Dear Prudence

Help! I Can’t Believe My Boyfriend Is Just Letting Himself Go Bald.

Read what Prudie had to say in Part 2 of this week’s live chat.

The back of a man's head who is experiencing balding. An illustrated broken heart is overlaid behind him.
Photo illustration by Slate. Photo by Getty Images Plus.

Dear Prudence is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat. (R. Eric Thomas is filling in as Prudie for Jenée Desmond-Harris while she’s on parental leave.)

Q. Hairbrained Idea: My loving, wonderful boyfriend (he is in his late 20s) is dealing with a receding hairline. He remarks on this every so often with some displeasure but seems more or less resigned to it (as far as I know). Once or twice, he has brought up treatments that are available for this issue, of which I know little about. Once, he even vaguely asked me if I thought it was a good idea to go on them. I gave him the supportive “if that would make you feel better, sure” answer. The thing is, I really don’t want him to lose all his hair. I know it’s inevitable, but we’re still pretty young, and I like his hair as it is now—perhaps selfishly. He’s a pretty laid-back guy, and I know that if I encouraged him he would be much more likely to explore his options. But I would hate for him to think I’m superficial or that I would like him less if he was balding. On the other hand, I thoroughly invest in my appearance and actively work to prepare my skin/body for the inevitable effects of aging, so would it really be so crazy for him to do so too. Would it be cruel of me to gently encourage him to explore his options? Wait to see if he brings it up again? Or should I get over this and let nature take its course, even if it means I’ll be less attracted to him?

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A. Since he seems to share your concern about his hairline, it makes sense for you to encourage him to seek out treatment options when he brings it up again. Doing so out of the blue might get in his head a little, no pun intended, so you’re probably best letting him start the conversation. It sounds like he’s looking for your support or reassurance, so you should try to determine whether he’s trying to get you to tell him you’ll love him no matter what or trying to get your opinion about hair replacement before plunging in.

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.

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Q. Supportive But Restless: I’m struggling. My brother-in-law moved in with my wife and I several months ago. He’s in between jobs and struggling to find his path. I was fully supportive of the time. That was many months ago and…well…there’s no sign of him leaving.

I love my brother-in-law. But I also love my space. I relished time with my kids, wife, and I and to some extent…struggle sharing it. Meanwhile, my brother-in-law seems to have given up on any kind of job search. He spends no time doing anything to change his situation. He may be depressed. While I’ve hinted to my wife that I’m getting sour on the situation, there has been no movement. I’m unsure how to handle this situation in a way that’s loving to my wife and brother-in-law but also changes the status quo.

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A. You’ll need to do more than drop hints. You and your wife should sit down and have a conversation about what your household needs are and what your capacity for helping your brother-in-law is. Find out what she values most here—giving her brother space, helping him get back on his feet, household peace, or something else. And share what you value most. Ask yourselves if you’re actually helping your brother-in-law in the most effective way. Once you’re both on the same page, or close to the same page, have a similar conversation with your brother-in-law about what he needs and what everyone’s capacity is.

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Q. Can’t Communicate: I have a younger sister (8 years apart) whom we can’t handle anymore. We’ve clearly done something wrong since she is riddled with cynicism towards us. She uses her mental illness to get everything her way or no way. I can swear on my life we never abused her, but we’ve apologized for any hurt we might’ve caused without knowing.

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Due to complicated family/job circumstances, we will all be relocating elsewhere next year after she turns 18. She does not wish to leave, which is understandable. The plan is for her to live with her boyfriend, which his parents have agreed to. She doesn’t want to live with me because “she’s tired of dealing with our shit.” Our parents will send her money each month until she can be independent, but she has been bringing up driving lessons (that are $2,000, which we’re willing to pay), a new car, and an extra $800 allowance per month. That is not something we can afford!

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When we say no to her (on anything), she starts spewing off about how her struggles (that she is seeking professional help for) are all our fault and she will be more depressed now. She even quit school because she feels that going to school is too stressful. How do we stop her from holding her struggles over our heads? My mom feels bad when she brings it up and just lets her have everything her way, even if it’s sabotaging her own future. At this rate, she won’t even have a high school diploma.

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A. It will be useful for your family to go through some counseling sessions together before entering into this new financial arrangement, which seems like it will only further complicate a hard situation. Your sister’s therapy will, hopefully, help ease some of the pain she’s experiencing, but there’s clearly something broken in the family unit that also needs addressing. Right now, it seems like all of the problems are being surfaced your sister, which isn’t a stance that’s going to help any of you to move forward.

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Q. The Office Snitch: I’m a manager of a pretty dysfunctional team. So dysfunctional that my manager encouraged me to take a yearlong secondment managing a different team so I could have a reprieve from the toxic behavior of one team member in particular. The person filling in for me has been trying some team-building activities lately and while I’m not convinced it’s possible to turn this team around, I have admired their efforts in trying. That is, until I watched a Zoom recording of a recent team meeting.

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The meeting involved a team-building activity that was hijacked by the difficult team member. Among other things, they disparaged a fellow team member who has a disability and made some other insensitive remarks which made another team member leave the meeting in tears. The acting manager did nothing and in fact, made comments that appeared to condone this shocking behavior. I made inquiries as to whether or not the acting manager took action after the meeting to address the problem behavior with the individual—they didn’t. So, I showed my manager the recording, who was so outraged they took it to their manager, who was also furious about the incident and referred it to HR.

The problem is that HR has thrown their hands in the air saying the troublemaker can’t be seriously disciplined as the behavior occurred as part of a team-building activity. Not only has this person gotten away with some terrible behavior, but the acting manager has also frozen me out and made it clear that they want to minimize interacting with me. I feel as though it would have been smarter to have let the whole thing slide. I know I did the right thing reporting it but I can’t help feeling I’m a snitch. I also get the feeling that others in the company know what I did and that I can’t be trusted. Can I ride this out or should I start making plans to find another job?

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A. It sounds as if everyone with power in this situation dropped the ball except you, so I wouldn’t characterize this as snitching so much as you following an established procedure meant to maintain civility and prevent abuse. Anyone in the company who thinks you can’t be trusted is apparently unconcerned with the teammates that were maligned or the teammate who left the meeting in tears. So, I take a pretty dim view of their opinion.

You should ride this out if you feel that there are aspects of this job that you like or that the dysfunction of your team can be remedied. It sounds like the problems precede you and extend beyond your reach, so while you can ride out the mini-controversy, the better question is why should you? What is there to salvage here? The reasons for staying could be financial or other, but you should be clear with yourself about what you intend to accomplish going forward, knowing that the toxicity seems to be running amok.

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Q. The Monster of Christmas Present: I’m a woman in her early 20s who, last winter, accepted a vacation idea from a close friend of mine: We would spend this Christmas together in a resort park. An expensive choice for both of us but not beyond possibility. She experienced happy Christmases as a child, celebrating with a large extended family but those days are long gone and she now spends the season with her parents and brother. She, and her brother, still live with their parents but the family is incredibly dysfunctional. The atmosphere of the house is a daily struggle for her and she talks frequently about how she’ll raise her own family differently.

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Each year when Christmas comes around, I see her sadness for her family situation swing into depression. Aside from my friend, the rest of the family would prefer Christmas to pass as a non-event—no decorations, no time spent together, and no presents. The vacation seemed like a happy alternative but now, as her plans get more elaborate and expensive, I’m beginning to worry. The resort is paid for, and I’ve put money aside for restaurants and on-site activities. Yet every time she has a bad day it’s her favorite topic to come back to and she brings out her lists. We’re to have giant Santa sacks filled with presents, stockings, matching pajama sets, Christmas Eve night surprise boxes, themed craft and leisure activities, and gourmet snacks…

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Aside from the obvious pressure I feel to live up to the fantasy Christmas she’s creating day by day, there’s one other thing to know about my friend. She, and her family, are hoarders. Their home no longer has rooms; it has pathways. While I know she’s not entirely oblivious to the problem, she does have a lot of denial. She has so much stuff. Recently, I listened with horror as she casually mentioned how she felt some guilt over the fact that she had not moved most of her Christmas gifts from where she left them last December. I’m resentful of the prospect of spending my much-needed money on materialistic items that will end up on her floor.

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I tried to have a discussion about budgeting and expectations. Despite the fact that she can’t give a single gift idea because she already has everything she needs, she is adamant that she loves to receive presents and no Christmas or birthday is complete without them. And even if I stick to my personal budget, I’m worried I’ll look like the Grinch when the time comes while she’s spent without care. I thought the resort and company would be enough but it seems her perfect Christmas is a capitalist trap. She is really emotionally invested in this trip—how do I balance both of our expectations without turning it into a conflict?

A. You’re going to need to circle back to the conversation about budgeting and expectations and make very clear what’s possible for you. Even if she’s adamant about wanting more, you always have to stick to what the budget says. I suggest you come into the conversation with a price cap for all presents that both of you need to adhere to. Remind her that this is an experience you’re having together, so your needs also should be considered. If she’s truly stubborn about the sacks of presents, you can even suggest that she increase the present budget by putting more money in and you can buy her presents with that.

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I know her happiness is your concern here and you want to do something nice for someone you care about. But you’re going to end up resentful unless you establish firm guardrails now and don’t waiver. She may make you feel like a Grinch, but would a Grinch go all the way to a resort, buy her whatever item you decide to buy, and spend time with her? If she calls you a Grinch or something like it, push back kindly but firmly. This is something you’re doing together; you’re not her tour guide or her fairy godmother so you need to meet in the middle.

Q. Re: The Office Snitch: It depends on what was said, but HR should know that disability is a protected class and by not acting on it, they’re opening the company up to liability. No matter what, HR should be taking this seriously and the team-building bit is hogwash.

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A. Yes, this HR department is seriously lacking. Throw the whole company in the bin, honestly.

Q. Leaving?!: Eric, I just want to say that you’ve been an EXCELLENT Prudence. Best wishes on your next gig.

A. Thank you so much. I want to reiterate again how extraordinary this experience has been and how generous and wise this community of readers, commenters, and advice-givers has been. I really appreciate the warm welcome you all gave me. (Even the people who emailed me very forceful rebuttals to some of the advice I gave, lol.)

R. Eric Thomas: That’s all we have time for this week. Thanks for your questions and comments. Be good to yourselves!

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