Dear Prudence

A Family Affair

I slept with my stepmother for years. Should I tell my dad?

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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.

—Karma’s Bitch Boy

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 Prudence Video: Flirting Husband

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.

—Not a Shorn Sheep

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.

—Not Ready Yet

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?

—Unwilling Participant

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.