Dear Prudence

A Face Not Even a Mother Could Love

How do I tell my boyfriend I think we’d have ugly babies?

Get “Dear Prudence” delivered to your inbox each week; click here to sign up. Please send your questions for publication to (Questions may be edited.)

Click here to read a transcript of Prudie’s live weekly chat with readers at

Dear Prudence,
My boyfriend and I are in a healthy and loving relationship, and we are beginning to talk about marriage. We both want the same number of kids at the same point in our lives. It is presumed that these will be our biological children. The issue is, I’m not sure that I would want to bear my boyfriend’s children. While he is incredibly intelligent and has a great personality, he is markedly less physically attractive than I am. We get occasional lighthearted comments from friends and family about the discrepancy. Having biological children has never been important to me, and I think adoption is great. I believe that he will be an amazing father and that our children, biological or adopted, would be bright and well-behaved as a result of good parenting. Should I bring these thoughts up with him? I think he would be open to the idea of adoption but would also be hurt by my rationale. At what point should we discuss this more seriously, and how should I tell him how I feel?

—Skinny Bitch

Dear Skinny,
You’re wise to avoid the potential tragedy of reproducing with your boyfriend: Your children could get his looks and your personality. Perhaps your boyfriend’s already got an inkling of how you feel because of the Leonardo DiCaprio mask you ask him to wear when you make love. And although Brad and Angelina are both fecund and support adoption, I’m not sure they’re going to agree to place any of their future progeny with you just to help you avoid the embarrassment of having a child who looks like your boyfriend. I’m trying to imagine how you initiate this discussion with him. Something like: “I look forward to spending the rest of my life with you. But when it comes to having kids, I’m sure that if we adopt we’ll have a better shot of having decent-looking ones than if I let you impregnate me with your hideous sperm.” That should go over well! What’s supposed to happen when you are in love with someone (who also happens to be intelligent and have a great personality) is that you discover, despite objective measures, that person is beautiful to you. Your boyfriend sounds like a catch, so maybe you should toss him back so that he has a chance to find someone who’s not permanently stuck in the shallow end.


Monstrous Mother-in-Law

Dear Prudence,
I’m in my late 30s, just finished a graduate degree, and recently started a temporary job that I like. I share duties with a younger woman also serves as a personal assistant to our boss. Over the past few months, she’s gradually revealed that the boss (a man in his 40s) has been using her as an emotional outlet, sharing his insecurities, fears, and early traumatic experiences with her. This situation has been so taxing for her that she found a new job. I’ve accepted her job since it means a permanent position. Professionally, it’s a treat to work alongside my boss, who is very knowledgeable and puts a lot of effort into his work. However, I started noticing that he expects me to substitute for my former colleague as his new “handkerchief” to weep into. Of course, I am capable of occasional sympathy, but I’m not prepared to become my boss’s psychoanalyst. I would prefer to maintain a professional distance and save my emotional support for my husband and child. How do I tactfully spell this all out for my boss so that I preserve a good working relationship and don’t offend him?

—A Cold Shoulder

Dear A Cold,
You are in a delicate situation since you like and want to keep your job, but the person who decides how much you like it and whether you keep it is a psychological wreck. Maintaining your professional distance is obviously the right and necessary thing to do. But when you work for someone unbalanced, not feeding his emotional needs does potentially put you at risk of him turning on you. Your difficulty is compounded by the fact that he’s good at his job and therefore valued by the company. You need to have a series of stock phrases that convey your concern but close off further confession: “It’s only human to doubt yourself sometimes.” “In this economy, everyone can’t help but second-guess themselves.” “Your childhood sounds difficult and painful.” Then, when you’ve delivered one, immediately change the topic back to the work matter at hand. If he tries to persist with the psychoanalysis, you have to politely turn away such further conversation: “If you really are that worried about this decision, maybe you should discuss it with someone else in the company.” “I’m afraid I’m not the right person to talk to about such personal matters.” It might even help to role play this with your husband, so that when your boss starts moaning, you have practice maintaining a neutral, unflustered tone. If you’re good at your duties and don’t allow yourself to be drawn into his drama, let’s hope he will turn to more suitable sources of solace.


Dear Prudie,
Since graduating from college several years ago, my younger sister has adopted what you might call an alternative lifestyle. She lives in our parents’ basement, works part time at a fast- food restaurant, and spends the majority of her time protesting for various causes. I have been sympathetic until recently, when she adopted the freegan lifestyle. Freegan means that she goes out in the middle of the night to dig through dumpsters behind grocery stores and food production plants. Her stance is that perfectly good food is being thrown out for cosmetic or other bogus reasons. This weekend, I visited my family, only to find the freezer full of expired health drinks and bagels and the cupboards stuffed with other expired or damaged items—including health-food bars that were recalled because of potential salmonella poisoning. I was so grossed out, I wouldn’t eat anything without first inquiring about its origins. My sister pays no rent and has no expenses, and my parents would happily buy her any food from the store. I have tried to encourage my parents to put their foot down about her bringing garbage into the house to no avail. Their opinion is that I am the one being unreasonable. Please help!

—Gag Me

Dear Gag,
Since I recently spent the wee hours driving the porcelain bus because of some toxic stuffed peppers (which I paid for!), I am sympathetic to the roiling in your stomach at the thought of eating food rescued from the dumpster. As long as your family’s cuisine of choice is not Italian or Chinese but “Recalled by the FDA,” when you’re visiting and mealtime comes around you should make a pitch for supporting the beleaguered restaurant industry. I think your distress is about more than your digestive system, though. It’s driving you crazy that your parents, instead of encouraging your sister toward self-sufficiency, are indulging her to the point that they are potentially endangering their own health. But take note that the harder you push on this, the more they rush to her defense. So don’t give yourself a stomach ache over your family dynamics. Instead, just be glad you’re not living in the basement, too, and consider brown-bagging it the next time you visit.


Dear Prudence
I am a 14-year-old girl who’s a freshman in high school. In eighth grade, I was in all the same classes with an odd kid named “Larry.” He often said off-topic things in the middle of class and made inappropriate comments. I was nice to him, so teachers paired me with him for every group project. He developed a huge crush on me and gave me a card on Valentine’s Day. I told him I liked him only as a friend, and everything seemed fine. Then this year he asked me out. I told him no, but he is totally oblivious and won’t take no for an answer. He asks me to go out with him in embarrassing places, like in class, and hugs me in the hallway, which makes me feel uncomfortable. My friends say he’s harassing me. I don’t want to embarrass him by making him go to the guidance counselor or talking to his parents, so what should I do? My parents know all the details, but I don’t want them to get involved because I want to learn how to deal with an uncomfortable situation on my own. How do I make Larry stay away from me? I’m not even interested in a friendship with him anymore.


Dear Uncomfortable,
It is great that you were kind to Larry—he has problems that keep him from understanding normal social interactions, and he probably hasn’t had much compassion from his classmates. Also admirable is your desire to handle this yourself. But how to deal with unwanted advances from someone who doesn’t understand “no” is a difficult problem even for adults to solve. You’re only 14, so for your sake, and for Larry’s, you need adult intervention. Tell your parents you can’t handle this anymore, and you would like them to go with you to talk about this with the guidance counselor. This is not about getting Larry in trouble; he needs to learn now how to restrain himself so he doesn’t get into bigger trouble later on. The school should take action immediately to help Larry understand that he must stop asking you out and touching you. If this doesn’t get better right away, keep speaking up to the adults who should be making sure you feel comfortable at school.