Dear Prudence

Help! I Resent My Friend’s Over-the-Top Kindness.

Read what Prudie had to say in Part 1 of this week’s live chat.

A smiling woman with a halo above her head.
Photo illustration by Slate. Photo by SanneBerg/iStock/Getty Images Plus.

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

Daniel Mallory Ortberg: Good morning, everybody! It’s too hot out to have problems; let’s just stand under the nearest fan or body of water and try to have problems tomorrow instead.

Q. My co-worker’s niceness is too much of a good thing: My longtime friend and co-worker “Sarah” is bright, caring, and fun. I usually love spending time with her. She is a good person. Too good! I know that sounds like a weird “problem” to have. But in the past couple of years, Sarah has become increasingly focused on being, well … a saint.

We work together in an office of over 30 people. At least once a week, she gives each of us a hand-drawn card, a little gift, flowers from her garden, or a homemade cookie, along with a note about how much she appreciates us and values our friendship. She constantly asks us to bring in potluck food for office lunches or to deliver a meal to any employee who is out sick. She regularly throws themed parties for us in the break room but always needs help to set up and clean up. She asks us to participate in “encouragement” activities—such as passing around a piece of paper with each person’s name at the top and asking us to write on it something we love and admire about that person. For everyone’s birthday, she “celebrates” for the entire week before by giving them daily gifts and surprises, culminating in her asking us to come in an hour early to decorate the person’s office, as well as attend a party for them during our lunch break. Almost every weekend, she participates in some sort of walkathon or other event to raise money for charity and wants us to join her or donate. She keeps a box in her office and constantly asks us to bring in food, clothes, toys, dog food, etc., for charities.

Every week, she sends money to one of us at home, instructing us to use it to do a random act of kindness for a stranger. We are then supposed to post on her social media account an inspiring story of how we spent her money. She also sends inspirational videos, and passes around self-help books, and becomes annoyed at anyone who declines to watch or read what she sent. A group of co-workers went to the owner of the company (there is no HR), saying it was affecting work productivity and morale. He strongly disagreed and now praises her at almost every staff meeting for being such a “fine Christian woman,” urging us to follow her example.

I think it’s wonderful that she wants to help others. And it’s easy enough for me to set boundaries with her on how much I’m willing to help. But it’s much harder to deal with the emotional fallout if I don’t. She constantly expresses disappointment that she failed to get enough participation or didn’t get as much praise, thanks, or positive feedback as she was expecting. More painfully, she often expresses how hurt she is that we apparently aren’t willing to do as much for her as she does for us, which she takes as personal rejection. Recently, she was bemoaning the fact that no one had left any “surprises” on her desk for the past three weeks. I gently tried to explain that while we all appreciate her thoughtfulness, it’s just too much. We can’t keep up! She became very upset and said that she isn’t going to stop being a good person just because the rest of us “don’t care enough” to step up our game. She didn’t speak to me for two weeks.

Today, I got a long letter from her telling me she forgives me for trying to dampen her joy. She explained that she’s just trying to be a good person, to make the world a better place, and to help us all become better people. She says she isn’t going to let my negative attitude change that. She expressed her belief that I probably don’t care about her as much as she cares about me, but that’s she is willing to accept me without trying to change me and hopes I will do the same for her. I feel horrible! I do care about her. It’s not personal. Most of us quietly do our own volunteer work or donate to our favorite charities outside the workplace, and in my opinion, it’s not realistic to expect all of us to devote as much time and energy to this as she chooses to, especially in the workplace. I have no clue how to respond to her letter. I thought about talking to her about the different “languages” people use to express their love, but this seems like a deeper pathology than that. What do I say now?

A: I don’t think you have much of a friendship to lose here. This seems like a wonderful opportunity to accept her offer of condescending forgiveness and say, “Thanks for understanding!” Then continue to focus on your own work, decline to help her organize the next 50 fundraisers she’s got planned for the summer, accept that you are never going to be able to convince her that her anxiety-driven and compulsive need to manufacture acts of ostentatious niceness are maybe—just maybe—sometimes a little exhausting, and treat her like a slightly difficult co-worker rather than a friend you can win back to your side.

Q. I’m the trashy housemate: I grew up poor and have dumpster-dived at various points in my life. Recently, with increased bills and a lack of job prospects, I have been going through the house trash. I live with a few other people. I tried to be discreet but got caught. The woman who caught me has graciously not said anything, but I know she saw me washing some nearly new monogrammed towels she threw out. (I had planned on using them after removing the embroidery.) I am worried about broaching the subject. She is too kind to bring it up, but should I say something? I feel like she might just chuckle and tell her friends in passing, which I don’t really mind. I don’t know them, and they don’t know me. Should I just quietly apologize to her?

A: I’m so glad your housemate has been kind and laid-back about the whole thing. You can, if you’d like, acknowledge the awkwardness of the situation and say, “I’m sorry I didn’t think to double-check with you, but I was planning to remove the embroidery and then use them myself. I hope that’s all right with you.” You can add something about being a keen up-cycler or craft enthusiast, or even let her know that if she’s ever thinking of getting rid of something that’s still useful, you’d be happy to take a look at it first. But if you don’t want to get into the details of how you’re making ends meet right now, I don’t think you have to. She’s made it clear that she’s comfortable with the situation and doesn’t seem likely to ask any leading questions. I hope things turn around soon and that in the meantime you get a lot of use out of those towels.

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Q. Cis people and gender-segregated spaces: I was recently trying on clothes and there was a long line for the women’s changing rooms (fully private stalls) but not for the men’s. I started to head toward the men’s rooms and the attendant stopped me and told me I couldn’t go there. I said, “You don’t know my gender!” and brushed past her. I’m not trans, but in the moment, I felt like whatever my gender identity is, it’s not consistent with waiting in line for one set of changing rooms when there are empty rooms right there because of someone’s ideas about gender. But now I’m wondering if that reinforces the harmful fiction that trans folks are just using gender identity to access the “wrong” gendered spaces?

A: The good news is that the moment’s now past, it was a relatively low-stakes issue, and there’s a rich non-trans-related history of people eventually giving up in frustration after waiting in a wildly long line and just going for whatever bathroom or changing room is closest, private, and available (and of course, no one was actually harmed by you trying on a few culottes or whatever behind a closed door). But I think you know “My gender identity isn’t consistent with waiting in line for a set of changing rooms when there are empty rooms right there” isn’t really why you decided to make a run for it. Which is fine! It was an arbitrary division that, at the time, wasn’t serving anyone well, and I certainly understand why you made a common-sense, in-the-moment decision—you just don’t need to try to ground it in some sort of claim about your gender in order to defend it. I do think it’s interesting that the first line you went for is a soft anti-trans cliché (trans people usually don’t say, “Don’t assume my gender identity”; non-trans people looking to emphasize how unreasonable, hypersensitive, and demanding they think trans people are often do)—there’s at least some unconscious association, on your part, that calling yourself trans means you get to flout public line-standing convention and no one gets to question you. So in that sense I wouldn’t advise you to say something like that again! But you can certainly say, “Look, this line is incredibly long, no one’s using these, and they’re all single-stall. I’d like to use what’s available.”

Q. Quilt: My mother saved her own wedding dress as well as those of our grandmother and great-grandmother. My sister stored them, but all three got damaged when her roof got hit by a storm. She gave them to me. I did look into restoring them, but that would cost hundreds of dollars with no guarantee of a full restoration. None of my nieces would ever fit in the dresses, and I doubt they would want to wear old dresses. So I saved the lace and all the trimmings and then turned the wedding dresses into quilting squares. I finished the first one and gave it to my oldest niece as a birthday gift. She was extremely touched and cried when she saw it. Her mother was enraged. She accused me of “desecrating” the dresses and destroying our family history. I was shocked because she never had any stipulations when she gave me the dresses. I argued she could have gotten them restored herself if they were that important to her. I am an avid quilter. Giving me old clothes is basically asking me to make you a quilt. I told her she was out of line, but I offered her the lace and trimmings so the girls could have something old for their weddings. She called me a bitch. We are not talking now, but the rest of the family is oblivious. My other nieces are asking when they can get their quilts, and they even thanked me for giving them an heirloom they can “actually use.” I don’t know how to heal this breach with my sister. I don’t know what I did wrong, honestly—the dresses have been sitting in a dusty attic for six years since our mother died. Neither my sister nor me was married in them.

A: I mean this totally sincerely: Congratulations on not responding in kind when your sister called you a bitch for rehabilitating some nearly ruined antique dresses. It can be really difficult not to lose your composure when a sibling goes from zero to 60 over a perceived slight, and I’m so glad you remained calm, offered her a compromise, and then stepped away when it became clear she didn’t want to meet you in the middle but hang on to her anger for dear life. I understand that family heirlooms can bring up a lot of deep feelings, but I don’t think you did anything to merit your sister’s response—mostly, I think, it’s not going to be productive to try to establish whether you broke an unspoken rule. The best possible way out of this fight will come from talking honestly and lovingly about your expectations and your feelings, not from proving you should have or should not have asked her for permission before restoring or altering the dresses. (And if she decides that nothing will ever heal her distress over these dresses, that would be a shame. I hope she eventually decides to lay down her grief.)

Q. Baby boredom: Me and my best friend from university are almost in our 30s. She has two kids, while I have no interest in having them. We live across the country from each other, and I try to fly down every year to visit since I understand that’s a lot more difficult for her. We keep in contact through texts when we can. However, 99 percent of our conversations just end up being about the kids. She doesn’t ask about my life and acts very shocked when she doesn’t realize something important has happened to me. I love her and I love her kids, but it often feels like I’m just a sounding board to talk about what kind of birthday her 2-year-old should have. Is there a way I can kindly tell her that I would like her to take some interest in staying involved in my life as well?

A: Yes, of course! You said it pretty well here, and you can definitely say it to her: “I’ve realized lately that there have been some pretty significant life events I haven’t been able to keep you updated on, and I miss feeling like you know what’s going on with me. I love hearing about how the kids are doing, but sometimes I want to set aside a little time to talk about something else. Can we do that?” My guess is that your friend isn’t doing this on purpose and doesn’t always realize when she has her Kid Goggles on. Once you’ve established that it’s a pattern you want to change, I think it’ll feel much less uncomfortable to make an in-the-moment intervention: “OK, I want to tell you about _____ now. Mind if we take a break from kid talk?” (My guess is, as much as she loves her kids, she will enjoy every once in a while being reminded that she’s allowed to talk about other things. This will probably feel like a relief to her too!)

Q. Patron of the arts: I met “Henry” while were both attending college. At the time, he was still in an emotionally, mentally, and financially abusive relationship that had consumed most of his adult life (he was in his early 30s when we met) and left him isolated. A friendship immediately blossomed, I helped him escape that abusive relationship, and we became best friends. He is by far my dearest friend and he has literally saved my life. This friendship means everything to me.

After leaving his ex, he moved in with a friend, where he lived for a year rent-free. During this time he swore to himself and everyone else that he would put himself back together again and fix his financial situation. He didn’t, in part due to his extreme depression, and when he moved out to an apartment with two mutual friends of mine, he struggled to make rent. Before getting in that abusive relationship, he worked retail and despised it so much he vowed to avoid doing that line of work at all costs. He’s attempted to make all of his money through freelance art, but with a few exceptions, he has failed to make rent and has relied on either me or his ex to foot the bill. By the halfway point in his lease, I was paying his rent every month, not to mention almost all of his bills and food costs. He also dropped out of college. I have asked him to get a job multiple times, but each time he gets extremely defensive and promises to work harder on getting commissions or to donate plasma—anything to avoid getting a job. It never works, and I end up paying for everything.

He’s now moved to a new apartment, a beautiful place with very low rent, and he shares the place with two of our closet friends. He could work part time and easily cover his expenses. Despite promises to do better, I’ve ended up paying his rent for these first few months. He’ll call me about his plan to write a novel, start a comic strip, a Youtube channel to make money—all long-term goals with no promise of payoff, but he never gets a job.

Before, I was able to easily afford all of this, but recently my financial shape has changed for the worse, and continuing to pay his rent will severely hurt my wallet. I also don’t want to place the financial burden of covering his share of the rent on his roommates, who wouldn’t be able to afford it. But it’s now the middle of the month, and instead of following through on his latest promise to get a job, he told me he’s going to try to use a new freelancing website to make ends meet. I’ve begrudgingly started to put money away for next month.

What can I do? I feel like I am trapped in a cycle. He gets so depressed and stubborn that it’s clear that if I stop paying for him, he’ll willingly let himself, his pet, and his roommates go homeless just to avoid getting a job. He’s a talented artist, but it isn’t paying the bills. I am paying for everything. I can’t even enjoy life anymore because I have to think about the money I’m going to use to pay for him. Financial help from his family or other mutual friends isn’t an option. Please help me.

A: “I can’t afford to continue covering your rent, so you’ll need to find another arrangement starting next month.”

Q. How do I get my mom into therapy? My mother has been an anxious and depressed person my entire life. She was adopted into a verbally abusive and neglectful household as a toddler. She has always felt a sense of loss for not knowing her biological parents and for being told by her adoptive mother that she was not wanted. To this day, my mother has a fear of her loved ones leaving her. This can make her overbearing and depressed around her children. This has come up recently because my sister is getting married. My mother gets extremely distressed when she feels excluded from the wedding planning. She also views my sister’s fiancé as an outsider and has a hard time feeling comfortable around him. She acknowledges that she is sad but refuses to seek therapy because “talking about sad things will not make them less sad.” My family has tried multiple times to suggest therapy, but it always ends with her getting offended, crying, and denying that her depression is affecting her life. My siblings and I have all sought therapy of our own at her suggestion, which makes the situation more confusing. What specific language or techniques can I use to get her to consider getting help?

A: At the risk of sounding super Al-Anon-y, I do think the most important question for you is not “How can I convince my mom of the merits of therapy?” but “What do I need in order to have a meaningful relationship with my mother, even if she never gets therapy or gets any better at dealing with her anxieties, fears, and traumas than she is right now?” That might mean ending some conversations early, even conversations where your mother is visibly upset, because you know that there’s no level of involvement in her daughter’s wedding that would make her feel safe from abandonment.

You can, of course, lovingly challenge some of her assumptions about therapy, especially if you want to talk about your own experience: “I didn’t find that therapy was about making sad things ‘less sad’ so much as identifying patterns of behavior that I might want to change, figuring out what strategies I’ve used to cope that have helped keep me safe and peaceful, talking through my goals for the future—it was mostly just about having a dedicated time every week to talk about my feelings with someone who thinks about feelings professionally. I didn’t always have a breakthrough, but I got a lot out of it, and it sometimes made my fears and anxieties feel a little less huge or all-encompassing.” But beyond that, I think all you can do is offer the occasional encouragement, let make her own decisions about therapy, and cut conversations short if it seems like she’s using you to spin out anxious fantasies about being cut out of the wedding.

Q. Bickering in public: One of my close friends and her husband have an uncomfortable habit. They both like to make rude or snide comments to each other in front of people. When this first happened, I thought they were just having a rough day and couldn’t help but make passive-aggressive comments in front of me. It happens.

But as I have been around them together more and more, this happens every single time. Although they both do it, her husband tends to do it far more. In speaking with my friend one on one, I know she has issues with her husband. I talk through it with her. Listen. Regularly suggest therapy. I’ve sort of just resigned myself to sitting through the uncomfortable moments when they decide to be rude to each other. But I’m wondering, should I say something to my friend, should I just get over my discomfort and bite my tongue, or should I call out their rudeness in the moment?

A: I think it’s important to think of it not in terms of “calling out their rudeness,” which can easily lead to defensiveness and the two of them turning their snappishness on you. But yes, you can and should say something: “I’m sorry you two are having a difficult time right now, but I’m not comfortable listening to you talk to one another and listening to you speak to them like this. I’m going to leave so you can have some time to address this together.” It’s also important, I think, not to treat this like “You’re being rude so I’m taking my ball and going home!”—you’re not punishing them by withholding your presence from them until they can behave. You’re letting them know that they’re trying to rope you into an unkind, unhealthy private dynamic and that you aren’t interested in participating.

Q. Re: Cis people and gender-segregated spaces: Stop-loss monitoring in clothing stores is often monitored by same-gender personnel. You created a situation where the man in charge of monitoring that space was made to monitor you without having consented to that.

A: You will have, I think, a difficult time convincing me that a shoplifting monitor was significantly harmed or that his consent was meaningfully violated by watching a woman go behind a closed door with the words men’s fitting room over it.

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Classic Prudie

Q. My secret crush says he loved me too—but now we’re married to other people: I was secretly in love with a close guy friend of mine for many years. We’re now in our 30s and both married (to other people) with children. I haven’t heard from him in a while, despite reaching out to him about once a year. I just received a response to my latest attempt to reconnect, in which he admitted to pushing me away because he had been in love with me and it took him a long time to accept that things were not meant to be! I no longer have feelings for him and am happily married. I’m just angry with him for only saying it now. I’m having trouble shaking the feelings of anger and resentment. I haven’t responded yet, and I’m wondering—should I respond and say, surprise, I felt that way too, or just let it go? Even though I’m angry, I don’t know if it is a good idea to basically do the same thing to him at this point in our lives and make him reconsider past actions. But I wonder if being honest will give us both some closure. Or maybe it would just make me feel better to tell him the truth, finally. What do you think?