Dear Prudence

Diamonds Aren’t a Girl’s Best Friend

My ex is blackmailing me for sex. How can I get out of it?

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.)

Got a burning question for Prudie? She’ll be online at to chat with readers each Monday at 1 p.m.  Submit your questions and comments here before or during the live discussion.

Dear Prudence,
I’m in my mid-20s and in a wonderful relationship of two years with a man I love more than I thought possible. Before him, I was in a terrible relationship with an older man for almost four years. That relationship was primarily sexual. It was also emotionally and sometimes physically abusive. I got counseling and thought I was over it. My grandfather, whom I was very close with, died recently, and I was unable to travel to my family’s home at the time of his death. My boyfriend was also out of town. I sought comfort in the worst possible place, with my ex. I feel terrible and will never cheat again. That night, I lost a pair of diamond earrings my mother had given me. I was overjoyed when my ex texted me that he found them. I said I’d pick them up, but his condition was that we have sex. I refused, and he said that he would mail them. It’s been over a month. I haven’t gotten the earrings, and he hasn’t responded to calls, texts, or e-mails. The earrings have sentimental value, but I don’t want to compromise myself or my relationship for them. What should I do?

—Earring Dilemma

Dear Earring,
Talk about conflict diamonds! Let’s get this straight: Your gem of a boyfriend is out of town at the time of the death of your beloved grandfather. So you ring up your louse of an ex and have sex with him as a form of grief counseling. Although I’m strongly in favor of ending abusive relationships, part of me thinks you and the louse are the better-matched pair. What you do about the earrings now being held hostage is peripheral to the fact that you apparently lack both morals and impulse control. I’m not always in favor of confessing stupid, never-to-be-repeated one-night stands. But your ex is the kind of manipulative creep who sounds capable of sending the earrings, along with a note about how they came into his possession, to your boyfriend to pass along to you. It will be hard for you to ever feel at ease in your current relationship knowing that your ex has a string of texts and e-mails proving your infidelity. I think you need to come clean with your boyfriend, which means you run the risk of losing him along with the earrings. But surely your relationship will be on ice anyway if your infidelity comes to light. As for the earrings, bravo that you’re declining your ex’s offer to return your rocks in exchange for getting his rocks off. Your most effective course may be to have a lawyer draft a letter to your ex outlining the legal issues raised by his holding your property in exchange for sex. If that doesn’t shake the earrings loose, you have to decide whether you’re willing to pursue further legal action. And although it probably won’t provide much viewing pleasure, the classic movie The Earrings of Madame De… uses a pair of diamond earrings to demonstrate the consequences of being careless about love.


Dear Prudence: Crush on My Boss

Dear Prudence,
I am the mother of an extremely intelligent 17-year-old son. He tests off the charts, takes advanced placement classes, and wins all kinds of academic awards. Sometimes it is hard for me to believe he’s my child because I’m of average intelligence. I went to a run-of-the-mill state college and didn’t finish my degree. I have a good job and I am very good at what I do. My problem is, I feel so inferior to him that I’m loath to have all but the most basic of conversations. His passion lies in areas that I am clueless about (biochemistry, for one). He’s also politically savvy, but on the other end of the spectrum from my views. He is respectful, but I get the impression that he really has to dumb it down to have a conversation with me. I know he gets frustrated when I don’t follow what he’s talking about. He’ll be going off to college next year, and I’m worried that once he’s away, he’ll be around people more in line with his intelligence and views, and our bond will be forever broken. Any suggestions—or is this just the natural progression of things?

—Average Mom

Dear Average,
If you were the brainiac and your teenage son of average intelligence, believe me, he would still be frustrated with your obtuseness. Your son sounds like a spectacular kid who’s still willing to engage with you, despite the fact that you couldn’t possibly know as much about anything as he does. There’s a game show called Are You Smarter Than a Fifth Grader?; the premise is to humiliate adults over their lack of basic knowledge. Unless you dabble in biochemistry yourself, there’s no way you’re going to be conversant with this passion. But you can ask your budding scientist to explain what’s exciting about this field, what breakthroughs he hopes to work on. It’s encouraging that you two can engage in political discussions. Your friendly debate will help him shape his arguments—and it would be good for you to acknowledge when he forces you to re-examine your beliefs. He also needs to understand that while being an academic whiz is great, it is not the only path to achievement. You’ve made a successful career despite your lack of a college degree. So instead of feeling like a dummy with your son, you should convey that you’re a confident, accomplished person. It’s bittersweet for any parent to watch their fledgling take off, but he’ll be more likely to want to spend time back at the nest if you can express your excitement for him, instead of your insecurity about yourself.


Dear Prudence,
My fiance and I are getting married this summer. We’re both in our 40s, and he has a 6-year-old daughter from a previous marriage. The custody arrangement is 50/50. However, his ex-wife is a flake and only wants to spend time with her daughter when it is convenient for her. If she wants to go out, she prefers not having her daughter, even if she’s scheduled to. She is not on drugs, nor is she a criminal. When we started planning our European honeymoon, my fiance insisted we bring his daughter with us. His reason was that he’ll miss her and is afraid her mother will not take good care of her. The daughter and I have a pretty good relationship, but I don’t feel comfortable with her going with us on our honeymoon. Am I unreasonable? Can I say “no” without coming across as an insensitive soon-to-be stepmom?

—Nice Stepmother

Dear Nice,
A trip to Europe with a 6-year-old is no honeymoon, and newlyweds are entitled to a private get-away. The issue here seems to be just how incompetent the mother is. If she truly can’t be relied upon to care for her daughter for the time you’ll be gone, then that means your fiance needs to reassess the custody arrangement. Perhaps he—with your agreement, obviously—should have primary custody. But it’s also not clear from your letter how bad a mother his ex actually is. If she is an inattentive parent who views her daughter as an inconvenience, that’s a serious issue. If the problem is that she sometimes makes changes to the child-care schedule on short notice, that’s annoying but not alarming. This situation needs serious thought and assessment, and it would be best to take that on after you return from the honeymoon. If your husband has any kind of decent relationship with his ex, he should tell her that he knows his extended trip will put pressure on her, and they need to formulate a child-care plan. Possibly grandparents or an aunt or uncle could take your stepdaughter for part of the time, which would be a treat for her and give her mother a break. Maybe your fiance can offer to pay for extra babysitting so his ex can have a social life while you’re away. At the least, in the gentlest way possible, he should arrange for another trusted adult to check in on his daughter and give him occasional reports so that he will be relaxed enough to concentrate on having a romantic trip with you.


Dear Prudie,
My family and my husband’s large extended family are all Facebook users. Currently, my husband and I are going through a very difficult time with one of our children. An extended family member posted the issue on Facebook, not in a mean-spirited manner but more as “keep the family in your thoughts.” Still, it frustrates me immensely that our personal business was posted and is being discussed by people I don’t even know. Should I be upset, and should I mention my displeasure with the culprit?

—Didn’t Know I Needed To Copyright My Life

Dear Didn’t,
Working out the etiquette of social networking is going to be a long process for society, full of hurt feelings and offense. With Facebook, a blabby relative now has the ability to spread confidential information with an efficiency not even achieved by a gossip in a Jane Austen novel. Of course this relative should have checked with you first, especially since the news is sensitive and concerns a child. You should contact this person and say you know no harm was meant, but you are distressed that your child’s troubles have been broadcast to a vast circle. Explain that you want to keep this a private matter and you’d appreciate from now on if your child was left off the news feed.


More Dear Prudence Columns

A Cornucopia of Crises: Prudie takes on Thanksgiving quandaries involving uninvited guests, the ghosts of holidays past, and exiled smokers.” Posted Nov. 18, 2010.

Bob & Carol & Ted & Malice: My parents’ swinger friends are trying to blackmail our family after Mom and Dad’s tragic deaths.” Posted Sept. 30, 2010.

No Debt of Gratitude: I borrowed cash from Dad to care for my dying mom. Now he’s demanding payback.” Posted Aug. 12, 2010.

Dirty Pretty Things: My girlfriend has worn the same undergarment for weeks. Isn’t that disgusting?” Posted Aug. 27, 2009.

More Dear Prudence Chat Transcripts

The Grinch Who Stole Thanksgiving: Prudie counsels readers on Turkey Day predicaments, such as flying solo for the holiday, hosting irritating in-laws, and attending multiple dinners. Posted Nov. 22, 2010.

Baby Mama Drama: Prudie counsels a sleuth who uncovered a baby-trap scheme—and other advice-seekers.” Posted Nov. 1, 2010.

The Family That Bathes Together: Prudie counsels a mother who wonders when the time is right to stop bathing with her little boy.” Posted Oct. 12, 2010.

Help! I’m Too Hot for My Age: Prudie counsels a woman whose youthful looks bring her nothing but problems—and other advice seekers.” Posted Feb. 8, 2010.

Like Prudie on the official Dear Prudence Facebook page and like  Slate on Facebook. Follow us on Twitter.