Dear Prudence

The Malevolent Mentee

Prudie advises a letter writer being blackmailed by a former intern.

Emily Yoffe.
Emily Yoffe

Photo by Teresa Castracane.

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

Emily Yoffe: Good afternoon. I look forward to your questions.

Q. Emotional Affair and Blackmail: I’m in the middle of an intense emotional affair at work. I am separated, his marriage is on the rocks, but nothing has happened beyond hand-holding. We get an incredible amount of support from each other and thought no one at work noticed. The issue is my summer intern: She did notice and is now threatening me that I have to write her a letter of recommendation better than the one I did or else she will “tell.” She did an OK job but was not the best or brightest, so I wrote a B-plus recommendation. She confronted me and mentioned she knew everything. So should I write an even more enthusiastic letter or stand my ground? I really feel like I haven’t done anything wrong with my colleague but don’t want to deal with any awkward questions.

A: First of all, let me assure you that your intern doesn’t have special powers to see into the human heart, but everyone at work has noticed. So now you and your pal have been put on notice that you have to seriously cool it. He is married. While you two are entitled to be friends, holding hands around the periphery of the office, having intense conversations in the hallway, etc., is unprofessional and, as you’ve seen, bound to catch up with you. But the good news is that there’s really nothing to tell. Your intern was an OK employee, but she’s definitely an unskilled blackmailer. In response to her crude threat you should do a couple of things. One, create a time-stamped file and document everything this little extortionist has done. Next, go to HR and report that you are being threatened by a former intern. Say her proposal is to get a better recommendation out of you in exchange for keeping quiet about your private life. Explain, however, that she has misconstrued a friendship with a colleague and there is nothing for her to reveal. Ask that HR, or your company’s attorney, let the intern know about the consequences of blackmail. Let’s hope this possible little sociopath realizes she’s heading down the wrong path. But be prepared she may really be off her rocker and could escalate things by making false allegations. Your own documentary evidence of her treachery will make a powerful case against her.

Q. Ex-Husband Abandoning One of Our Three Kids!: My ex-husband “Greg” and I share custody of our three children. Recently Greg told me he no longer wants to see our eldest daughter, “Jaime,” who is 11. Although Jaime isn’t biologically Greg’s—I had her before we met—he’s raised her from infancy and adopted her, and is the only dad she’s ever known. (Greg’s family’s horrified by his decision; she remains their granddaughter/niece/cousin.) Greg only wants to take “his” kids on the weekends. He says his decision isn’t about child support or watching three active kids on his own. He just “has no interest” in continuing to raise Jaime. I’m lost as to what I should do, and part of me wants to fight for sole custody. I know that’s not fair to my younger kids, though. Greg refuses family counseling, so what do I do now?

A: This is one of those things that makes you hope maybe Greg has a tumor and once it’s removed he will stop being a monster. Jaime is his child, so his sudden rejection of her is grotesque. Since you know his family is horrified, perhaps you can have a powwow with them to try to address this. Maybe there’s someone who Greg respects who can explain to him that by spurning Jaime he is putting at risk his relationship with all his children. If this fails, then talk to your lawyer about Greg’s fitness. You’re right, you don’t want to strip him from the lives of his children, but the ugliness of his expressing that their big sister is no longer his has to be dealt with. You also should speak to a family therapist because you will need help negotiating these psychological shoals.

Q. Strangers’ Comments to Smoking Pregnant Women: My boyfriend and I have been dating for over a year and have discussed a future together, including marriage. I was horrified to learn, however, that he thinks it’s appropriate to approach a smoking pregnant woman to remind her of how much harm she’s doing to her fetus. He’s only done it once, but philosophically he believes it’s the right thing to do. I believe that pregnancy does not make it acceptable for strangers to comment on a woman’s body or behaviors, and that this is a topic that should be between a woman and her doctor. He’s surprised I don’t agree with him, considering my strong anti-smoking stance. His opinion is deeply offensive to me and we got into a huge fight about this. Although we both consider ourselves feminists, he doesn’t think this is a feminist issue. Things got so heated that it’s threatening our relationship, which maybe says more about how we argue. I’m just really having trouble getting past this. Help!

A: The thing about these public health announcements is that the person who smokes or drinks while pregnant is either so ignorant that the warnings of a stranger won’t do any good, or she knows it’s harmful and is doing it anyway. I understand where each of you are coming from. I assume you don’t take such an absolutist stand that you wouldn’t consider intervening if you saw a mother abusing a child. I’ve gotten many letters about people who have observed strangers in subways or on the street hurting their children and wondered what to do. (I’ve suggested that they weigh whether what they’re witnessing requires the intervention the police, and if so, making that call.) What your boyfriend did likely had no effect on the mother, was intrusive, and was embarrassing to you. But since you say this has occurred only once, it doesn’t sound as if he considers himself the moral police of pregnant women. I think you actually zeroed in on the real situation, which is that you two can’t agree to disagree—even strenuously—about a subject. So now your entire relationship is tottering. So let’s say you break up and someone asks you, “You seemed so good together. What happened?” And you answer, “He went up to a pregnant woman who was smoking and told her she was harming her fetus.” Consider whether that makes you feel righteous or silly and proceed accordingly.

Q. Re: Ex-Husband Abandoning One of Our Three Kids!: My husband (now late 50s) was adopted by his mother’s second husband when he was 5. Their three biological kids grew up with him, and he called this man his father. His mom and adoptive father went through a horrific divorce when he was 17. His adoptive father very clearly favored “his” kids, inviting them on world adventures to which my husband was excluded (among other things). Then at some point his adoptive father decided he didn’t want to see my husband any more. Gave him no explanation, and in fact put his siblings in the middle by instructing them to not let my husband know when he was visiting. Even as an adult this was extraordinarily painful and also caused a rift between him and his siblings. This is deeply painful stuff, and this type of rejection by someone who you think of and called a parent (regardless of biology) never goes away. My husband has been helped through therapy, and he says that he thinks of his adoptive father as dead.

A: What an awful story. Reminder to people who adopt children: They’re your children, period. I appreciate your telling this, because you’re right, this kind of rejection is going to echo through someone’s life. I hope Greg reads this and decides not to destroy everyone’s relationships.

Q. Cheating Co-Worker: I became friends with a co-worker, and then I met her boyfriend and we had an instant connection. He left her for me. We’ve been together for six years (married five with a newborn son). The dilemma is that she and I still work together. I know she has moved on but I am still faced with constant guilt over this. What should I do?

A: You’ve moved on to marry the guy and have a kid, and you know she’s moved on. At this point she likely thinks everything turned out for the best. You don’t say she freezes you out, undermines you, or does anything but act professionally. If you can’t get over what you did, then see a counselor for some short-term therapy to come to terms with this, and be able to see your husband’s ex without feeling overwhelmed.

Q. Card Etiquette?: I broke up with my boyfriend of six years a couple months ago. The breakup was bitter, although I honestly think he’d been trying to get me to initiate it so he wouldn’t have to. My question—do I need to break up with his family as well or can I continue to send holiday cards/gifts to his parents and daughters (and, if so, should I get his approval before sending anything to his daughters)? They are all quite lovely, and, honestly, I probably would have broken up with him sooner if not for my relationship with them.

A: You had a relationship with his family because of your relationship with him. But your fondness for these people is also independent of your romantic travails. I once had an ugly breakup with a boyfriend whose mother I cared for very much. We exchanged Christmas letters until her death. If you were in the habit of giving gifts to his children and exchanging cards with his parents, I think continuing this is just fine. You want to strike the right balance of not appearing to try to one-up him by giving something extravagant, and in your note you don’t want to get into the reasons for your breakup. You can say something to the effect that you are thinking of them fondly this holiday season. That even though you and Roger are no longer together, you will always appreciate how they welcomed you into the family.

Q. Son Who Hates to Read: I have a son who hates to read. I had him tested for possible disabilities (dyslexia, difficulties reading text on a white background, etc.). There is nothing wrong with him, except that he would rather have a root canal than read. This antipathy affects not only his academic performance, but also creates tension with my husband the bibliophile who cannot fathom anyone not loving to read. Any suggestions?

A: What does your son love to do? Is he an athlete, a musician? Is he great at working with his hands? I am a compulsive reader, one of those people who would read the fine print on the cereal box if nothing else was available. But not everyone loves to read. For some people it’s just a drag, and there’s nothing wrong with them. True, this perspective makes school very hard, because school is text-based. So knowing that this is the case, you need some support for your son, and maybe some technological innovation. It could be that he has an easier time absorbing information aurally. Maybe some of what he’s supposed to read, he can listen to, for example. Talk to a learning specialist about this and other ways to help a non-reader succeed. You should also encourage him in ways he can feel successful at school. Maybe he gets into theater, or studio art. Your husband needs to be in on the meetings with the professionals so he can understand that his son is not here to recapitulate his life, but to make the most of his own.

Q. Re: Approaching Smoking Pregnant Women: I was outside my office building having a cigarette one day, when a “gentleman” walked by and looked me up and down and said … “smoking while pregnant, nice work” and walked away. The thing was … I wasn’t pregnant! I gained a lot of weight even postpartum, was wearing an admittedly unflattering dress, and clearly I looked pregnant. I was mortified and humiliated.

A: Great point! Assuming someone is pregnant can be fraught with peril.

Q. Children Using Technology: I allow my 3-year-old 30 minutes maximum a day on my iPad. We set a timer, which can be paused and then restarted, but once the 30 minutes are up it rings, and he knows it’s time to put the IPad away. Recently at a meeting at his preschool, I was berated by another parent who said I was ruining my son for allowing this, because I was killing his ability to be creative and think. I did not answer, as I wanted to avoid escalating the situation. Am I really such a horrible parent for allowing 30 minutes a day on an iPad?

A: Fortunately, Hanna Rosin has come to your rescue. You must read her Atlantic story, “The Touch-Screen Generation,” which will totally reassure you about your son’s screen use. Once upon a time, parents railed that the evil new technology, books, would destroy the next generation’s ability to remember and recite long sagas (well, they were right). Every new innovation brings such condemnation, then people come to realize they can’t live without the technology. Whatever replaces tablets will surely be described as destroying young minds’ crucial ability to work on tablets. You are seriously limiting your son’s tablet time, but there’s lots of great stuff to be discovered on an iPad (not to mention the relief of sticking it in your son’s hands and being able to make dinner). If you’d mentioned your son loves peanut butter sandwiches and milk, you probably would have gotten berated for poisoning him with gluten, nuts, and dairy. Just ignore the fanatics. 

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

Discuss this column with Emily Yoffe on her Facebook page.

Check out Dear Prudence’s book recommendations in the Slate Store.