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Get “Dear Prudence” delivered to your inbox each week; click here to sign up. Please send your questions for publication to prudence@slate.com . (Questions may be edited.)
Dear Prudie, When I was 9 years old, my parents divorced and both remarried. I lived with my mother and stepfather. When I was 17, Mom and Stepdad had to move to another city, so I moved in with Dad and Stepmom. My father’s new wife was a much younger and very attractive woman. The atmosphere was more relaxed than in my previous home. So much so that my stepmom (she’s about 15 years older) and I developed an attraction and started an affair. We were intimate about twice a month when my father was traveling for work. From Day One, we agreed that we would never tell my dad. I continued to see her during college and even after, when I came home for visits. My attraction waned because of distance, guilt, and because I started to see that she was a horrible person who was terrible to my father. I broke it off two years ago. Last month, Dad found out that she had cheated with another man (not me). They are in the middle of a vicious divorce. Last week, she called me and asked why I am so aloof. She told me that if I don’t convince Dad to concede on a financial matter, she will spill the beans about our affair. I feel like karma is giving me what I deserve, but I am scared. What is better: try to reason with this woman, even though she is irrational? Do her bidding in order to save Dad greater pain? Tell Dad everything myself, knowing that things will never be the same between him, me, and the rest of my family? I just want to do the best thing for him at this point, and I feel powerless.
Dear Karma, As Simon and Garfunkel said so eloquently about a similar situation: “ Koo koo kachoo , Mrs. Robinson.” Not only has this woman had an affair with her stepson and been multiply unfaithful to her husband, she is also an extortionist. The pain of extracting her from his life will be well worth it to your father. Now that she’s threatened you, it will be hard to ever feel comfortable with your father knowing she’s always fingering the pin on this grenade. None of your choices is good, but surely you want to be the first to let your father know you weren’t spending all your free time your senior year of high school in woodworking class. I don’t know what your father’s mental state or temperament is, so it might be best to deliver this news in a corner booth in a restaurant. That way, he’s sitting down and you’ll have some privacy, but if he snaps and starts strangling you, maybe the busboy can intervene. Tell your father you have been living with a sickening, shameful secret that has been a blot on your life. Give as brief an account as possible and emphasize that you were a minor when she seduced you. (It would help if you were also a virgin.) As horrifying as this revelation will be for your father, surely his lawyer will do a little happy dance when he or she hears not only this news, but that stepmom has been offering to exchange her silence for money. As for your relationship with your father, you’re right, it will never be the same. But at least now it won’t be based on deception.
Dear Prudie, One of my co-workers has lost all of his hair due to cancer treatments, and someone came up with the idea that we should all shave our heads in solidarity when he returns to work in a few weeks. A few guys have already shaved their heads, and they, along with several others who plan to follow suit, are laying one hell of a guilt trip on the rest of us to shave our heads, too. I have absolutely no desire to do so, and while several others on staff say they don’t want to, the guilt trip is working, and none of them wants to risk offending the co-worker when he returns. I don’t understand why he would feel any better looking at a dozen bald guys. I’ve already dusted off my résumé, but changing jobs won’t be easy thanks to the economy, and I’m not the kind of guy who just runs away when it’s time to take a stand. I don’t want a confrontation, but I didn’t pick this battle, and I fully expect that I’ll need to find a less toxic place to work because of my decision.
Dear Not Shorn, I understand the impulse behind the head-shaving gesture, and maybe your ailing co-worker will be both moved and amused. It’s also possible that he’ll feel uncomfortable and self-conscious. But surely he wouldn’t want every male in the office to be bullied into going along with the show of “solidarity.” You have every right to say, “What you’re doing is great, but it’s not for me” and to be completely left alone. I accept that there is a coercive group dynamic at work here, but your tone indicates a level of hostility that will only make things worse. Instead of engaging in battle, you have to be calm, pleasant, and firm. And unless your boss is wielding a pair of clippers, surely someone in charge would want to know that what should be a private choice is becoming an office-wide hazing.
Dear Prudie, I have been dating a fantastic woman for almost a year. We are both approaching 30. We moved in together a few months ago and are in the process of looking for a condo. She is wonderful, and, in the abstract, I hope to spend the rest of my life with her. But I have been engaged twice before, and both times the engagements ended miserably. These experiences have made me gun-shy about getting engaged again, especially after so short a time. But I may have made a mistake by telling my girlfriend all of this. She is very hurt by the fact that 1) my baggage with other women is affecting her life, that 2) I am able to say I want to spend the rest of my life with her, but don’t yet want to move forward, and that 3) with one of the two previous women, I proposed after only eight months of dating. Am I being unreasonable? Did I make a mistake by being honest about my baggage? I’ve hurt the person I love dearly but don’t know how to make her happy without, of course, proposing before I am ready.
Dear Not Ready Yet, That your two previous engagements ended amid bitterness and recriminations should have been information your girlfriend had before moving in with you. You seem to be in the habit of getting in deep while actually closing off the kind of openness that allows you to know someone deeply. Yours are exactly the kind of circumstances under which two people should not move in together. The problem is, she’s ready to get married now, but if you ultimately decide not to, she’ll be stuck in a condo with a guy who’s used up her most fertile years. It’s kind of pathetic that she’s jealous that one of your disastrous proposals took place after only eight months and feels that having clocked in almost four months more than that, she’s entitled to her own disastrous proposal. (But, of course, there’s nothing that makes a woman feel secure and loved more than being told you envision spending the rest of your life with her “in the abstract.”) That your response to all this is to wish you’d kept your romantic history a secret says that you haven’t learned much from your past mistakes. I suggest you cancel the condo plans; I even think the two of you would be better off not living together. If you feel you are heading toward marriage with her but need another year of dating, then tell her that, and see if that’s something she can be comfortable with. If you’re ever going to have a successful engagement, you need to get in the habit of talking honestly about what you’re feeling, and doing it before you make commitments you can’t keep.
Dear Prudie, I recently found out from a friend of mine that my mother-in-law has been posting pictures of me, my husband, and our kids on her Facebook page. She never once asked our permission or even told us about it. I’m not only annoyed but also concerned about my kids’ pictures, and who knows what information, being posted on the Internet. When I brought this up to my husband, he barely seemed bothered about it. I do not have the best relationship with my mother-in-law, and I want my husband to tell her to take the pictures down and stop posting them. Am I overreacting?
Dear Unwilling, You could start your own Facebook group: “My Mother-in-Law Posts Pictures of My Kids Without My Permission.” If Facebook has become a place for retirees to exchange snapshots of the grandkids, maybe it’s time it changes its name to Faceliftbook. Someone needs to tell grandma that if she wants to put pictures on Facebook, more appropriate ones would be of her and her friends passed out from too many Singapore Slings at their canasta tournament. I agree with you about your discomfort at having identifiable photographs of your kids floating around the Internet. You don’t want to get melodramatic about the danger, but such postings are forever, and it should be up to you as to whether you want to make them. Your husband should have a talk with his mother in which he praises her technological savvy but explains that once such images go out, you have lost control of them, and you’d prefer she show her friends how adorable your kids are in a more private way.
Photograph of Prudie by Teresa Castracane.
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Well, We’ve Entered The Fortnite Era At My House
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I walked into my son’s school a few weeks ago to pick him up. He was sitting with all his friends waiting for me by the door and immediately got up when he saw me coming. Clearly, he didn’t want me coming anywhere near his friends. I got the feeling he didn’t want anyone to know he was with me. I was right.
As he got closer, he whispered, “Mom, why do you have to dress like that? Everyone stares at you.”
“No they don’t. They are probably staring at you because you are so handsome,” I told him.
“I blend in. They aren’t staring at me. They are looking at you. Why do you have to wear dresses and high heels?” For the record, I was wearing the outfit below. The nerve, right?
I decided I wanted to try something with my teenage son that day. I asked him if he wanted to dress me for a little while. I told him he could pick out my outfits and I would wear whatever he wanted me to wear as long as he had an open mind and would listen to a few things I had to say about people and the way they choose to dress, so that’s what we did.
I wanted to talk to him more about the subject and why he was feeling the way he was. And by having him choose my clothes for a while I would better understand why he wanted me to wear certain things, and maybe he would understand why I like to dress the way I do and that, really, it shouldn’t affect him as much as it does.
This was his choice for the first day. He picked out a very casual, sporty outfit, and I loved it.
While I dress like this about half the time and like this look, it doesn’t always suit me. Sometimes I feel like dressing up more, so I do. When I asked my son why he picked this out, he said because I “blended in and didn’t look out of place.” In his mind, when I dress up, I look like I don’t belong. If he only knew how many women I saw throughout the day wearing suits and heels maybe he would have a different opinion.
Regardless, I told him nobody should be judged based on how they dress — not even your very embarrassing mother . Most people wear what they are comfortable in, what makes them feel good. It doesn’t matter where it came from because this isn’t how we judge others. We focus on how they make us feel, if they are kind, how they treat people. I told him judging people for what they wear is very transparent, and he will be missing out on a lot in life if he is going to focus on making friends because of what they wear, what they have, or what they look like.
If he is comfortable dressing in a way that makes him feel like he blends in, I think that is great. However, I want him to have the inner confidence to step out of the box if he wants. If he feels like wearing something, even though none of his peers are, I want him to feel like he can.
I also let him know what someone puts on their body isn’t an invitation, for him or anyone else, ever. And he should always take heed on how he looks at people, especially women. There is a way to look at a woman without staring or gawking. No matter how you see her, she deserves respect. I don’t care what she’s wearing.
I also want my son to realize just because I am a mother it doesn’t mean I have to dress a certain way. I loved the outfits he picked for me, and dress like that on my own accord often. But I also love wearing dresses, heels, skinny jeans, and trying out new trends because that is who I am, and who I was long before I became his mother. It’s not my intention to embarrass him. It is my intention to be myself, and him making comments or telling me he doesn’t want to go anywhere with me because of the way I dress is hurtful (as normal as it is).
A few days ago, I discussed these “lessons” I was trying to teach him with a friend and she told me he would “take all these lessons and bake them into a gentleman pie.” I really hope she is right.

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I’m not ready for him to graduate high school this June.
Writer, Blogger, and the mind behind My Dishwasher's Possessed!
Feb 22, 2017, 08:30 AM EST | Updated Feb 22, 2017
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Writer, Blogger, and the mind behind My Dishwasher's Possessed!
“Mom, this was the first time we ever saw a movie alone, just the two of us.”
I was watching my 18-year-old son, coffee cup in his hand, looking up at me between bites of his doughnut. We decided to grab a snack before heading home after watching “Hidden Figures.”
Wasn’t it just yesterday that I would walk him in his stroller to Dunkin’ Donuts? How could this man with the scruffy beard be the same toddler that I would hand-feed pieces of Munchkins to so he wouldn’t choke? And is it true, had we really never seen a movie, just the two of us?
“Yeah Mom. We usually are with Dad, or Lizzy and Peter, or Grandpa. This is the first time it was just you and me.”
The minute he said it, I couldn’t help myself from wanting a do-over. That’s it, he can’t be grown up, because we haven’t seen more movies together, just him and me.
It doesn’t matter that I’ve been an at-home mom his whole life. I got to see first steps, hear his first words, and watch almost every play, field day, and concert he took part in. We’ve had our share of mother-son dates. Who cares if this was the first time we saw a movie alone together? Kathy, get a grip.
I’ve had so much time with him. But selfishly, it doesn’t feel like enough.
I’m not ready for him to graduate high school this June and move on to college.
Yes, it was our first movie alone, but would it also be our last? It was just luck that we went to this one together. Usually he spends his weekends with his friends. But since he has been gone so much lately, he decided to take it easy and stay home with us. There’s no girl in the picture yet. Once that happens, I won’t see him much at all.
I’m ashamed to admit this, but I didn’t even really want to go with him. Or with anyone for that matter. I’ve been so stressed-out dealing with my daughter and her special needs as well as just the daily grind of being a mom of three that all I wanted was a few hours in a movie theater by myself.
I said a silent prayer of thanks that I listened to my better angels and said yes to a date with my son.
As my mind rambled on, I could hear Tom talking. The film moved him greatly. Of course he knew that racism and sexism existed, but it was different seeing it play out on screen. How is it possible that such abuse went on back then? Why is it that it racism and sexism still plague us today? He marveled at the strength of the women at the center of the movie’s plot and of the actors’ performances.
I had to keep willing myself to stay present because a part of me couldn’t get over that this young man who was so articulately discussing the film was the same kid who, as a small child, was so speech-delayed his preschool teacher told me she doubted he would ever lead a “normal” life.
I’ve watched him work so hard to overcome his dyslexia and do things that other kids took for granted. There were days when I wondered if I was up to the task of guiding this amazing person. Yet here he was, sitting in front of me, speaking of the history of NASA, and talking about about camera angles and set production.
I wish I could go back to that young mom who was terrified that her child would be OK. I would grab her and tell her that she should relax a bit and enjoy her child. It all worked out fine. He is getting ready to spread his wings and leave the nest.
Of course, knowing myself, I wouldn’t have listened.
So I snap out of my fog, and do my best to enjoy the moment I have. Sip my coffee and be glad for a date with my son.
This piece was previously published on Kathy’s site, My Dishwasher’s Possessed!
Writer, Blogger, and the mind behind My Dishwasher's Possessed!

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