Dear Prudence,

I’m in a pickle, or rather my son is. He is 17, is about to graduate high school, and likes to smoke pot, which is illegal in my state. He has been through a teen-intervention course for having pot and paraphernalia in his vehicle (teen court, tour of the jail, the works), and we thought that would scare him, but once he met his community service requirements, he started smoking again. This past December, between his work and holiday money, he spent about $500 on pot. He wants to move out and live on his own when he is 18—he says his goals are to just “work and smoke pot.”

We have a college fund for him and are paying for his car. He can’t afford to take over car payments or get a loan. I refuse to have him drive a car that is in my name when he has been smoking. So we’re considering cashing in the college fund so he can pay off his car and get started. On the one hand, he can figure out how to pay for college himself—lots of kids do! On the other hand, I feel like a crap parent for making it hard on him, and I don’t want illegal drugs in my home. My question is this: Do I accept the decision of a 17-year-old who is pretty mature and competent, or give it more time and hope for a change? We’re getting close to when he wants to move out, and I really don’t want the liability of a car in my name being driven around by him or his friends with pot or paraphernalia in it.

—Hard Line?

If you set aside the money for college, it’s perfectly reasonable to leave it as is unless and until he decides to attend. If your son wants to move out and work and smoke pot—which, as goals go, is probably achievable—he can do so, but that doesn’t mean you have to buy him a car in order to facilitate that dream. If he can “figure out how to pay for college,” then he can figure out how to buy a car, or briefly stop dropping $500 a month on weed (!!) to save up for an apartment to smoke weed in. I think the better option is to figure out how you’re going to stop paying your son’s expenses once he turns 18 and set up a clear plan for turning over financial obligations like car payments. If he later decides he wants to try college, the money will still be there—you’re not taking anything away from him or trying to stop him from working instead. The struggle for you, I think, will be to let your son make his own decisions without trying to either shield him from consequences or steer him into choosing what you want for him.

Dear Prudence,

I’m mentoring a passionate young woman who is studying to enter my career field. She’s confronting some major issues in the process, mostly related to focus, money, and inconsistent support from her husband. I’ve seen this building for months. The advice I think I need to give her is that she has to have a serious conversation with her husband about his inconsistent support and ultimately decide how to proceed if he’s unable to commit. My belief is that the money and focus issues are secondary for her and will become manageable once her husband steps up to support her. My fear is that he’s not sufficiently mature or emotionally ready to commit to supporting her through the process of entering this profession. I don’t know how to tell her this, or even if I should. Maybe I can help guide her to figuring it out for herself. You’re a professional advice giver. Have any advice on how to give advice?

—How Much to Say

Oh boy, do I ever. Do not say any of these things to her! I think you have shot straight past “mentoring” and deep into the weeds of “interfering and overidentification.” Your role as a mentor is to offer her professional guidance and support—things like “Company X is hiring,” or “Let me put you in touch with Manager Y, who’s a subject-matter expert”—or to share your own work experience, not to tell her, “Your marriage is holding you back from professional success and you need to offer your husband an ultimatum.” No good can come from getting in the middle of her marriage. Part of being a good mentor is establishing and modeling appropriate boundaries and limits. I can understand the temptation to see yourself in a younger woman just starting out in your field and the desire to offer advice on every aspect of her life, not just on what questions to ask in job interviews or how to tailor a résumé. But you’re not her therapist or her life coach or even her friend. It’s her job to manage her personal finances and her relationship with her husband. It’s your job to offer career-specific and relevant advice. Don’t try to refurbish her whole life. You’ve got your own job to focus on.

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Dear Prudence,

I work in child care and have some issues with anxiety. I recently took a new job despite being five weeks pregnant, because my old job was horribly stressful and I knew I couldn’t last two more weeks there, let alone until I could start maternity leave. I did not tell my new boss that I was pregnant, and now that I’m eight weeks along, I feel like I should tell her. I feel guilty for “tricking” them into hiring someone who’s going to disappear for a couple of months within the first year. Every time I imagine the conversation I’ll have to have with my boss, it ends with me sobbing and apologizing, and her berating me and saying she wished she had never hired me.

To complicate matters, the section I work in has three people, one of whom is 15 weeks pregnant. I have had very few symptoms at this point, so it hasn’t affected my work, but I’m mainly concerned because of the eventual 18 weeks of maternity leave I will be taking at the end of August. I definitely want to come back to this job, though maybe not full time. Please help me with a script that helps me accept the right amount of blame without prostrating myself for something that would’ve happened sooner or later anyway. Legally I don’t have to tell an employer until 10 weeks before my maternity leave is due to start. Morally, though, I’m hoping you can help me.

—How to Tell My New Boss I’m Pregnant

Morally you are entirely in the clear. I am so sorry that you have pictured your boss berating you to the point of tears for doing something as normal as getting pregnant. Employees have been getting pregnant and taking time off to give birth for as long as people have been both (1) getting pregnant and (2) working, so, a pretty long time. It’s common. It’s expected. There are systems and workarounds in place to accommodate this. Not as many as there should be (that’s a topic for another column), but I promise you, you will not be the first employee to ask for maternity leave from this employer, or even this boss! You have not “tricked” anyone into anything.

The script I have for you, I’m afraid, will help you accept zero amount of blame, because you have done nothing blameworthy. You didn’t do something legally acceptable but morally ambiguous. You got pregnant. Your life is going to change in numerous ways, some of which will affect the way you work in both the short and long term, but you’re not dropping off the face of the Earth and retreating to Mom Island.

Do not apologize to your manager, and do not broach the subject as if you are bringing her bad news. You don’t have to tell her now, or even soon, since you’re so early on; ten weeks is plenty of time to start making alternate arrangements for project management. When you do tell her that you’re expecting, accept her congratulations and come up with a plan for offloading your work while you’re out. As for possibly moving from full time to part time after your maternity leave is over, I suggest you wait and see how things shake out first and have that conversation later. Good luck, and congratulations!

Dear Prudence,

For my entire adult life, I’ve identified as a lesbian. But a few months ago, I met a guy at an LGBTQ volunteer event. I mentioned I was a lesbian, and he told me he was queer. We immediately hit it off, and we’ve been hanging out regularly ever since. We’re both very shy—I rarely open up to people the way I have with him, and he’s said the same. I have lots of gay male friends, but this feels different. I’ve thought about it a lot, for a while now, and I’ve come to realize I have romantic feelings for him.

I have no idea what to do. There hasn’t been some broader realization that I’m attracted to men—just him. Is there some easy way to broach any of this with him? Should I just sit on these feelings and be sad about them until they pass?

—LGBTQWTF

You can definitely sit on these feelings, experience sadness, and wait for them to pass. That is a viable option! There’s nothing wrong with being sad, and there’s nothing wrong with putting romantic feelings to the side in order to preserve and prioritize a friendship. But if you think there’s a good chance he might return your romantic feelings, and you want to talk to him about it, then you absolutely can. There’s never a completely easy and risk-free way to tell a friend you’d like to date them, but I think honesty is the best policy here. “I’ve loved getting to know you, and I feel like we have a connection I don’t experience often. I’ve been a little surprised by these feelings, since I haven’t experienced this with a guy before, but I’m really into you, and I’d love to go out sometime. Would you be interested?” Follow up with the usual caveat that if he doesn’t feel the same way, that’s OK too, and that you still value and enjoy his friendship.

More Dear Prudence

Bitter and Trying: Prudie advises a letter writer who feels anger toward other parents after her own fertility struggles.

Grieving From the Outside: Prudie counsels a letter writer who’s devastated by the loss of a therapist.

University of Love: I’m crushing on my college teacher. Should I tell him?

Dear Prudence,

I’m in my late 20s and have been friends with my neighbor “Viv,” who’s 90, for almost six years. Viv lost her husband more than 10 years ago and lives alone. I come to visit with her about once a week as I work full time and go to school. Since she stopped driving a few years ago Viv tells me that her daughter and son-in-law (who live in our town) make a big deal out of taking her on simple errands and only contact her when they need something from her basement, which they use for storage. They also go on monthlong vacations and leave her to figure out taxi rides for appointments. She often worries that she’ll fall while she is home and that no one will find her for days. Her son who lives across the country brings up assisted living facilities each time he visits, as he is worried that she spends so much time alone. He says when she is ready he’ll come to make sure she gets settled and will take care of her house.

Last night when I visited, Viv told me again of her worries about being alone and said she would rather “go to sleep and not wake up” than deal with moving out of her beloved home of 65 years. What do I do? I love my friend and can understand that after 90 years of life, it can feel like a huge burden to go into assisted living and give up her independence. I do not believe she would intentionally harm herself, but I worry about the pain these feelings and loneliness cause her.

—Concerned Neighbor

It can be so difficult to find a way to respond to someone else’s grief and anguish without either over- or under-reacting. Her frustration, isolation, and sense that she’s slowly ceding control over aspects of her life are an understandable reaction to the indignities of aging, especially in a society that does not often value the needs and feelings of 90-year-olds. I’m glad she has someone she can speak honestly with about this, even if you’re only able to see her once a week. Those visits probably mean a lot to her. I think the next time you speak with her, you should address what she said specifically, if only to let her know that you’re here to listen and won’t try to push her into being happy about the prospect of a move to assisted living. “I just want to acknowledge what you said the last time we spoke, about how you’d rather die in your sleep than go to assisted living. I’m glad you could be honest with me, but I’m so sorry you’re feeling overwhelmed and anxious about the future. If you ever want to talk about your feelings, or what you fear about assisted living, or anything else, I’m here to listen.”

Dear Prudence,

In an effort to downsize, my grandparents put our family’s lake house on the market. My husband and I bought the property, with some help from my parents. No one else in the family expressed any interest. Now that we have moved in and remodeled, my aunt has announced she and her five kids are coming to stay with us this July! I told her that wouldn’t be possible, since we will be out of the country. She said she didn’t mind and would just “make herself at home.” She was furious when I told her no. Suddenly, I have “stolen” the family lake house and am “ungrateful” to my family. She even complained to my retired grandparents. I am happy to host my family—but only on my schedule. This is my home now and not a family vacation house anymore. We are paying a mortgage, for crying out loud. How do I hold my ground without destroying my family? My mother has already had a few screaming fits at my aunt.

—Lake House

Good news: You have already held your ground! There is not much more you need to do, given that you have established a clear limit and did not cave after your aunt threw a tantrum. Even better news: You have not destroyed your family; you have merely bought a home! You did not buy this home in secret before anyone else in the family had the opportunity to make an offer. You did not prevent your aunt from taking a vacation somewhere else. You did not even tell her she couldn’t use this home. You simply told her that she would have to coordinate with you first and schedule her travel for a time when you would be in town. Were she to call the police to report a theft, and try to file a report based on the circumstances you’ve described, no arrests would be made.

Your aunt is being wildly unreasonable, which is a hassle for you (and, it sounds like, your mother), but it does not necessarily follow that you have to do anything to manage her reaction. You can continue to be polite and friendly, and refuse to match her outburst with one of your own, but you have not harmed her in any way. You do not have to manage your aunt’s relationship with your mother. The fact that your home is the shiny toy your aunt is throwing a tantrum over doesn’t mean that she’s your responsibility. Stay as calm as possible, remind her that she’s welcome to schedule a visit for when you’re in town (unless you’ve decided that at this point you’d rather not host her at all, and frankly I wouldn’t blame you), and then refuse to discuss the subject any further.

﻿There’s more

“You can’t say ‘Make yourself at home’ TO YOURSELF! Someone else has to say that to you!”

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