Dear Prudence

Analyze This

Prudie advises a letter writer who wants to break up with her fiancé via his therapist.

Mallory Ortberg
Mallory Ortberg.

Photo by Sam Breach

Mallory Ortberg, aka Dear Prudence, is online weekly to chat live with readers. An edited transcript of the chat is below. (Sign up below to get Dear Prudence delivered to your inbox each week. Read Prudie’s Slate columns here. Send questions to Prudence at

Readers! Ask me your questions on the voice mail of the upcoming Dear Prudence podcast. Just leave a message at 401-371-DEAR (3327), and you may hear your question answered on a future episode of the show. 

Mallory Ortberg: Hi, everyone! Hope you’re all ready to strive onward and upward toward greatness. Let’s chat!

Q. Engaged but not happy: Over the holidays I got engaged. My boyfriend has clinical depression, and the holidays are rough on him. I was going to break up with him, but I held off, thinking it would be easier after the holidays. Then he surprised me—at his parents’ house in front of his whole family—with a ring. I didn’t see how to say no without humiliating him in front of his family, so I accepted. I’ve been trying to break it off ever since, but something always stops me. He had problems at work, and then it was Valentine’s Day, and then he had a medical scare. I keep picturing myself marrying him because I don’t have the nerve to break up with him. He has a therapist he trusts implicitly. Would it be wrong to ask her to tell him?

A: Oh my God, yes, it would be wrong. It would be a violation of roughly every standard of behavior in her profession, and it would be deeply cowardly on your part. You cannot marry someone you do not want to be with just because he has depression and you’re afraid of hurting him, but you also can’t fob off break-up responsibilities onto someone else just because you don’t want to see his reaction. I have sympathy for your original plight, I truly do (public engagements carry a lot of implicit pressure), but you absolutely have to break up with your fiancé in person, by yourself. Go see a therapist of your own if you need help mustering up the strength, but there is no other way out of this relationship. You have to break up with him on your own behalf.

Q. Husband telling people I have borderline personality disorder: I recently found out from a friend that my husband has been telling our friends that I have borderline personality disorder. I was completely flabbergasted and shocked, because I have never been diagnosed with this in my life. I confronted my husband, and he refused to talk to me about it, saying he didn’t feel “safe” talking to me. I immediately made an appointment with my therapist and explained the situation to her. She reassured me that I do not, in fact, have BPD. I again talked to my husband, told him to stop lying, and that I wouldn’t stand for it. He agreed but did not apologize.

A few weeks later, I checked his texts (I know—cardinal sin of marriage), and saw that he had drunk-texted his colleague at 11:30 at night that I had BPD. (He was so drunk that night that he threw up after he DROVE himself home.) I’m at a loss. We’ve been having marriage problems due to lack of trust. He lies to my face frequently, e.g. will tell me he was at work all day, and later I will find out that he had spent the whole day at the shopping mall. Or he will come home late reeking of alcohol but insist he never had a drop to drink and was at the office the whole time, and later I find the receipts showing he had gone out drinking before coming home. I think this is the last straw, but I don’t know what to do. He has been trying to be a better husband in a lot of ways (has stepped up his contribution to housework, is learning to cook, makes lots of thoughtful gestures, etc.), but he continues to lie and refuses to apologize. He just says I’m in denial about BPD and asks why it bothers me so much that he tells other people. He says he’s just worried about me and “looking for advice from friends.”

A: I think this is the last straw too, and I think I know what you should do: I think you should leave him. This is abusive gaslighting of the highest order (“a form of mental abuse which a victim is manipulated into doubting their own memory, perception and sanity”). You have plenty of reasons to end your marriage already, between his chronic lying and drinking, but when you add to that list the fact that he has repeatedly lied about your mental health to your friends and refused to apologize (!!!) when confronted with this fact, what you have is less of a marriage and more of a hostage situation.

I don’t believe your husband is worried about you in the least. I think he’s interested in making you doubt yourself, in feeling isolated, in keeping you in the dark, and in controlling you. I don’t care how many dishes he washes. This is a person who will ruin your life, and I hope you can find somewhere else to sleep tonight. Don’t let his half-hearted attempts to pick up more dirty socks convince you that you’re suffering from a mental disorder you don’t have, then doubling down by suggesting you’re “in denial” when you call him out on his vicious lies. Put as much time and distance between the two of you as possible. While you’re at it, I think you should look for a different therapist. Any therapist whose patient says, “My husband is telling people I have BPD when I don’t, then refuses to acknowledge or apologize for his lie when I call him on it,” and doesn’t suggest that you consider leaving is ineffective and lazy at best. Find a therapist who can accurately reflect reality back to you and who understands what a fundamental and horrific betrayal this is.

Q. Mother’s Day: My mother does not like me. How do I know this? She says things like, “I really don’t like you.” I am mid-30s, have my own job, house, car, and depend on my parents for nothing. Every year for Mother’s Day I send expensive flowers and take her out for a fancy meal. Am I obligated to keep doing this?

A: No. It’s a little late for this year (I hope you took the day off and went to the beach), but for next year, and all future holidays, no, you are not obligated to take your mother out so she can tell you how much she doesn’t like you in a nice restaurant. Spend that time and money on someone who deserves and wants it.

Q. How can I teach a man to kiss?: I have recently started seeing a smart, funny, sweet, stable guy. We’ve been going very slow, which is great, as I want to really get to know someone before I get too physically entwined. However, after our first full-blown makeout, I have to say, he’s a terrible kisser. It’s like he draws his lips into his mouth whereas he should be puckering them. What the heck? He’s 35; how can he not know how to kiss? I am afraid this doesn’t bode well for other … ahem … skills. Any advice on this predicament?

A: He does know how to kiss; he just doesn’t know how to kiss you in the way that you like. This is one of those “speak now” situations—he can’t read your mind, and most people don’t spontaneously change their entire kissing style just for the fun of it without getting feedback. The only way to get him to kiss you the way you want to be kissed is to both tell and show him (try not to use the word terrible too often; go with “I like” and “I don’t like” instead). It will be a mildly uncomfortable conversation at the start, to be sure, but presumably he wants you to enjoy kissing him, rather than endure it, and it seems like a waste to dump someone you like a lot because his mouth is concave when it should be convex. That said, if you show him what you like and he continues to inhale his own lips when you two make out, you need to move on. Someone who has to be taught how to kiss may still be a perfectly wonderful boyfriend; someone who is either unwilling or unable to learn is just asking for suffering.

Q. Please take me seriously: I suffer from severe OCD and am under the care of a therapist and a psychiatrist. My particular brand is sometimes called purely obsessional, as my obsessions and compulsions take place entirely in my mind. As a result of this, and because I am relatively high-functioning otherwise, many people who are close to me seem to think I make too much of the disorder. I have been told to find a way to switch it off and asked why I was doing this (“this,” at the time, being sobbing with the psychological pain I was experiencing). How can I convey exactly how torturous this can be for me without appearing to simply complain and make excuses? It has nearly killed me and almost hospitalized me but for the intervention of my fantastic therapist, but I’m afraid to compare it with a “real illness” such as diabetes, which has been done in studies, for fear of derision and chastisement.

A: I want to give your friends and family the benefit of the doubt and believe they are simply unfamiliar with the seriousness of your condition, rather than unwilling to believe you when you tell them you’ve experienced profound psychological pain and despair. But your statement “[I] was sobbing with pain” and your question “How can I convey exactly how torturous this can be for me?” seem to paint a troubling picture. If the people close to you have seen you sobbing in distress, and their response was to tell you to “find a way to switch it off,” I’m deeply concerned about their ability to experience empathy and to recognize a crisis when they see one. The fact that you fear their derision and criticism if you were to try to explain your mental illness by comparing it with something better-understood like diabetes suggests to me that they’re not interested in understanding your experience but in getting you to stop talking about it.

You can ask your therapist or psychiatrist for some introductory resources for family and friends about the nature of OCD, about what therapies/medications do and don’t work, and why “just switch it off” is an ineffective suggested course of treatment. You are receiving medical treatment for a very real condition; you can explain but should not have to prove anything. The people who love you should want to believe and understand you; this is not difficult but is in fact a fundamental component of what love is. If, after receiving some basic prepping on your condition, the people who are close to you still try to make you feel like you’re just “complaining” or making excuses when you’re suffering mental and emotional distress, I fear that they do not have your best interests at heart, that they are more interested in seeing a version of you that’s easy to get along with than your real self, that they will would rather you suffer in silence than ask for help.

Q. Mooching sister: I have a sister who has borrowed approximately $25,000 from me. She is recently divorced and does not really like to work. She receives a modest alimony payment and works approximately 25 hours a week in retail. My sister and her ex-husband have never been smart with money. My sister and her ex went through bankruptcy in the past couple years. We both received approximately $120,000 in an inheritance when my mother passed away in 2010. My sister has spent all this money. I have spent some of mine on house repairs and improvements. In the past six months, I made my sister sign a statement saying she would not ask for any more money. It didn’t seem to help. Her ploy now is: “I need $400 for my electric bill” or “I need $600 to fix my car.” My ultimate nightmare is that someday she will knock on my door saying she has nowhere to live. I am the sibling who is more like her Depression-era parents. I pay all my bills on time and in full. I also work full time at a very decent-paying job that is stressful and approximately one hour from my home. I think I have a personality trait where I am “the caretaker.” 
How can I get my sister to stop being a mooch? Or get myself to say “No” to every request for money.

A: I read this letter expecting to have to answer the question, “How do I get my $25,000 back?” but you seem to have already resigned yourself to your loss and are merely asking for help in not giving your sister an additional $25,000. You must know on some level that your sister’s problem is not a genuine need due to lack of funds—there is, I suspect, no amount of money that would stabilize her. She will find a way to run through every loan, windfall, or second chance that comes her way until she is willing and able to make different choices. Every time you give her money, you’re helping her to put that day a little further off—which is to say, you’re not helping her at all.

Asking her to sign a piece of paper promising not to ask for money again is ridiculous and sad, because you both know that when she asks you for money, it works. It’s worked to the tune of $25,000, and it will continue to work until you are able to say, and mean, “No,” without explanation, without apology, without justifications, without argument. Just “No.” It may be worth spending a little bit of money with a therapist in order to figure out why it’s so difficult for you to stop bailing your sister out of her financial black hole and to devise strategies for sticking to your guns in the future.

Q. Blended family and in-laws: We are a blended family with children ranging from toddler to adult. My in-laws are particularly contentious and cannot seem to get beyond their narrow definition of what “real family” is. They continually, yet subversively, make a distinction between my children from a previous marriage and our biological child that we have together. We have explained our position, but they still find ways to divide us in conversation, i.e., “say hello to [bio-child’s name] for us!” without mentioning the others.
 My husband and I both stand united that this is not OK, but I need to know what I can say to put an end to this once and for all.

A: If you’ve already had a big-picture conversation about what you expect from them, you need to follow up when they try to cross the line with little digs like that one. They’re looking to see what little things they can get away with before you’re willing to call them out on it. If they say, “Say hello to [bio-child] for us,” you need to say, “Don’t do that. We have four kids, not one. We’ve already asked you not to act like our other children don’t exist.” Keep it short and simple. Your family isn’t a sectional sofa that you can break down and reassemble for someone else’s convenience.

Q. Re: Please take me seriously: I just wanted to offer the experience of someone who deals with a partner with long-term mental issues (clinical depression). I know that she suffers more than I can convey. Torture is a good word to describe it, and I want nothing more in the world than to help her through her disease. But it can be very tiring to come home from work, already having had a bad day, and find her crying and having a crisis. Sometimes, when fatigue and frustration set in, I can and have said something like, “Please, just stop crying.” I’m not proud of it, and I have gotten therapy, both alone and together, and she’s doing a lot better than she used to be. But I can understand how someone who loves a person with a serious mental illness can just feel tired and helpless, and even lash out, without wanting to do anything but help. I don’t know if that helps the letter writer or not, but her story made me think of it.

A: Thanks very much for sharing this. Part of me wants to hope this is the original LW’s situation. I understand everyone is limited and that even the most supportive friends and family members will sometimes be frustrated or a bit clueless about someone else’s mental/emotional health issues. It sounds like you’re a deeply loving partner who is also flawed and human and occasionally says insensitive things in the heat of the moment, which is understandable and a part of being human. What worries me is that the LW’s friends and family appear not to believe that her OCD causes her actual distress, and she fears they will mock and deride her if she tries to explain it to them. You once told your partner to stop crying out of frustration and exhaustion—you didn’t tell her she had no reason to cry or that her depression wasn’t real. There’s a serious and significant difference there, I think.

Click here to read Part 2 of this week’s chat.