Dear Prudence

Help! My Roommate’s Wealthy Parents Want to Pay Me to Stay Friends With Their Daughter.

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

Two young adult women wearing backpacks, backs turned to camera, separated by a stack of money.
Photo illustration by Slate. Photos by Thinkstock.

Mallory Ortberg is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat. 

Q. No strings: I am a struggling college student up to my ears in loans and am estranged from my family. (I am gay and an atheist; they are deeply Catholic.) I have roomed with “Natalie” since freshman year. Natalie has many mental issues. She is school-brilliant, but socially not so much. I spent a lot of my first two years with her, pulling her out of the dorm and into socializing. She has a private therapist and is doing much better, but she still relies on me for a lot. She will not go out if I am not there and has refused invitations to events if I am not invited. I was thinking of dropping out of school to work when Natalie’s parents approached me. They told me I was the best thing to happen to their daughter, and they were willing to fund my education if I stayed and “continued to be her friend.” They also don’t want Natalie to know.

I am very, very tempted to take the money. Natalie comes from serious, old-world money—like yearly vacations to the family home in the Alps kind of money. I also know it will kill Natalie to think her parents bought a friend for her. What should I do?

A: It sounds like you’ve been trying to disentangle your life, at least somewhat, from Natalie’s; accepting this offer, while certainly financially advantageous, would keep you from that goal in a pretty serious way. Not to mention the fact that it would require you to keep a sizable secret from your roommate and that you know she’d be devastated if she ever found out.

It may not be that your only two options are to either drop out or to take this offer. You’re at least halfway through your university education. It might help to speak to the financial aid office to get a sense of whether there are any other programs or assistance you can access in order to graduate.

That’s not to say you’re wrong to consider the offer! But consider the many ways in which it could go badly. What would you do if halfway through the next year Natalie learned about your financial arrangement with her family? Would you two be able to continue to live together? If not, would you have any guarantee that her family would continue to pay for your education? What if Natalie’s parents offered to continue to pay you to act as their daughter’s friend/social caretaker/amateur second therapist after you graduated? Would you be tempted to put your own career on hold in order to continue caring for her? Might you eventually come to resent this situation, regardless of how much money you made? What’s the worst-case scenario if you accept this offer, and are you prepared to accept it? My inclination is to say this: If you can think of any reason to say No, you probably should.

Q. Gender questioning: I’m 21 years old, and for the last few months I’ve been questioning if I might be a transgender man. In a lot of ways it makes sense, but I don’t relate much to the stereotypical trans narrative, and there are some other things I can’t seem to get past. It’s not something I considered before now, and I don’t feel like continuing to present to the world as female would make me so miserable I couldn’t live a reasonably good life.

I’ve asked my girlfriend and a few close friends to try using a different name and pronouns for me, but when they refer to me that way, it mostly makes me feel fake and anxious. I have a referral for a clinic that can provide therapy and/or medical transition, but due to the medical system in my country, that won’t happen for at least a year. If I haven’t decided for sure by then if I want hormones, it will probably be another year after that before I can access them.

Do you have any ideas for trying to work through what I’m feeling? I feel like I’m not making progress with this at all.

A: One thing that may prove a relief to you is this: There are a lot of trans narratives. “Being so miserable I couldn’t live a reasonably good life [without transitioning]” is not a necessary precondition for transitioning. What you’re doing right now—asking yourself questions, exploring different names and pronouns with a few close friends, and contemplating accessing services from a gender clinic in the future—is all exploratory, open, and completely alterable. You’re not committing yourself to anything right now, and you don’t have to do anything that doesn’t feel right or like something you’re ready for. I don’t know if test-driving a different name or pronouns with some of your friends makes you feel “fake and anxious” because you believe you don’t have a “legitimate” basis on which to do it or because the name and pronouns don’t suit. That’s a question only you can answer. I will say that it’s not at all uncommon for people in early transition to repeatedly ask themselves, “Wait, but am I trans? This may make sense for other people, but does it make sense for me? I haven’t always felt this way—why do I suddenly care about something that used to feel neutral, commonplace, or even fine?”

My best advice in trying to “work through” this is to continue to give yourself a lot of time, pay close attention to how you feel when you try new things, and remember that any outcome from this process is a good one. If you spend the better part of a year exploring your options and talking through your feelings with the people you love, then that is a good thing, regardless of whether you transition.

Q. Friend hacked into my Facebook: My ex-friend is an alcoholic, and I believe she has borderline personality disorder. She went to jail a year ago for arson and resisting arrest and has since had police at her house twice. After her time in jail, I picked her up and let her stay with me. I tried to be a supportive friend for 11 months, and she just continued to be a manipulative bully. I stopped speaking to her, so she hacked into my Facebook and read all my personal messages. I will never speak to her again, but I am so angry I am having trouble getting over it. Any suggestions?

A: Therapy! It is often helpful to spend some concentrated time with yourself and a nonjudgmental, supportive professional as you work through questions like, “Where is this anger coming from? What am I angry at in myself, and what am I angry at in my former friend? What can I do with my anger, besides stewing in it or trying to force it away?” Anger seems like a perfectly sensible response to what you’ve experienced in the last year, so don’t feel like your job is to get rid of it as quickly as possible. That doesn’t mean you want to feel this stuck and resentful for the rest of your life—merely that it’s an emotional response worth cataloging, investigating, and spending some time with.

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Q. Re: No strings: This is so easy to swing into a win-win-win situation! Natalie’s parents are grateful to you for all you’ve already done for her, which you did without any expectation of payment. They have tons of money—easily enough to pay for your tuition. Natalie clearly cares about you and values your friendship. Why not tell her parents that you cannot accept money for being Natalie’s friend but that you appreciate their offer to help you stay in school? Maybe they would give you a no-interest loan for tuition. Maybe they would tell Natalie, “We have seen how much [the letter writer] means to you and want to help [him/her] stay in school. We’re going to pay [his/her] tuition so [he/she] doesn’t have to drop out.”

Make it an unexpected gift of gratitude for what you’ve already done rather than a quid pro quo. If you would stay friends with her without the money, then I don’t think you have to feel bad about her parents helping you stay in school. Figure out what you’d be comfortable with, and tell them they must find a way to make it something Natalie supports and knows about.

A: This is the second live response that recommends just such a canny, diplomatic strategy! If it works, I’ll profess myself amazed and impressed. The only thing to bear in mind before making such a counter-request, I think, would be what the letter writer would and wouldn’t be willing to do if their response was, “No, it’s this or nothing. You either take the money on the condition of your employment as a secret paid companion, or it’s all off.” I don’t think that’s the likeliest outcome, but it should be prepared for, in any case.

Q. Chronic interruptions: Whenever anyone talks to my dad, he has a bad habit of interrupting. I find it incredibly frustrating. Whenever he and I speak, I feel like I’m never able to express my point before he interrupts.

I have told him before that this bothers me. I’ve tried many times to get him to stop, both politely (“Can you please let me finish?”) and not so politely (“Stop interrupting me!”). Any way I go about it, he always ends up yelling, blaming others, and being in a sour mood for the next few days. It has gotten so bad that I now often avoid unnecessary conversations, which also angers him because I talk about things with my mom instead of him. I don’t want to make him feel ignored, but more often than not a simple conversation leaves me feeling unimportant and disrespected. I suffer from depression, and the stress of talking to him can leave me down for days at a time. How can I get my dad to stop interrupting and be more respectful of the people around him?

A: I don’t think you can get your dad to stop interrupting you, but you can decide to cut your conversations short if he’s not able—or even trying!—to self-correct, and decline to take responsibility for the subsequent temper tantrums he throws. “Dad, I love you, and I want to be able to talk to you, but when you don’t let me finish a sentence, we can’t have a real conversation. I’m sorry this upsets you. I know you’re capable of doing this. Let me know when you feel calm enough to talk again.”

Q. Re: Gender questioning: I am not trans, but I did change my first name when I was 19. At first, I was excited, but after a short while, I too felt like I was doing something sort of fake. Then I went through a phase of being just tired of the whole hassle and wishing it was over. And then I settled into my new name, and 30-some years later, I’m still happy I made the change.

Names are part of our identity. Changing names is a big deal, even without the trans part of it, which is obviously also huge. I’m just saying that feeling odd while making the change does not mean it’s wrong. It’s just part of the process.

A: Thanks for sharing this! That’s not to say that anyone should dismiss feelings of “I’m not sure this is right,” but it is helpful context to know that lots of people who change their names go through a period of feeling self-conscious and arbitrary.

Q. Re: No strings: I think you missed the boat on this one, Prudie. Natalie’s parents aren’t asking for an employment contract. The letter writer and Natalie are already friends, and the letter writer has been involving Natalie in social outings. The letter writer needs to leave school for financial reasons, and the parents don’t want to let that happen. They are offering to help out their daughter’s friend, not buying one for her, and I don’t see anything from the letter writer that indicates he or she has been trying to dump Natalie. I see nothing wrong with the letter writer gratefully accepting financial assistance from Natalie’s uber-rich family and continuing to be a friend to Natalie. Years of college tuition—that’s nothing to throw away because of awkwardness around money and accepting gifts.

A: That’s a generous reading of the situation, although you may very well be right. I’m inclined to think of any gift that comes with preconditions as not especially freely given. If they simply wanted to look out for the letter writer, why wouldn’t they simply offer to pay the tuition? Why are they trying to keep this arrangement a secret?

I don’t think the letter writer is looking to dump Natalie either, but it does seem apparent that she doesn’t want to be Natalie’s only social outlet or companion in the long-term and might want to take a step back from the kind of friendship they’ve had over the last few years. All of which seems perfectly reasonable and doesn’t at all mean that the letter writer doesn’t care very much for Natalie and her continued well-being!

Q. Ghosting: My brother is in his mid-30s. He has dated a couple of women who have “ghosted” him, one after a few dates and one after a few months. This was, understandably, very upsetting to him. However, I’ve just discovered that he did the same thing to a nice woman he recently had a couple of casual dates with because he didn’t see “long-term potential.” I’m of the do unto others school of thought and don’t think this is OK, since he has been hurt by the same action in the past. When I broached the subject with him, he became defensive, and I backed down. What is your opinion of ghosting versus just being honest?

A: I think ghosting after a couple of dates, even fairly casual ones, is generally unnecessary and less than kind. That said, you don’t have to convince your brother that he needs to make changes in his dating life unless he’s doing something really egregious, so I think your best option here is not to ghost people yourself and let your brother make his own mistakes in dating.

Q. Re: Chronic Interruptions: Has your dad had his hearing checked? This can be so, so common when people begin to lose their hearing.

A: That’s certainly possible, but the letter writer doesn’t say that this is a recent or sudden change, and if Dad gets this defensive about being told he’s interrupting, my guess is that he won’t respond much better to, “Have you gotten your hearing checked lately?” But it’s worth bearing in mind.

Q. Possibly depressed friend: My best friend recently started a new, more demanding job with slightly odd hours. She never comes to group plans anymore and is gone in a flash when she does. She hardly replies to texts anymore. She seems sad and withdrawn and is constantly talking about how hard of an adjustment her schedule is. On the one hand, I’m genuinely hurt. It feels like her new job is far more important to her than her old friends. On the other, I’m worried about her. She seems drained, sad, and tired. What’s a good way to tell her that I’m worried about her but that her flaky, withdrawn behavior is unacceptable?

A: I think the “worried” part of the conversation needs to happen before the “unacceptable” part, especially since this is a fairly recent change and the two of you haven’t yet discussed it. I’m not sure yet that her job is more important to her than her friends; I think her new job is exhausting her. Tell her that you’re worried and that you’ve noticed her sudden withdrawal from your social circle, but ask how she’s doing and whether she thinks she’s able to continue with this schedule, rather than heading straight to, “This is unacceptable and you need to straighten up.” It sounds like your friend needs help rather than censure.

Q. Poly supportive: My husband’s younger sister recently told us she’s in a polyamorous relationship with another couple. We are supportive and look forward to meeting and establishing a relationship with the other couple and their children.

My sister-in-law and her three children were planning to visit us next month. Due to distance and finances, we are only able to see them once a year. My sister-in-law would like to bring her partners and their children, but my husband is hesitant. His sister is his only living relative, and he cherishes the few days a year he gets to spend with her. He says he understands he is being selfish, but he really wants one more visit with only his sister and nephews. He wants to meet the rest of her family when we visit them next year. Is this a reasonable request?

A: If she’s already expressed a desire to bring her partners and their children (especially in the wake of having told you for the first time about her relationships), then it might be a bit difficult to ask her to wait another year to introduce you. But your husband should make sure to schedule at least one day where he gets to have some uninterrupted sibling time with just his sister and his nephews, before continuing to get to know the rest of the clan.

Q. Re: Gender questioning: You need to know it is perfectly acceptable to be a “butch” lesbian. Liking “guy” things, short hair, etc. does not mean you are trans. It seems that more people are pressuring both butch lesbians and femme gay men into considering if they “really are” trans. I’ve faced it.

A: I do not believe the letter writer betrayed any sort of belief that it was not acceptable to be a butch lesbian (or even that they have ever identified as such). It is absolutely true that what clothes one likes to wear, or what activities one enjoys, does not make anyone cis or trans. Suggesting, however, that there is some sort of implicit, sinister trans agenda attempting to pressure gender-nonconforming gays and lesbians into transitioning against their own desires unnecessarily pits queer identities against one another, and ignores the existence of trans lesbians and gay trans men (and all manner of trans people who remain gender-nonconforming!).

Mallory Ortberg: Thanks for a lively chat, everyone! See you next week.

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Mallory Ortberg, Slate’s Dear Prudence, is co-founder of the Toast and the author of Texts From Jane Eyre and The Merry Spinster.