Dear Prudence

Pushing the Wrong Buttons

In a live chat, Prudie counsels a widow whose new love has no clue how to please a woman in bed.

Emily Yoffe.
Emily Yoffe

Photo by Teresa Castracane.

Emily Yoffe, aka Dear Prudence, is on 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

Q. Mature Relationships: I am a widow in her early 60s in a very serious, hopefully permanent, relationship with a kind, caring, successful mid-60s widower who would be ideal except that he is clueless about the female anatomy and how to please it. That his late wife never went down on him in 30-plus years of marriage suggests there was a lack of communication that explains his problem. Although he is unselfish, enthusiastic, and believes he drives me wild, he never finds the target. I am very sexual, orgasmic, and quite experienced, so this lack of knowledge frustrates. To complicate matters, after my husband died, I met two lovers extraordinaire, contemporaries who rocked my world, but have few other redeeming qualities. How do I tell a sincere man that he needs remedial sex school without offending or deflating him? Also, since in my 60s I know I will never find the perfect man, is an occasional tryst with an expert solely for therapeutic purposes justifiable?

A: There is a serious disconnection in your description of your lovemaking (or perhaps we should call it stumblebumming) with your beau. If even after 30-plus years of marriage this guy’s unacquaintance with the female anatomy means he can’t “find the target,” then you are seriously misleading him if he thinks this shooting and missing is leading to your ecstasy. Leaving the impression that someone is a great lover when in reality he is utterly inept makes suggesting remedial action all the more difficult. But if you intend to make him your intended you must address these deficits. It sounds as if you have enlightened him about the interesting things that happen when genital meets mouth, so at the very least you can be assured of his attentiveness. Yes, you have to approach this delicately. But address it you must or else all his other wonderful qualities will seem like a tease because you’ll primarily think of him as a dud in the sack.

Since you’ve established your sexual bona fides, tell him you want to keep adding to your repertoire. Find some instructional videos that are erotic but not hard core (you don’t want to have defibrillate the guy) and watch them together. Note while you watch the things that turn you on. Then afterward, don’t be afraid to guide his hand, and other parts, as you show him what you like. Clearly what his wife liked was three minutes in the dark, so anything beyond that is a mind-blower for him. If things never get better, you have some decisions to make. But I’m not going to be the one to give you carte blanche to cheat if you’ve voluntarily signed up to be under sexual duress.

Dear Prudence: No-So-Secret Life

Q. Gay Table at Wedding?: I am getting married in the fall and we are inviting a fair number of gay couples and single people. Enough to fill a few tables. Some of these guests know each other and some of them don’t. Would it be inappropriate to have a few gay tables? I don’t want to create small gay ghetto but genuinely think that they would like to meet each other and will get along really well. Should I distribute the gay guests throughout the wedding just to avoid having gay tables?

A: If you have friends of any sexual orientation, religious persuasion, etc. who you think would like getting to know each other, make sure that while you are circulating you introduce these people during the festivities. But don’t play, “What do we all have in common?” with your seating chart.

Q. Mom’s Private Investigator: I love my mom and her parents, but I’ll be the first person to tell you they can be elitist. My sister, who lives across the country, didn’t tell them about her boyfriend for almost a year because he is a teacher, and she knew they’d disapprove of his low-paying occupation. My sister and her boyfriend have been discussing marriage. My mom surmised as much, and she hired a private investigator to follow my sister’s boyfriend. The P.I. didn’t find anything, but my mom continues to employ him. I want to tell my sister about the P.I., but I know telling her will cause a lot of family drama. My mom will also know I told my sister and will be angry with me. I think my mom’s wrong, but I’m young enough that I have to live with her for another year. It’d be nice if we didn’t argue all of the time. Should I tell my sister or not?

A: Sorry to tell you that your mother and grandparents sound rather despicable. Disapproving of the teaching profession is bad enough, but hiring a private detective without cause to dig up dirt on her daughter’s boyfriend makes your mother the dirt bag. She was hoping she’d get evidence he was a pedophile, instead she learned he grades on a curve. It’s probably not a coincidence that as soon as she could move away, your sister choose the opposite coast. That she has hidden her marital intentions from your mother also indicates your sister knows what a head case Mom is. I think eventually your sister should know about the investigator, but because you would be the clear source, I’m going to tell you to keep it to yourself for the next year. This is simply to reduce the “living hell” factor for you. Soon you will make your own escape. I understand you love your relatives, flaws and all, but life will likely be much better once you are able to put some distance between yourself and their judgments.

Q. Re: Mature relationships: I’m in my 30s, but have the same problem—a guy who lacks a basic understanding of how to please a woman. I agree that this needs to be approached delicately (regardless of age), but what’s your advice on how to actually bring it up without totally deflating a guy’s ego? I’ve tried in the past, but no matter my level of kindness and understanding, it inevitably leads to insecurity issues that then snowball and manifest in other parts of the relationship. The male ego is so fragile, especially in the bedroom!

A: If it’s that fragile, I think you need to look for a stronger vessel. No one wants to be told, “Wow, you are the worst sex partner, ever!” But most people also know that there is always more to learn sexually and that what pleased one partner might not please another. It sounds as if you have tried addressing this and have been thoroughly rebuffed. This problem with this guy likely isn’t fixable so either you grit your teeth or move on.

Q. Grasshopper and the Ant: I live with my husband and son in a different state than my parents. We are scheduled to go back for a visit next month and I am very anxious about this trip. Both of my parents, who are divorced, have recently asked me to either a) loan them large sums of cash or b) to invest in their get-rich-quick scheme (there is a reason I live out of state). Like good worker ants, my husband and I have fairly successful careers and have always lived within our means and not extravagantly. I am pretty annoyed by these requests and logically do not feel bad about denying them, although honestly I do feel somewhat guilty. The grandparents have not seen their grandson in over a year (they do not come visit us) and I would like to have the visit go as smoothly as possible and I am sure I will be subject to guilt trips and/or the silence treatment. Any advice for dealing with aging con-artist grasshoppers?

A: This is a refreshing change from the usual letter I get on this theme. In those cases the worker ants have bailed out the grasshopper parents so many times that their own financial statement looks like it’s been beset by locusts. You just keep doing what you’re doing, except for the guilt. Your parents have made their own mistakes, and given that they want you to finance more get-rich-quick schemes they haven’t even profited from learning from their errors. Be prepared to say, “I’m sorry things are tough. Unfortunately, we just don’t have a cent of disposable income.” Because any income that you give them might as well go down the disposal. If doing that means the visit turns stony and silent, cut the day short and say you’re sorry they don’t seem to be in the mood for company. Comfort yourself that you haven’t repeated this pattern and that your son will never feel this way about you.

Q. Rage-Filled Nephews: My sister-in-law wants to move to South America so she can be closer to her boyfriend. She does not want to take her two sons, 15-year-old Chris and 6-year-old Matt, with her. She assumed my husband and I would take them in, as her parents are too infirm to be their caregivers. While my husband and I could afford to care for our nephews, we’re hesitant to do so. Chris and Matt have serious anger management issues. Matt will throw tantrums, bite people, and lash out at pets when he’s angry. Chris, who is much bigger, will punch holes in walls, scream at the top of his lungs, and break furniture. My sister-in-law has always made excuses for their angry outbursts, but because we have young children, my husband and I don’t feel comfortable inviting Chris and Matt to live with us. My sister-in-law seems determined to move, though, and without us we’re not sure where Chris and Matt will live. My sister-in-law tries to guilt us whenever we explain to her why we’re not comfortable having her sons live with us; we’re not sure what to do that’s in the best interests of the children involves.

A: What a tragic situation all around. But you cannot be guilt-tripped into taking in two violent angry boys. Since their mother is determined to abandon them, and apparently there is no father, you need to tell her you are calling in the authorities to take over the handling of her sons. I hope the state steps in and gets these two the therapeutic help they both desperately need.

Q. Language—Using Word Retard: I have a short-term roommate who has a penchant for using the word retard—all the time. If you watch TV with him, it’s always “who’s that retard?” or “why is she with that retard?” None of the people he’s referencing, of course, have actual mental disabilities; he’s just calling them stupid. I find it very cringe-inducing, and I’m sure have winced before when he has said it. I know a lot of people have used/still use it, but it seems to be rightly fading away. On the one hand, I find it offensive and keep itching to say something. It seems like he should at least be aware that some people find it inappropriate. On the other hand, we won’t be roommates for much longer, and I’m not sure how appropriate it would be to correct the language of someone I’ve only known for a couple of months. Is it worth it?

A: You shouldn’t have to cringe when relaxing in your own home, so speak up. Phrase it in a way that give him the benefit of the doubt: “Charley, would you mind not using that word? I know it used to be in common usage, but it’s now considered offensive and it makes me uncomfortable. Thanks so much.” Let’s hope he takes this graciously, but do be prepared to be told you yourself are lacking in the intellectual capability department. If you get the latter response, try not to react, and just happily mark the days on the calendar until he’s gone.

Q. Lying Supervisor: At my job there is a person above me in rank, but not my immediate supervisor. He insists on being called a specific title, and everyone does it, from entry-level people all the way up to the vice president of the company. I found out a few weeks ago that he never earned this title properly (to put it into context, it would be as if he had studied to be a paralegal but expected everyone to call him “Judge Smith”). After I found this out I immediately started calling him Mister Smith, which basically enraged him and I got lectured by him on what he “deserved” to be called. I don’t have a lot of contact with him, and the time he asked me to do something for him (when he got so mad) I said “Of course Mister Smith” with a big smile and absolutely no sarcasm or malice in my tone. I have a lot of friends who have studied law, medicine, and even culinary arts, so I know what kind of time and effort it takes to have a title or a set of letters accompanying your name. I don’t feel I should humor this guy just so he can have an ego trip. I don’t want to start trouble in my company by whistleblowing what I know about him, but I also don’t want to get IN trouble or lose my job by calling him this different name. Should I just go along with everyone else even though I know it is wrong? Or should I keep calling him Mister?

A: Just keep a straight face when you call him “The Right Honorable.” He sounds pathetic, but at any workplace you will have bigger issues to use your chits on than making an issue out of giving a verbal ego stroke to a silly co-worker.

Q. Re: Gay table at wedding?: As one part of a gay couple, no no no no no. We will notice it really quickly, it will be very awkward, and you’ll be discussed for years as the woman who created a gay ghetto at your wedding.

A: Exactly!

Emily Yoffe: Thanks, everyone. Talk to you next week.

If you missed Part 1 of this week’s chat, click here to read it.

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