Dear Prudence

Help! My Stepfather Told Me He Had a Sex Dream About Me.

Read what Prudie had to say in Part 2 of this week’s live chat.

Photo collage of a man puckering his lips and a younger man raising his arms in disgust.
Photo illustration by Slate. Photos by sam thomas/iStock/Getty Images Plus and LittleBee80/iStock/Getty Images Plus.

Daniel Mallory Ortberg is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat.

Q. My stepfather told me he had a sex dream about me: I’m a 30-year-old trans man and am on vacation with my mom and stepdad (they married after I was already an adult). Yesterday morning, my stepdad described a sex dream he had about me in graphic detail. I have no idea what to do. I trusted him and felt safer with him than with my biological father. Not only do I feel disgusted and violated, but I feel like I just lost what I thought was a good relationship with a good man. What do I do? How do I tell my mom?

A: What a bizarre and inappropriate thing for him to do. I think the best way to broach it with your mother is not to try to worry about editing it so that it sounds less bizarre. Tell her that you’re totally baffled and hurt by his decision to go into great detail about his sex dream about you, and then figure out what you need to do next, whether that’s leave the vacation early, or go your separate ways as much as possible on this vacation until the return flight home. I assume you mostly just want distance from your stepfather, which strikes me as perfectly reasonable. I don’t think you should spend much time worrying about how your mother raises the issue with him. That’s their problem. Yours is just to say, “When you went into great detail about the sex dream you had about me, you destroyed the trust and ease that used to exist between us, so I’m going to go.”

Q. Saving up for an anniversary trip: My 20-year anniversary with my husband is six years away. Barring anything extreme, I foresee us hitting that milestone with the same happiness as when we hit 14 this month! I want to start to save up for a big trip to Monaco to see the Grand Prix, as I know this is something on his bucket list, and who wouldn’t want to spend a week in Monaco? The thing is, I would need to save up about $10,000 without him noticing in order to pay for the vacation package. I have a separate savings account from him, with an entirely different bank, but he is aware of the account as it is usually used for vacations or emergencies. Ten thousand dollars is a lot of money, and I’m not sure how I feel about squirreling away such a large amount. Is this something that’s OK to do since it’s a surprise? Is it wrong because it technically counts as hiding money from him?

A: Congratulations on 14 happy years—I hope you have many more. I certainly don’t think what you’re proposing is immoral, but I do wonder if the joy of the surprise would be outweighed by the stress and challenges of hiding a $10K savings account over the course of the next six years. What if you simply told your husband about your idea for a 20th anniversary trip and the two of you started to save together? If this were an amount of money you could manage to stash to the side over six months, I might have a different answer for you, but this seems like a pretty big chunk of your income. That said, you know your husband better than I do. If you think you could spare the money and that he’d love being surprised, you could always open a separate account so he doesn’t start to ask questions about your suddenly flush emergencies fund.

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Q. May I keep my TERF bangs? Hi! I’m an early-40s cis woman whose politics are progressive and 100 percent trans-inclusive. After trying out many, many haircuts on my hard-to-flatter face, I settled on baby bangs nearly two decades ago and haven’t looked back. (The rest of the haircut shifts in style and length, but my face needs those bangs.) I’ve been aware of the term “TERF bangs” for a while and appreciate the humor, but only recently a (cis) friend implied that actively sporting the style is an affront to trans folks, akin to the way neo-Nazis have adopted the Floppy Hitler. Can this possibly be true? Basically, you can pry my TERF bangs from my cold, dead forehead—unless you tell me they’re actively doing harm, in which case I guess it’s headbands for a while.

A: I’m not wild about the style myself, but I think your friend would have a difficult time convincing me that “short bangs” are as immediately recognizable and upsetting as a Hitler haircut-and-mustache combination. No, short bangs are not a conscious flag to “ask me about my transphobia.” For what it’s worth, I’ve only ever heard the association as a bit of a tongue-in-cheek joke; regardless of how seriously your friend takes that joke, you’re certainly not causing anyone any harm. Wear your bangs however you like, be kind to trans people, and don’t take any other advice from that friend of yours.

Q. Work crush may ruin my life: I am a fortysomething-year-old woman with two grown children and married to a genuinely lovely man. He is not the father of my children, but I am lucky that he is a wonderful stepfather (he has been in their lives for 15-plus years). We are financially OK, although both working full time to maintain that, and should be looking forward to some time together now that the children have become more independent.

However, I have fallen incredibly hard for a colleague at work. We’ve worked together for three years, and the spark was instant. A year ago something almost happened between us, but I reversed out of it before the damage was done, something that admittedly I sometimes regret. We have a lot in common, have lengthy discussions about everything and anything, and message each other outside of work (although we’ve never met up). This colleague now has a partner, but doesn’t hold back in how “annoying” she is (not just to me, but to everyone in the office). He has mentioned that he might end up marrying her as it’s “what she wants,” but eyebrows were raised by everyone in the office as he doesn’t actually seem that fond of her. When I heard that he might marry her, I felt like I’d been punched in the gut.

I seem to be obsessed, and I need to get him out of my head. My husband deserves better than this. He’s a kind and caring man who tells me he loves me every day, sends me thoughtful messages at work, buys me flowers when he knows I’ve had a tough day. On paper he is perfect. And yet I am thinking about another man day and night. It’s selfishness beyond belief, I’m not proud of myself, and if my husband even suspected my thoughts, he would be destroyed and my marriage could well be over. Finding a new job is the obvious option, but not seeing this guy ever again is something I cannot handle at the moment. I have everything but risk losing it all. What’s wrong with me? I thought I was too old for this madness.

A: Leaving aside for the moment what’s “wrong” with you, I think one thing that’s important for you to remind yourself of is this: The man you desire speaks cruelly and dismissively of the woman he’s in a relationship with, and that speaks volumes about his integrity, his honesty, his trustworthiness, and the way he views women. More than that, he’s apparently willing to marry someone he feels contempt for merely in order to keep the peace, instead of making difficult choices that prioritize his own happiness. More than even that, he’s also decided to vent his frustrations by tearing her down with his colleagues behind her back, putting everyone he works with in the deeply uncomfortable situation of having to know just how little he respects her. That combination of weakness and cruelty is absolutely soul-crushing, and I have no doubt that if you were ever to get further involved with him, he would be weak and cruel in much the same way to you. When he criticizes her to you, it’s not a sign that he’s secretly trapped in an unhappy relationship and would be better off with you; it’s a sign that he treats his girlfriends badly and likes to leave open as many exit strategies as possible, in case he decides to cheat on them.

As for what may be wrong with you, I think the best place to start exploring some of these thoughts/fears/impulses/desires is in therapy, since you’re not yet ready to share any of them with your own partner. There’s clearly a part of you that’s either bored or feels unworthy of a partner who respects and affirms you, and at least some of the time you want, or believe you deserve, a partner who’s inconsistent, hypocritical, selfish, dismissive, hard to reach, and emotionally unavailable. You don’t want to cheat on your partner, but you’re also not willing to foreclose the possibility that someday this other man might want you, which is why you stopped short of going to bed with him but still talk to him about “everything and anything” and keep texting him after-hours. I don’t think this strategy is bringing you a lot of joy and comfort, and I think that time would be better spent with a therapist uncovering and challenging some of your ideas about what you deserve in a relationship. It might also make it easier to set some new boundaries with your co-worker; you may find you no longer want to text him once you’ve gone home for the day after you’re able to acknowledge his smallness, his meanness, his inability to provide you with anything other than self-recrimination, self-loathing, insecurities, doubt, and uncertainty.

Q. I’m just not that kind of lawyer: I’m a lawyer but in a very specialized area, an area I’ve been in for 16 years. I get the typical questions from family and friends that all lawyers do, and if I can offer free advice, I do, even if it requires some research on my part. But generally, if it’s serious, I help them find a good lawyer in that area. My good friend has a very serious ongoing claim against her employer. Early on I realized it was outside of my wheelhouse, and I helped her hire a really good lawyer I know personally. I’m there to support her as a friend, but that does not stop the legal questions on weekends, late at night, and daily. She’s very anxious—with good reason—and I suspect the lawyer does not answer as quickly as I do. At this point I’ve just provided supportive commentary with direction to speak to her lawyer. But she keeps asking. It’s starting to overwhelm me. I’ve tried to explain that this is way out of my area and I don’t feel comfortable advising her! But she’s started to get angry with me for not helping her. This would be like asking an orthopedic surgeon to do breast implants. But she does not get it. How can I be her friend but not her lawyer?

A: Tell her exactly what you’ve told me, this time not waiting for her to ask another question that you have to dodge—that you understand her anxiety, but you are not the lawyer on this case and are not able to give her good or specific advice, that her questions are getting overwhelming and way out of your depth, and that you want her to think of you only as a supportive friend, not as a backup lawyer. If you want to soft-pedal this, you can say, “This isn’t because I don’t want to help you—it’s because I can’t give you good, specific advice without being part of your legal team and staying up-to-the-minute on the case. Even if I were to try to give you answers to your questions, they wouldn’t be accurate, and you might end up worse off than you were before. I promise I’m not holding anything back from you. I really just can’t answer, and it will be better for both of us if you stop.”

Any other lawyers who want to chime in here, please let us know what’s worked for you, if anything does.

Q. Fast and furious: A few months ago I was in a really bad car wreck which I was not at fault for. The other driver was speeding. Although I am fine now, every single person who saw the accident or saw my car after the accident was amazed that I am still alive. I was extremely lucky. The problem lies with my younger sister (and a few of her friends). My sister is a terrible driver, although she mostly relies on rides from her friends to get around. I actually felt relieved by this, because then I knew someone more responsible than she is would be at the wheel. Yesterday, one of her good friends gave us a ride. I was sitting in the back seat and noticed her friend was animatedly chatting, singing along to the radio, getting distracted, and even looking at her phone while she was going 90 to 110 miles per hour on the interstate. This part of the interstate winds and bends and is very crowded, and there are a lot of exits and merges. Most people go 65–70 max on that road. I didn’t have too much driving anxiety after the accident (surprisingly), but I was completely paralyzed for the entire car ride. I didn’t say anything because my sister often makes remarks that I “worry too much and it’s embarrassing” or that I’m “too uncool” to hang out with her friends. We are generally pretty close and we’re both adults, so it’s not like I can tattle to my parents. She’s been talking a lot about how it was so nice of her friend to give us a ride, and I haven’t said anything besides nod my head. Now that I know how her friends drive, I’m even more terrified of her dying in an accident than I am myself. How do I explain this to her without her brushing me off? She claimed I was overdramatic after I spent weeks in the hospital following my wreck.

A: Even if you hadn’t recently been in a serious car accident, you’d be well within your rights not to accept a ride again from someone who drives 40 miles over the speed limit while looking at their phone. The good news is that you get to hold that boundary even if your sister thinks you’re being “dramatic” or a wet blanket. She can’t brush you off if you refuse to get in the car when she or her friend is driving and you make your own separate arrangements for a ride from a safe driver. She might say something dismissive, which is irritating, but she can’t force you in the car. You, for your part, can say, “You don’t have to agree with me, but speeding/texting while driving is demonstrably unsafe, and I’m not going to ride with you.”

I think the reason she’s been gushing over and over again about her friend giving you a ride (which is a pretty commonplace favor, and not one that people normally spend days expressing gratitude for) is because on some level she knows she and her friend are in the wrong but doesn’t want to feel guilty about it or commit to changing her behavior. Her goal is to get you to admit that speeding and texting aren’t really that bad, and that your car accident was simply a freak accident that could never happen again, so that she can go back to not examining her choices as a driver. You do not have to help her reach that goal! I’m truly sorry that she tries to make you feel like you’re not cool enough to be around her friends—that’s pretty unkind—but I think the best response to that is not trying harder to conform to her expectations, but sticking to your guns and responding with a neutral “OK then, I’m still going to get my own ride.” If her idea of being dramatic is spending weeks in the hospital receiving medical treatment, then her definition of dramatic is pretty off-base, and you should not accept her terms of what’s cool or uncool, what’s laid-back or dramatic, what’s safe or unsafe, what’s reasonable and what isn’t.

Q. Same-sex wedding questions: I’m getting married to my wonderful fiancée in a few months. Both our families are attending the wedding. For very good reasons having to do with religion and her relationship to her parents, she doesn’t want them to walk her down the aisle; she’s set on going solo. I respect and understand this, but I can’t figure out what I want to do. I’m really close with my parents, and they’ve been nothing but loving and supportive of me and our relationship. It would mean so much to me, and them, to walk down the aisle with them, but the inequality would highlight the differences in our families in a super public way. I’ve wracked my brain trying to think of graceful compromises and can’t come up with anything. If it affects the issue, we’re paying for the wedding, not our families.

A: I’m not sure that it does highlight the differences in your families! Or rather, I’m not sure the way in which it highlights your differences would be as obvious as you fear. One of the many advantages of a gay wedding is that everyone attending is pretty prepared for the brides to pick and choose what traditions they want and which ones they don’t, so it may very well just look to the attendees like one of you wanted to have a slightly more traditional “bride” moment in being walked down the aisle, and the other didn’t. Maybe there’s some other way your fiancée wants to acknowledge her parents, even briefly, during the ceremony (by doing a reading, handing over the rings, something else) so the two of you don’t feel like the imbalance is so obvious. But overall my advice would be not to worry that you two aren’t making mirror-image choices during the ceremony. Nobody is expecting you two to do the exact same things just because you’re both brides, and if you want to walk down the aisle with your parents and she doesn’t, I think everyone will completely understand.

Q. Re: Saving up for an anniversary trip: When I was in this position, I asked my husband if he would mind if I put money away for a surprise. His reply was that given our current financial state, he would resent missing out on the odd restaurant meal whilst knowing there was a pot of money available.

A: That’s the key here, I think. It’s a big enough chunk of money that your partner might reasonably want to be consulted on how to spend it as part of a team. If you put in all that work and energy into saving $10,000 only to find out six years from now that he would rather have spent some of it on something else, then you’d have lost the whole point of the enterprise, which was to experience something delightful together and to give him a pleasant surprise. I do think you’ll be happier asking him how he would feel about the occasional big-ticket surprise, if he’d prefer to be consulted, etc. (without going into exact details about your Monaco plan), and then adjust your plans from there. If he says, “Yes, I adore surprises, and as long as we’re not struggling financially, I’m happy to know you’re saving up for something mysterious in the future,” great! If he says, “That would feel stressful, and I wouldn’t really enjoy it,” then you know more about how to surprise him in ways he would enjoy—like maybe a nice meal out for a few hundred dollars or even a weekend away, while continuing to save up for big-ticket, long-term splurges as a team.

Q. Re: May I keep my TERF bangs? I say treat this hairstyle like the “Can I speak to your manager?” haircut and know that it’s a stereotype used to make jokes but not actually causing any harm.

A: Right, those both fall into the same category, I think. It’s a slightly tired joke at this point, but it is a stereotype of association, not causation.

Daniel Mallory Ortberg: Thanks, everyone! See you next week.

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

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From How to Do It

Q. A guy dumped me because I can’t orgasm. Should I start faking it? I’m a woman in my late 20s and I’ve been casually dating for a few years, not really looking for anything serious but open if I find the right person. When I’m alone, I don’t have much of an issue climaxing with my vibrator, but my orgasms have always been a bit underwhelming. However, no matter what I or the guy does, even if I use the vibrator with him there, I can’t seem to get off with someone else around me. Especially when I was a bit younger, this was something that I really struggled with, but I’ve gotten to the point where I just accept that it’s a part of who I am. It doesn’t stop me from really enjoying sex and feeling close with a partner, even if there’s no fireworks conclusion.

My issue is the guys I’m sleeping with. Before we have sex, I let them know that it’s not going to happen for me, so they aren’t expecting me to. The reactions I get vary widely. Some guys seem to think it’s an excuse to not try at all, and others seem to think that theirs is the magical penis that will solve all my problems and get incredibly disappointed when they realize that it won’t. I’ve had a guy burst into tears because he “couldn’t please me” and another who told me that I wasn’t meant to be with anyone because I couldn’t orgasm. Most hurtfully, I had a boyfriend break up with me because “How can I love you if you can’t orgasm?” I don’t know how to make the men in my life just take me at face value when I tell them that I really am enjoying myself and not to worry about it. Should I stop telling them? Fake it? What I’m doing doesn’t seem to be working.