Dear Prudence

Help! I’ve Made It My Mission to Have Sex With My Older Co-Worker.

I told him the chase was back on.

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Photo illustration by Slate. Photo by Getty Images Plus.

Our advice columnists have heard it all over the years. Each Sunday, we dive into the Dear Prudie archives and share a selection of classic letters with our readers. Join Slate Plus for even more advice columns—your first month is only $1.

Dear Prudence,

I work for a small business and am very close with my co-workers. We often spend time together outside of work. I’ve spent the last few months subtly flirting with a co-worker who is 20 years my senior, but I’ve never attempted anything further as he is in the middle of a divorce, although I am very close with his children. About a month ago, I was at his house while his family was away, and we established that we are attracted to one another. We decided to proceed with a “friends with benefits” situation since our relationship is complicated. We hooked up but did not have sex. At the end of that week, he told me that he preferred the sexual tension and “the thrill of the chase” to our new arrangement, although he did not want to ruin our friendship. I was not interested in that as I felt rejected.

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After a few days, I realized that I may have appeared too clingy and annoying—especially since a man in his 40s probably does not want his hookup texting him every day. I am never the clingy one, and it irritates me to think that I was. So I told him the following Monday that the chase was back on. Our flirtatious behavior has since become much more intense, while remaining discreet. It has now become almost a game in my head to have sex with him. I am not sure why. Should I make a move or bring this up with him? I would like to establish that relationship with him, but I am unsure if I ruined it by being too overbearing. Where do I go from here?

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Oh, yikes. This letter started unraveling about two sentences in and I’m not quite sure where to start. Let’s start with the fact that your co-worker—a still-married man in his 40s—is apparently in the habit of inviting his twentysomething female colleagues over to his house while his children are away. Depending on your age, this may be one of your first full-time jobs, and it’s worth repeating that this is not normal office behavior, not even for an office that’s especially “close.” I don’t think you were annoying or clingy by texting this guy on a daily basis for a week. I think becoming friends-with-benefits with him was ill-advised and potentially bad for your career, but it’s not inappropriate to regularly text someone you’re hooking up with. I think he’s a creep and a bad employee (he can’t be getting much work done if he’s got this much time to play Dangerous Liaisons–level mind games) who took advantage of your youth and inexperience and is jerking you around.

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It would be a lousy move for him to pull even if he were a guy your age you met at a bar and started sleeping with casually; the fact that he did this while you two were supposed to be working together speaks volumes about his character and professional standards (or lack thereof). To answer your question, then: The best place for you to go from here is out of this weird, boundary-less, incestuous little office and into a sane workplace with a robust HR department. —Danny M. Lavery

From: “Help! I Want to Keep Hooking Up With My Older, Married Co-Worker.” (Aug. 3, 2017)

Dear Prudence,

I have been in a good marriage for more than a decade, and we have had what I consider to be a normal, loving sexual relationship. With one major exception—my wife has never achieved orgasm with me. She has always told me it is not a big deal to her, although we have certainly tried and it is something we have discussed repeatedly. She is able to achieve orgasm by herself, but never with me, and she’s said never with any other man. A few nights ago, she accidentally let slip that she did achieve orgasm with her ex-husband. Upon further discussion it turns out it happened many times and very easily. I’m devastated. Why did she never tell me before, given the number and intensity of our discussions on the issue? Am I such a wretched lover that I am hopeless? She feels that since her ex cheated on her, her defensive walls went up and she won’t let herself be vulnerable or trusting enough. I am in quite a tailspin, and she recognizes how deeply I am hurt by this admission and she feels terrible about it. But it’s not something that’s going to be easy to push out of either of our minds when we next try. Help!

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So your wife associates orgasmic sex with an ex-husband who ended up cheating on her. In her mind, having an orgasm with her devoted, faithful husband of more than a decade is a psychological barrier she doesn’t want to cross, because it will remind her of what a good lover husband No. 1 was. This is taking Pavlovian conditioning to new and self-punishing levels. I guess you’re lucky your wife agrees to intercourse at all, since that was something she did with her ex. Her reasoning could be extended even more: “Jerry and I used to eat out a lot, but I found credit card receipts showing he ate out with Elaine—so I can never eat in a restaurant with you.” If you’d said that no partner of yours had ever reached orgasm, I might have suggested you lacked peak performance skills. But you seem to have worked assiduously to get her off. Now comes the revelation that she can climax at the drop of the pants—just not with you. I agree that your next time in the sack is going to be rather tense. So you need to talk more with your wife about this before getting into bed. Don’t be sorrowful or defensive—instead act as if this has the potential to be wonderful news. Ask your wife if there’s some magic trick that her ex did that you would be more than happy to try to incorporate—maybe you will discover some terra incognito of her erotic life. But if it truly is a psychological barrier, you need to make clear it’s diminishing the pleasure both of you get from your intimacy, and that all these years later you hope she can let go of what was a specious connection to begin with. Even if the most she can do at this point is masturbate in front of you that could be a breakthrough that leads to more mutual satisfaction. —Emily Yoffe

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From: “Help! It Turns Out My Wife Can Orgasm During Sex—Just Not With Me.” (July 30 , 2015)

Dear Prudence,

I took an at-home DNA test three years ago and loved it—I learned more about my family history and some potential health issues. I eagerly suggested to my husband that he take it as well. He just took it and figured out he has two half-sisters he never knew about. After two days of denying it, his parents finally confessed that he was born via an egg donor and his mother isn’t his biological mother. He’s absolutely distraught.

I feel the blame is with his parents for hiding this secret for 30-plus years. He feels guilty for taking the test and responsible for the emotional meltdown it’s caused in his family. How can I support him through this? Am I right to be angry at his parents for hiding such a salient fact for so many years? Are my feelings of guilt at having recommended this test in the first place valid? Please help.

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This is a complicated situation, and part of why it’s important to ask, Am I prepared to learn something potentially devastating? before taking any sort of genetics test, rather than embarking on it as a lark. I imagine that your husband’s parents may have felt a degree of shame and sadness 30 years ago and didn’t know how to talk about egg donation with their children. That doesn’t mean your husband is wrong to feel distraught, but I don’t think they kept it to themselves purely out of a desire to be withholding.

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You’re all still in the immediate aftermath of a pretty serious revelation. With time and conversation, this may go from The huge family secret that ruined everything to The complicated circumstances of how this family came to be. My guess is that at least some of the anger toward your husband’s parents is an attempt to manage the feelings of guilt you have about your own role in this discovery. You need to work through both—one isn’t going to cancel out the other. Talk with your husband, encourage him to seek therapy, support whatever decisions he makes regarding whether to try to contact his half-siblings, and remind yourself that you can’t fix this situation, only walk through it with him. —D.L.

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From: “Help! My Husband Just Learned His Family’s Biggest Secret Through a DNA Test.” (Sept. 24, 2018)

Dear Prudence,

One of my close friends just announced his engagement to a woman he’s been dating for a few years. We’re happy for him, but many of us can’t shake the feeling that he’s making a mistake. In essence, the woman makes fun of him a lot in front of his friends, and not in a loving way. Our friend often looks uncomfortable when this is happening but says afterward he’s very happy with the relationship. She talked for several minutes about how he always gets her the wrong presents (including the engagement ring), makes fun of his clothes, etc. The couple lives in Chicago while the rest of us are on the Eastern Seaboard, so none of us has spent a tremendous amount of time with them. (They stayed with me for two nights last week, the first time I had met her.) My question is, should someone say something to our friend? He says he’s really happy, and nobody wants to ruin that for him, but some of us worry that this marriage is doomed from the start. On the other hand, nobody wants to be the friend forever marked as the one who tried to kill off the relationship. What do you advise?

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Think of what happens if you don’t say something. Because he lives in another city, every time you see him, it will probably be with her. Then after spending the evening listening to her put-downs and insults, you will eventually feel, “I love him, but I can’t stand her, and I’m not sure I can spend time with them as a couple.” I’m a big advocate of teasing—but it has to be mutual, fun, and good natured. This sounds one-sided and nasty. It’s odd when someone you like picks someone for a partner who seems so unsuitable, so unlikable. But I think one of you has to speak up—gently—and express your concerns. You can say you know he is very happy with her, but after the last get-together, you were left feeling very uncomfortable with the way she treated him. Say you know you are stepping into dangerous territory by saying this, but you care for him too much not to point it out. Maybe he’ll reassure you he finds her remarks hilarious. Maybe you’ll have touched such a sensitive nerve, and he cuts you off. But I think your friendship is worth the risk. —E.Y.

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From: “Engaged To Be Harried” (Oct. 25, 2010)

More From 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. 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?

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