ll appreciate having a different kind of adult in his life. 

Q. Bullies and dragons: I work with a small team of health care professionals, in a clinic at a large health care organization. One of our co-workers, “Gia,” spends quite a bit of time during work hours on her other business (we are paid by the hour, so at best it’s disingenuous and at worst, it’s fraudulent). Gia is also super prickly, defensive, and judgmental of everyone else. The only co-worker who gets along with her is “Sue,” who also works in the same side business (and spends work time doing it as well), but Sue isn’t a bully like Gia.

No one on the team wants to speak to a manager about the issues (or even report it anonymously), as we work in incredibly close quarters and the atmosphere is close to intolerable when the two are here as it is. If it’s reported, our fear is that nothing will happen and the bully will become a dragon. I also feel urpy about being a tattletale. Could surely use your advice on what to do …

A: Gia’s work on her other business isn’t your problem. If I were you, I’d just forget about that. If she’s getting away with it, good for her. If she eventually gets caught, that’s her problem. If her slacking is somehow increasing your workload, complain about what’s on your plate and let the higher-ups put the pieces together.

Now, if her behavior really rises to the level of bullying, especially if it’s making it hard for you to do your job, definitely bring that up with a supervisor or with HR. But “prickly, defensive, and judgmental” doesn’t exactly sound reportable—it just sounds like a bad personality. Which many people’s co-workers have. If it’s just that you don’t like her, that’s totally fair, but there’s not necessarily anything you can do about it except to limit your interactions with her or look for a new job.

Q. Can’t I just have a date: I haven’t dated in 10 years for … reasons. I’m in my mid-30s, my friends are in their mid-30s, and they constantly text me about their partners (long-term or not long-term or lack thereof). I try to be very supportive, but it seems that when I try to have a conversation about my own potential relationship(s), they bail. I’m just now starting to date again, and just now starting to have a relationship. Their lack of interest is really hurtful to me and it makes me feel like an emotional crutch. It feels to me that they don’t actually care about my own romantic developments.

A: This is odd. Most friends love to hear about other friends’ dating adventures. Could it be that they’re trying not to show too much excitement or pushiness since this is such new territory for you and they don’t want you to feel overwhelmed? Is there something troubling about the way you’re being treated that might make them feel uncomfortable being supportive? Are your updates short on details and lacking requests for feedback? Do you have a history of being sensitive that would make them cautious about sharing their thoughts?

Of course, it’s possible that they’re just selfish. But I doubt it! Why don’t you frame your next update as a question they can answer? “What kind of birthday gift is good for four months of dating?” or “Do you think I should leave a toothbrush at his house?” “How did you feel after your first sleepover?” or ask for feedback on how things are moving along. And if you still don’t get any good replies, ask them explicitly what’s going on.

Q. Re: Stressed mama: Your doctor-to-be will have at least three years of postgrad training after med school, and the pay’s not great. You’ll have enough for yourselves and maybe a baby in that time, but his student loans will be coming due by then. Take it from one who knows—you won’t have a lot of extra money sitting around for the next 10 years, longer if he picks a specialty that requires additional years of training.

A: Whew. I’d forgotten about the student loans. Well, if you literally don’t have the money, this problem might solve itself!

Q. Re: Distant aunt: I would amend your plan to also include a short heartfelt card on each occasion. No need to explain why you haven’t been around (particularly if you plan on living overseas)—just that you love them, are thinking of them, and wish them well. Kids don’t pay that much attention to cards, but at least that way, when you appear on their 18^th birthday with a sack o’ cash, they’ll probably remember your name.

A: Yes! Great idea. 

Jenée Desmond-Harris: With that, I’m signing off. Thanks for the questions, and thanks to everyone who weighed in. Talk to you next week!