Dear Prudence

Term’s Up

Prudie advises a letter writer whose son by a first marriage is a waste of tuition money.

Mallory Ortberg
Mallory Ortberg

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 voicemail of the 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! Let’s chat.

Q. Give up: I have four children—a son by my ex-wife and three daughters with my current one. My son was raised by his mother and completely indulged by her. It has always been a huge source of conflict between us. My son graduated high school a happy C-level student but was able to get into a good school. I paid for his first semester. He failed all but one of his classes. I wanted him to come back home and try community college rather than continue to waste my money. We all fought but came to an agreement that if he actually buckled down and got decent grades I would continue to do support him. This spring he seemed to do so. He sent me proof with his tests and essays. I really prayed he was turning his life around. Then over spring break, he got drunk, stole his grandmother’s car and destroyed it. We did not file charges but told my ex and my son that this was it in terms of financial support. My wife and I have worked long and hard to give all our children a chance at a good education and a better life. My daughter will be graduating in May with a 4.0 and a partial scholarship to an excellent school across the country. Her sisters will be graduating in the next two years. My son will have wasted over $25,000. I can’t afford to throw good money after bad. My son responded by calling my wife and his sisters “bitches” and cussing me out. My ex repeatedly tells me how much of a failure I am as a father and how I “threw away my only boy.” My wife told me I have done all I could do and more than I should have. Part of me agrees with her but part of me wonders. I love my son and I continue to love my son but I feel like I have failed him. I don’t know what else to do now—he is a grown man and has taken every chance life has given him and pissed it away. What do I do with this? Is there anything I can?

A: It is possible that you have, in significant and unalterable ways, failed your son, but it does not necessarily follow that you are now obligated to continue to pay for his schooling if he is incapable or unwilling to discharge his responsibilities as a student, nor does it make you an irredeemable “failure” of a parent. If you two are ever going to be able to honestly discuss your limitations as a parent, or the pain he may have experienced as a child, those conversations will have to be predicated on basic respect, not by calling your other children, who are entirely blameless, “bitches.” Your offer to pay for community college was a reasonable one, and you are not being unduly cruel or vindictive in withdrawing financial support given his recent destructive behavior. You may not have been as present a father as you could have been in the past, but you are decidedly not “throwing him away” now, and if your ex-wife continues to accuse you of doing so, feel free to respectfully but firmly end the conversation.

Consider what you are willing to do for your son now, whether that be meeting to discuss your relationship, attending counseling sessions together, or helping him seek treatment. You can offer him a new kind of support as he continues to move into adulthood and remain available whether or not he seems interested in it at present. You can take responsibility for your own limitations and mistakes as a parent without taking responsibility for his current choices—you are not the reason he stole and crashed his grandmother’s car. If he continues to lash out or blame your other children for his current problems, you’re not obligated to act as a punching bag. Let him know the door is always open if he wants to reconnect, but that you’re not going to give him any more money or let him insult the rest of your family. This is painful but necessary work—you’re not going to fix the mistakes of the past by letting your son mistreat you and your other children now.

Q. Handouts: Yesterday my boyfriend’s mother offered to pay for some classes in cake decorating for me so that I can further my experience in baking to get a better job. I’m unemployed looking for a bakery job right now, which is why she offered to pay, and she wants me to pay her back by doing housework for her over the weekends. As much as I would love to take this opportunity, our relationship has been strained because of the circumstances of how her son and I came to be. I’m scared that she’ll pay for the classes and then somehow hold this over my head. I’m afraid to talk to my boyfriend about this because I don’t want to stress him out because it is his mother. Do I take hold of this opportunity and deal with what may come with her or do I find a way to pay for it myself?

A: If you’re suspicious that this quid-pro-quo-not-quite-a-gift is going to come with serious strings attached, you shouldn’t accept it. If you think your boyfriend would be emotionally incapable of even discussing his mother’s offer to you, then you definitely shouldn’t accept it. If your boyfriend’s mother wants you to become her unofficial housecleaner in exchange for cake-decorating classes, you should run in the other direction. Better to find a job at a bakery washing dishes and ask for on-the-job training, or look for a baking apprenticeship, than to enter into a housecleaning-for-baking-classes exchange with a woman you have a strained relationship with. Thank her for the offer, but look for other, smaller ways to establish a better rapport with your boyfriend’s mother.

Q. Renting to family: My parents had an old beach house that was in danger of foreclosure. Rather than lose this place that has been in the family over 15 years, my husband and I bought it from my parents. At the time, we asked my siblings if they wanted to go into this with us. They declined. We paid off the house and invested over $10,000 to update the beach house and rent it out. Frankly it was a good investment because the area exploded and during peak times we can get over $2,000 a week for it. My family has been over many times in the five years since we fixed up the place. We spent several holidays together but always with us. Now my niece wants to come down with a pack of her college friends and stay for the week right in the middle of summer. We had already rented the beach house out until the end of August. I told my niece her dates didn’t work and offered her the last dates for $500. This caused a ruckus. My sister called me to yell at me for daring to charge family, that the beach house apparently belonged to everyone, and how greedy I was being. I told her point blank the beach house was mine. We were the ones who put money, work, and sweat into the place. Everyone else was willing to let it go to the bank. At this point everyone in the family is involved. My mother wants peace, two siblings are on my side, one on my sister’s, and my husband is this close to wanting to sell and buy another beach house to spite the lot of them. Is there anything I can do to end this?

A: The beach house does not belong to everyone in the family; the beach house belongs to you and your husband, primarily due to the fact that you purchased it and the rest of the family did not. You offered your siblings a fair opportunity to purchase the house jointly and they declined. You offered your niece a reasonable price for a vacation rental—less than $100 a night, less still if the cost were split evenly among her and her friends—and she declined. I don’t advise you to purchase another home out of spite, but there’s no reason for you to apologize or offer your relatives free use of your beach house. Stay calm, but hold your ground, and if you continue to receive furious phone calls, feel free to end the conversation: “We invested a lot of money into this property, and we rent it out when we’re not using it as part of our income. If anyone would like to stay at the beach house, we’re happy to offer a reasonable price to offset the cost of upkeep and cleaning, but it’s not available for free. If you’d rather stay elsewhere, we understand, but the matter is closed.”

Q. The agony of art: My wife and I recently moved back to the city where I went to school and I have reconnected with an old friend “Bill.” “Bill” is married to “Margie,” and we often have dinners as a foursome. Margie is a wannabe novelist who spends a lot of her time speaking about the Agony of Being an Artist. The first time we went out she literally said “Being a Writer I have one less layer of skin than other people.” The thing is Prudie, I am, if not a Writer, then certainly a writer. I’ve written five books for a well-known publisher under a female pen name and they are selling well (think vampires and bit of romance). When the kids were little, I used to write at the kitchen table. Now I get up early and write before going to work. It’s fun and I enjoy it. There is no agony in my world. The problem is my wife. She says things like. “Next time we are out with Bill and Margie I am going to take a bag of your books along and if that little twit starts agonizing about being a writer I’m going to take them out and bang them on the table.” How should we deal with my good-natured friend and his Tortured Artist wife?

A: If your wife were to bang your books on the table, I have no doubt that Margie would respond not with, “My God, being a writer isn’t that difficult after all—I’ve been making so much extra work for myself!” but “Well, you’re not an artist like I am, merely a competent journeyman; this is why your pedestrian little romance novels don’t keep you up at night, tearing out your hair and rending your garments. How lucky you are to have the soul of a grocer and not a sensitive aesthete.” The best response to Margie’s ceaseless groaning is cheery disinterest: “I’m sorry to hear that! Hope things get better soon. What else is new with you two?” If it becomes absolutely impossible to deter her from making her miserable work life the sole topic of conversation, you can make more explicit requests to change the subject; if that doesn’t work, find other couples to have dinner with and scale back on your interactions with Bill and Margie. Let her miserable sonata fade into the background of your life, rather than buying front-row seats three or four nights a week.

Q. Re: Handouts: I got a part-time job at a grocery store bakery, and I was taught how to decorate the cakes there. It’s a good beginning step toward a better job, and you get paid.

A: Helpful point!

Dear Prudie: Is it inappropriate for me to go to the funeral for my high-school ex’s mom?

Hear more Prudence at

Q. Third wheel, two faces: I’ve been close friends with “Sara” since we were 12. Our friendship survived difficult adolescent times for both of us, including a painful crush I had on her while still in the closet. The crush is long gone, we’ve both become happy and successful, and we’ve built a healthy, supportive adult friendship. She came to visit me recently, and I introduced her to my good friend “Brian,” thinking they’d get along. Sparks flew, they’re now dating long distance, and I’m thrilled because they’re both so happy about it. The problem is Brian. He’s usually one of my kindest friends, but he’s suddenly become rude to me, to the point of being cruel. He made fun of my teenage struggles with my sexuality, which I told him never to do again. He apologized but is still making cutting remarks about everything from the quality of my Ph.D. work to how he “has to” stay friends with me because of Sara. I think he’s threatened by my long friendship with his new girlfriend, but I don’t know how to make him stop treating me this way. How do I talk to him?

A: “Brian, you’re normally a good friend to me and that’s why your behavior over the last few months has come as such a surprise. You’ve started making cruel comments about my sexuality, the quality of my work, and the fact that you think of our friendship as something you ‘have to’ maintain, rather than something you enjoy. What’s going on? Can you explain what’s changed, and why you would say these things to me?” If he’s able to acknowledge his behavior and offer a genuine apology, as well as a vision for how he’ll behave differently in the future, you two may be able to see your way forward. If he claims not to know what you’re talking about or offers a series of flimsy excuses, your friendship may already be at an end.

Q. The slow fade: I grew up in a chaotic household with emotionally abusive parents (neglect, gaslighting, manipulation, lying, outbursts, tantrums). I have done a lot of work as an adult to work through this, including moving far away from abusive family members and seeing a mental health professional, and have set boundaries on how much time I spend with or contact them. I recently traveled to my hometown for the first time in over a year for my cousin’s wedding, and it went poorly. It was very triggering for me, and I had a panic attack at the thought of having to go over to their house one more time before I left. My partner and best friend convinced me not to go and helped me delicately excuse myself from the visit. Despite having a loving, supportive partner with me, it was still incredibly challenging being there. I am now wondering whether or not I want to keep these people in my life, even with limited contact. I know you have given some people the go-ahead to cut abusive people out, but what do you say about doing the slow fade out? Do I owe them any explanation for why I don’t want them in my life anymore, or can I just slowly disappear while focusing on my happy life elsewhere? For what it’s worth, any attempt at talking about the abuse has been met with explosive tantrums on their behalf—screaming, crying, slamming doors.

A: You can absolutely fade out on your abusive family members. Anyone who makes a habit out of screaming and slamming doors has already declined to participate in civil, honest conversation. You do not need to invite them to continue to belittle you, and you know that trying to explain why you don’t want to speak to them would only lay the groundwork for additional abuse. Feel free to be a little busier than usual when they call, and don’t feel like you’re being dishonest or denying them the opportunity to change. Your parents have already demonstrated that, as they are now, they are incapable of hearing anything you have to say about their abusive behavior and responding with anything resembling rationality or open-mindedness. The kind of conversation that you cannot imagine having with them is already impossible under current conditions. Fade out on them for as long as you need to, even if that means the rest of their lives. Focus on your own health and your happy life, and don’t look back.

Q. Sister loves dog more than baby: My sister is always making comments like “I like my two-legged baby, but I love my four-legged baby!” and lavishing her dog with attention while complaining that her 11-month-old daughter doesn’t appreciate her. Compounding matters, the dog is an absolute jerk. Snaps at people, defecates indoors, knows no boundaries. My sister mocks her baby when she cries and keeps her confined in a play yard most of the time. Meanwhile, she spends thousands of dollars and a ridiculous amount of time entering her dog in competitions. The baby is brought along but kept in her carrier the whole time. My niece’s basic necessities are being met, but she’s treated like a second-class citizen next to the dog, because “the dog was here first … and she loves me.” Is this lack of bonding with her baby some kind of postpartum depression? How can I suggest she get help?

A: This is deeply disturbing behavior; I don’t know enough about postpartum depression to judge whether or not this is a sign that your sister is unwell, but your impulse to tell her she needs help is a sound one. It’s heartening that your sister’s baby is getting her basic needs met, but if she’s spending most of her time locked up in a playpen, she’s likely not receiving anywhere near the sort of touch and attention she needs. To whatever extent you are able, whenever you’re with your sister, try to be as affectionate and attentive to her child as possible. Speak to your sister about your concerns immediately—tell her you’re deeply concerned that she mocks her baby for crying, that she resents an 11-month-old for not “appreciating” her, and that she keeps her in a playpen most of the day—and encourage her to make an appointment with her doctor to discuss the possibility of postpartum depression. The dog is a bit of a red herring; the way your sister treats her child is upsetting enough on its own, and it sounds like she’s the type who would bristle at any mention of her dog’s elevated place in the family. The most effective strategy, I think, is to focus on your concerns about the baby without triggering your sister’s protectiveness for her dog.

Q. Delay delay delay: I have been engaged for going on three years in May after dating for 11 years. After two years of waiting for a date I finally threw my hands in the air and said “no more” and pushed all the planning to my boyfriend. The problem seems to be that he wants his family present for this, but they are nonresponsive to coming out here for this event (they live in Chicago; we live in Montana). They all go on vacations every year and in the 20 years that he’s lived here they have been here three times. I’m a little tired of waiting and my son graduates from college next year and I don’t want to cram all these events into one summer. How can I get him to finally get with his family and explain to them that he wants to get married here and he wants them here and it really hurts his feelings that he’s been in all his siblings weddings but they won’t participate in his? It seems to me that if he asks they should show up, right?

A: If you would like to get married this summer, then you should set a date with your fiancé. Then send invitations to his family members; if they seem undecided over whether to attend your wedding or take a vacation somewhere else, you can encourage him to have a conversation where he stresses how important their presence would be to him. It’s not, however, a conversation you can force him to have if he’s not interested in it, nor is it one that you can have for him. You two have been together for 14 years, and people get married without their entire extended families present. If it’s important to you to get married this year, then make it a priority, with or without his family present, and decide whether you are willing to end the relationship if you believe your boyfriend is dragging his feet because he doesn’t really want to get married.

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