Dear Prudence

Dying to Catch Up

I’m worried about a long-lost friend. How can I reach out?

Reading a shocking story in a magazine.
Photo illustration by Slate. Photos by Thinkstock.

Dear Prudence,
Twenty years ago, I worked at a university admissions office. My co-worker “Betty” and I spent a lot of time together—we ate meals together, went shopping together, visited each other’s homes, and shared confidences. After I left that job and moved away, our contact gradually tapered off; we last spoke about five years ago. Last week I received an alumni publication and noticed that Betty was receiving an award. The accompanying photos gave me a shock. She was shockingly thin, wore a hat or a scarf on her head in every photo, and generally looked as if she was suffering from a serious condition, although her health was not mentioned in the article. I want to call her to express my concern and have what might be a final conversation. I don’t know how to begin. I’m pretty sure I shouldn’t start with, “Gee, Betty, you look awful. What’s up?”

Ten years ago a childhood friend died of a brain tumor while I lived across the country and I didn’t find out until she was in hospice and unable to speak. She died a few days later and I still regret that I never could tell her what she meant to me. How do I approach this conversation with Betty? I should add that I only have her work number and usually get her voicemail.
—What to Say

That instinct not to open with “You look terrible, what’s wrong?” is a good one, and I suggest you follow it. Luckily, the recent award gives you a perfectly plausible reason for re-establishing contact. If you keep getting her voicemail, try calling the main line at her office and asking if there’s an email address she checks more frequently or a better way of getting in touch. Tell her you saw the notice of her award and wanted to congratulate her and say hello, because you remember those years you two worked together so fondly. If Betty has a fatal disease, it will almost certainly come up naturally while you catch up. If she doesn’t—or if she declines to mention it—you can still have a pleasant conversation with an old friend. You won’t regret calling, but you might regret fishing for information if it turns out Betty isn’t sick at all. Even if she is, she might not have the energy to go into details with an old work friend, regardless of how much you two enjoyed one another’s company 20 years ago. Whether or not Betty is dying, it’s always nice to speak with someone you care for but haven’t seen in years.

Dear Prudence,
My partner of almost five years has recently been experiencing some strong feelings of gender dysphoria and changing their gender presentation. I think it’s great they’re talking about it and trying new things, and I’m totally on board. But I was wondering if you could offer any advice about specific things I can do to support them. I’ve given them a binder and some clothes they’ve asked for as gifts and tried to be available as a listener. But not having gone through any sort of similar experience myself I don’t know if there are common pitfalls to look out for or if there are other things I can be doing to help!
—Hopefully Helpful

A supportive attitude and a desire to be useful puts you at least 90 percent of the way there! I think the most common pitfall you’re likely to experience is an excess of that desire, of wanting to be so useful that you begin to think of your partner’s dysphoria as a problem you can solve with sufficiently high levels of empathy and support. That’s a recipe for failure and frustration. You can listen and offer reassurance to your partner, but they may continue to experience dysphoria in one form or another for a very long time, even for the rest of their life, so don’t think it’s a reflection on you (or how supportive you are) if your partner’s struggles with dysphoria don’t immediately improve. It may help you to find a community (either online or IRL) for other partners of trans/genderqueer folk, to talk through your own goals and concerns; you might also ask to hear from other people who have been in similar situations about what’s worked for them.

And go easy on yourself when it comes to saying things like “I haven’t gone through any similar experience myself”—you don’t have to have experienced dysphoria firsthand in order to be helpful and loving towards your partner. You don’t, in fact, have to perfectly understand anyone else’s experience in order to help. Listening, asking specific questions, being open-minded and supportive—you’re already doing everything a good partner does.

How to get advice from Prudie: 
• Send questions for publication to prudence@slate.com.
(Questions may be edited.)
• Join the live chat every Monday at noon. 
Submit your questions and comments here before or during the live discussion.
• Call the voicemail of the Dear Prudence podcast at 401-371-DEAR (3327) to hear your question answered on a future episode of the show.

Dear Prudence,
I go to a small university in a small city and live together with five friends in a house we rent out. This situation is wonderful—apart from one friend, “Ellie.” Ellie has severe mental health issues, as do many of us in the house. (I myself am in the middle of a major depressive period, which I am in treatment for.) Ellie spends most of the day in her room, posting on her Twitter account (we all follow each other) about how depressed she is, about acts of self-harm she wants to commit, about how much she wishes she could be with her friends (we are her only friends), and about how suicidal she often is.

I understand she needs to vent, but this is difficult to deal with when we are constantly reaching out to her, trying to help her get help, saying that we are here if she wants to talk, and generally trying to help the best we can. Her tweets are hard to read and often seem intended to make us feel bad about hanging out without her, when we invite her constantly and she ignores our invites! We have suggested therapy, and one of our friends has physically gone with her to student support services. These constant posts about how miserable she is when she will not accept any help make us feel awful, and we’re becoming less and less sympathetic. This has been going on for months. How do we deal with this?
—Home Stuck in Hell

Unfollow your housemate on Twitter. If you absolutely can’t bring yourself to that level of low-level conflict, then mute her. You do not need to read minute-by -minute updates on how she is experiencing her depression. Continue to be kind and supportive, attend your own therapy sessions, and stop reading her Twitter feed. It’s a place for her to vent, and there’s no reason for you to watch that venting take place if you’re already offering her support in real time and it’s affecting your own mood.

Dear Prudence,
I’m in a supervisory position in a field in which hierarchy is taken pretty seriously—in other words, it would be considered inappropriate for someone I directly supervise to approach my supervisor about an issue without coming to me first. I have a new employee who is fresh out of college and eager, if insecure. I’m not much older than her, but I have much more experience. She often comes to me with questions that I think she’s capable of researching herself, but I try to help her the best I can, remembering that she’s new and probably overly cautious.

The thing that really annoys me is when asks me a question, I give her an answer, and then she poses the same question to my supervisor in a later meeting with both of us present. To me, this makes it look like she didn’t trust the answer I gave her. To my supervisor, it looks like I didn’t know the answer in the first place or like I’m not communicating clearly with my team.

For the record, each time this has happened, my supervisor has given her the exact same answer I did. I don’t want to embarrass her in front of my boss or seem like I’m being defensive, but I also don’t want my boss to think I’m not doing my job—and honestly, I’m offended that she doesn’t trust my expertise. I can’t tell if she’s doing this just to appear thorough in front of my boss or what. How do I handle this without seeming like I’m too consumed by my image? I’m really worried about appearing incompetent.
—Can I Tell My Subordinates to Quit Making Me Look Bad?

The best way to approach this with her is to assume that this is simply one of the nuances of your field that she hasn’t yet grasped. It’s likely that she’s not aware how these duplicated questions reflect on you and is trying to come across like she’s paying attention in front of your supervisor. It’s totally appropriate for you to outline as clearly as necessary what’s considered company-appropriate behavior. “I’ve noticed you often ask my supervisor the same question you’ve recently asked me. If I ever give you an answer that’s unclear or that you have follow-up questions on, please let me know so that I can clarify things for you. Since supervisory roles are so clearly defined here, it’s unusual to ask questions of your boss’s boss, and it makes it seem like I’m not giving you the information you need to do your job. If there’s something you need from me that you’re not getting please let me know, but otherwise I want you to come to me with your questions, and if I’m able to answer them, to not trouble Croesus with them.”

More Dear Prudence

Help Not Wanted: Prudie counsels a letter writer who’s embarrassed to use government-sponsored insurance.

Up in Smoke: Should I let my pothead son burn through his college fund?

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

Dear Prudence,
I am a twentysomething woman who is interested in women but hasn’t yet dated one. At the moment, I have a mild crush on one of the baristas at the coffee shop that I go to nearly every day during work. I see her several times a week and we have a fairly friendly customer-barista rapport. I’m not painfully pining away—I just enjoy talking to her and it brightens my day when I see her.

I’m about to leave my job in a few weeks, after which I will no longer be a regular customer at that coffee shop. Part of me wants to ask this girl out or give her my number before I leave, but I am also firmly of the opinion that you should never hit on people at their place of work, especially when that work involves customer service. (I also have no idea if this girl is also into girls.) Should I just let this gentle crush go, as it will almost definitely fade once I no longer see her almost every day?
—Coffee Shop Meet-Cute

You have done such a thorough and effective job of talking yourself out of giving this girl your number that I feel morally obligated to argue the other side. You’re perfectly aware that she may not return your mild crush. You’re also aware of the ways in which she might find it difficult or distracting to have to turn down a customer’s advances at work. Soon you’re not even going to be a customer of hers, which means if the worst comes to pass and she doesn’t give you a call, you’re not putting her in an awkward position. The next time you two are experiencing your “fairly friendly customer-barista rapport” (and there’s not a line behind you), give her your number, and tell her to give you a call if she ever wants to go out after work. Write it down beforehand, tell her you understand if she’s not interested, and leave it there. That’s neither rude nor intrusive and, if nothing else, will help get you used to the prospect of asking other women out. Good luck!

Dear Prudence,
I’ve lived in a lovely two-story apartment with three roommates for six years. We split the utilities evenly. This past month, we received a significant price hike due to the cold snap. I expected the gas bill to be high, which it was, but I was shocked to see that the electric bill was twice as much as last January. One of my roommates suggested the cause was his girlfriend. When she comes over, it’s often for a few days at a time, and she often leaves the space heater running. I don’t blame her, of course, but she doesn’t pay rent or offer to help with the utilities. I asked him if I could talk to her about the bill, and he agreed. My savings have been depleted this year due to medical issues, and it was a real strain to pay the outsize bill.

So I sent a message to her on Facebook: “I know the higher electric bill is partially due to the cold, but as you use space heaters when you’re in the house, and most of us don’t, I wanted to see if you would be willing to chip in on our electric bill this month!” She didn’t respond. My roommate told me that he thought I was going to ask her to use the space heaters less, not contribute to the bill, and that my message “crossed a line.” I apologized to him for the misunderstanding and then sent a separate message apologizing to her. She still has not responded. So, just how badly did I screw up? Should I have waited to talk about the problem when we were in person? Was it rude or reasonable to ask for money point-blank? And if a similar problem comes up in the future, which it might, should I go back to asking my roommate to deal with his girlfriend directly?
—I Crossed a Line (and the Line Won)

In no rational version of events is it “crossing a line” to ask a person who contributes significantly to the cost of the electric bill to chip in for it! Just as it is not unreasonable for my energy company to send me a bill every month, it is not unreasonable for you to ask your roommate’s girlfriend to chip in when your monthly bill is suddenly doubled. It’s almost always better to have this kind of conversation in person, if only to prevent the nonresponse you received. But if your roommate heard you say, “Our bill was unusually high this month,” suggested that his girlfriend was the cause, encouraged you to speak to her about it, and somehow failed to piece together the possibility that you would ask her to contribute—well, the screwup was on his end, not yours. You did not need to apologize to either of them, and I think the next conversation you need to have is with your roommate himself. Since all of you agree the increase in expenses was caused by his girlfriend, in addition to asking her to use the space heater less when she visits, the two of them should make up the difference. If he thinks it’s “over the line” to ask her to chip in, then he is free to spend his own money.

One more thing

You depend on Slate for sharp, distinctive coverage of the latest developments in politics and culture. Now we need to ask for your support.

Our work is more urgent than ever and is reaching more readers—but online advertising revenues don’t fully cover our costs, and we don’t have print subscribers to help keep us afloat. So we need your help. If you think Slate’s work matters, become a Slate Plus member. You’ll get exclusive members-only content and a suite of great benefits—and you’ll help secure Slate’s future.

Join Slate Plus
Mallory Ortberg

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