Emily Yoffe, aka Dear Prudence, is on Washingtonpost.com 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 firstname.lastname@example.org.)
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.