Dear Prudence

Help! I Had a Sex Dream About My Sister’s Fiancé. Is It Weird if I Pursue His Twin?

Read what Prudie had to say in Part 1 of this week’s live chat.

Photo collage of fraternal male twins and a woman between them, lovingly daydreaming about one of them.
Photo illustration by Slate. Photos by OSTILL/iStock/Getty Images Plus and esthAlto/Matthieu Spohn/PhotoAlto Agency RF Collections via Getty Images Plus.

Dear Prudence is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat.

Danny Lavery: Good afternoon, everyone. Let’s chat!

Q. Sister’s boyfriend’s twin: My sister is engaged to the perfect guy: handsome, funny, devoted, and even volunteers! I love how happy she is, and I am more than a little envious. And he has a twin brother (fraternal but pretty close). We met a few times at my sister’s and did the friendly/flirty thing. He is single and just moved here. He seemed interested in me. Would I be the worst sister in the world if I pursued this? The weirdest? If I am going to vomit out my soul here, I had a few confusing sex dreams about my soon-to-be brother-in-law way back when my sister just started dating him. (He is very good-looking.) I would die before ruining her wedding, but I don’t know what is worse, telling her and potentially stressing her out or just keeping it on the down low. I don’t know if the guy would even be interested, but you never strike a home run if you refuse to get up to the plate. What should I do?

A: On the one hand, you are contemplating something pretty straightforward. You’re a single woman interested in asking out a single guy who seems interested in you! He’s not your sister’s ex, they don’t have a painful history together, he’s never hurt her or treated her badly. You found a guy who looks a lot like him to be really attractive when you first met him; that guy happened to be your sister’s fiancé, but you never flirted with or behaved inappropriately with said fiancé. None of this is cause for concern, nor does it rise to the level of “wedding-ruining.” I agree that it would be thoughtful and considerate to give your sister a heads-up either before you ask him out or after he’s said yes to a date, not because you want to give her veto power over your dating life but because she knows both of you pretty well. If I were in your position, I’d only tell her after he’s said yes. I assume you’re already committed to attending her wedding and treating him politely if he turns you down; that’s pretty much all you owe your sister in this case. Good luck!

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Q. She’s still doing the fam thing with the ex: My girlfriend and I have been together/exclusive for more than two years. We’re not kids, and there is a significant age difference—I’m 60, she’s 40. She has a 12-year-old child and, by her own admission, is not mother of the year. But she genuinely loves her son and wants to do what’s best for him. What’s best, in her mind, however, means perpetuating a myth of a semi-intact family with her, her husband, the child, and the grandparents. They all get together fairly frequently—events to which I am decidedly not invited. I’m ready to end the relationship over this, but her response is “Why do you care? He [her husband] is still the father of my child, and he’s going to be part of my life.” I say, “Well, perhaps, but if we are a couple, then he has to step aside.” Am I being selfish? I actually enjoy our time apart when she does the fam thing, if I’m being completely honest. I have zero interest in being a stepdad. I have four grown children of my own.

A: Yes, you’re being selfish and, equally important, quite silly! Spending time with your child and their other parent is not “perpetuating a myth”—it’s parenting. Neither is getting together with your kid’s grandparents. If she and her ex were pretending to still be married and she tried to pass you off as “just a friend,” that might fall under the category of mythmaking, but what you’re describing here just sounds like an amicable co-parenting setup. They’re raising a child together, and you have no grounds to ask her to stop just because you want to hang out more; the idea that her child’s father should “step aside” so her boyfriend can take her to the movies more often is absurd. You say you’re decidedly not invited to these family get-togethers, but you also say you have “zero” interest in being a stepparent. You should break up with this woman and date someone who doesn’t have children!

Q. Parsing my commitment phobia alongside my transition: I just ended a five-year, mostly long-distance relationship after a series of long, drawn-out, horribly difficult and sad conversations, a major theme of which was my own uncertainty and insecurity about the prospect of moving in together when I finish grad school in May. I didn’t realize that so much of my partner’s hurt and sadness came from my inability to commit to her in this way, and I am devastated that I couldn’t overcome this uncertainty and be that person for her. I’ve been out as nonbinary and using gender-neutral pronouns for four years, and after an initial consultation, I made an appointment months ago to get my first hormone replacement therapy prescription this week. I am so excited to finally have the experience and gain some morsel of certainty on whether hormones are right for me.

My impossible question is: Can I expect my transition to ease my near-constant insecurity and indecision in other areas of my life? So much of it has always felt tied to my gender and feeling like I can’t trust my own thoughts and feelings because they are so subject to change. I sometimes feel like commitment phobia and dysphoria are part of the same package. I really like the idea that gaining some confidence in my relationship to my gender would make me better equipped to not hurt people I love with my indecision and insecurities, but I also know I can’t necessarily count on that. I feel simultaneously excited, nervous, overwhelmed, and hopeless. I need a pep talk or some tough love or both. Help!

A: Transition can help with a lot of things, but you’d be unwise to assume that simply starting HRT will immediately and uncomplicatedly put you in touch with your own mind and enable you to clearly, consistently communicate your desires to other people. That sort of change only comes from practice. I’d say a better approach is to consider this hormonal-test-drive period an opportunity for some (written) soul-searching. There’s a reason people often record their impressions of the first few weeks or months on HRT! It’s a cliché for a pretty good reason. As much as you’re able, write down what you’re noticing not just about the physical effects but your own reactions, hopes, desires, fears, etc. If it helps to write out a sort of “relationship ideal,” try that. By which I don’t mean “I want a __friend who’s this tall and has that job and treats me X way” but how you’d like to feel and behave in future romantic relationships, how you might be honest and forthright even in the absence of certainty. What would it look like to acknowledge your own uncertainty and to treat it with respect, while also offering potential partners a lot of room to make their own decisions about how much uncertainty they’re comfortable dealing with? I do hope that trying HRT is a useful, clarifying exercise for you, but I don’t want you to write off past uncertainty as a side effect of dysphoria that you can trust will be permanently exorcised now that you’re on hormones. The hormones may give you space to do the work more readily and with greater confidence, but the work still remains to be done.

Q. Should I give my niece a wedding present? When each of my four nieces graduated from college, I took them on a long international trip. While on the trip with “Carrie,” she told me that she was going to be maid of honor for her roommate in a few years. While traveling, Carrie saw a present that she thought would be perfect. It cost $200, and she didn’t have it. She asked if I would loan it to her. I did, and she bought the gift. When we got home, she thanked me for the trip, and we parted. She lives in another state, so I see her at most once a year. It is now 15 years later, and she’s getting married. It’s a destination, and she’s decided to keep it small, just the couple’s immediate family and a few friends. I am not invited, which is fine because it’s not a destination I would enjoy. I don’t know what, if any, gift I should send. It’s been 15 years, and she has never referred to either the trip or the money I loaned her.

I feel somewhat petty, but it really bugs me. If I just send a card saying “Congratulations! Consider that $200 repaid as my gift to you,” it seems incredibly petty. If I just send a card, it seems cheap. I suppose I could send a card with $100 (I would probably give $200 to my nieces under normal circumstances, and her cousin is currently engaged, so Carrie would actually be getting an extra $100). Can you resolve this so that I don’t feel petty, guilty, or taken advantage of?

A: You’ve had 15 years to speak to her about the loan. You should have brought it up with her at least 14 years ago! It would have been a pretty easy and straightforward conversation: “Is now a good time to pay me back the $200 for that vase? If not, let me know when you’ll be able to; I’m happy to draw up a repayment schedule if installments would make it easier.” You can, in fact, still have this conversation with her—but there’s no reason to attach that old loan to her wedding. If you’re not invited to someone’s wedding, you’re under no obligation to send a gift, so there’s nothing cheap about simply sending her a card wishing her well. You’re right, though, that bringing up $200 she borrowed from you as a recent college graduate in a supposedly congratulatory card would be needlessly petty, passive-aggressive, and cream-spoiling. Send a nice card offering your best wishes. If you think you can swallow the loan—it was $200 15 years ago, and it doesn’t sound like you need the money—I think that would be ideal. If you can’t, then wait a reasonable interval after the wedding and raise the issue calmly.

Q. Ex-boyfriend turned friend with benefits: I dated a man for a few months last year. He broke up with me in early January, citing differences in relationship experience due to our ages (I’m a woman in my early 20s, and he’s in his mid-30s). I was gutted. I believe(d) I love him, and, quite frankly, he’s one of the most handsome and smartest people I know. I’m not too hard on the eyes myself, and we match each other career- and intellect-wise. The breakup was a complete surprise, to say the least. Nevertheless, after a period of no communication, we have now been flirting and getting on almost as we used to when he was still courting me. And usually he initiates this behavior. More recently, we started hooking up again. The chemistry is all there, and it’s undeniable that we value each other more than just as cheap thrills. And, for what it’s worth, he said he hasn’t had sex with anyone else since breaking things off with me (hallelujah). What boundaries need to be in place with this new situationship? We really do care for one another, and I can’t help but still see him as the man I fell for in the first place.

A: Hooking up with someone who broke up with you and whom you still see as the man you love, who treats you largely the same way he did when he was formally dating you but without that same former sense of commitment and shared expectations, strikes me as a recipe for heartbreak! You are allowed to break your heart over him, of course, and if you want to keep seeing him, you certainly can. I’m a little bit unsure if he broke up with you in January of 2019 or 2020, but I don’t suppose it matters much either way, since the main problem still remains. This situation seems ripe for a conversation! “You say you haven’t been seeing anyone else since we broke up, and I still have really strong feelings for you. Do you want to get back together? Because I do.” My concern is that you have avoided asking him this question because you fear that his answer will be no, and you’d rather keep hooking up with him without requesting clarity in the hopes that he’ll eventually find you so charming, so lovable, so easygoing and fun to have sex with, that he will spontaneously say, “I was a fool. Will you go out with me again?” But even if he says that he doesn’t want to get back together, it’s still a conversation worth having, because at the very least you’d have a more honest and clear hookup arrangement, where both of you know exactly what you’re getting into.

Q. Just let me pay: What are your thoughts on the etiquette of offering to pay? I make more money than many of my friends and family, and when I dine with them, I often offer to pay and mean it. I want them to know that I’m not just trying to be polite—I actually would like to pay. But I also don’t want to offend anyone and act like I think I’m Richie Rich.

A: I think offering to pay for dinner is charming! I enjoy doing it, and I enjoy accepting it. If your friends and family are reluctant to take your offer at face value in the moment, you can always bake the offer into the initial invitation: Make it clear that you’re inviting them out to dinner or a movie or a show as your guest and that you’d love to cover their share of the expenses. If they need additional reassurance, you can tell them that it would bring you joy and they can rest assured they will delight you if they accept your offer. If the friendship is old enough, or the family relationship solid enough, you can also turn it into a bit of a game by calling the restaurant in advance, giving them your card, and letting the staff know that under no circumstance are they to accept your guests’ attempts to pay their own way.

Q. Re: Sister’s boyfriend’s twin: My grandmother and her sister married brothers. I might wait to do much until after the wedding because if you have a couple of dates and it blows up, you don’t want that at the wedding. But it’s not that weird.

A: That’s a good point! If the wedding is in a few months, it can’t hurt to wait. But if it’s still a year or two off and you feel confident in your ability to handle rejection with aplomb, go for it.

Q. Re: She’s still doing the fam thing with the ex: It sounds like the writer realizes he doesn’t want to be in a relationship with his girlfriend anymore and is trying to find a way to blame her. Don’t do that—own your choice and why. It’s fine to not want to be with someone anymore, but if you are going to try and frame it like she did something wrong so you can have a more “clear conscience” about ending a relationship, that is pretty unkind.

A: That’s a helpful reframing. “I don’t want to be with someone who’s raising a kid” is a perfectly good reason to end a relationship, but I also imagine it might challenge one’s sense of self as a “good partner” and that one might, as a result, attempt to justify that choice with language like “She’s not mother of the year” and “They’re perpetuating a harmful myth of family togetherness.” It’s really not that complicated. She’s co-parenting her kid in a way that doesn’t involve you. You don’t actually want it to involve you; you want her to be less involved in her kid’s life or you want to stop seeing her. The correct choice is to stop seeing her!

Q. Re: Ex-boyfriend turned friend with benefits: Prudie’s advice is on point here, but I want to add, from experience: Don’t do this! I’ve tried things like this and seen friends try it. It doesn’t work out, and it slowly eats away at you as you know you’re settling for less than you need. The women I know who are in strong, healthy relationships have all gotten there by daring to ask for what they want and knowing they deserve it. It’s hard and scary, but you can do it.

A: If this were the sort of situation where the breakup had been mostly mutual, or long ago enough that neither one still carried a torch for the past, I think it could work—I’m by no means against hooking up regularly with an ex—but this particular arrangement, and the obvious one-sidedness of the romantic investment, strikes me as emotionally dangerous. This ex certainly seems to like the letter writer, but he seems, at the very least, careless of her feelings.

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Classic Prudie

Q. I’m worried my ex-dominatrix sister may have molested my son: My sister used to be a professional dominatrix. She was quite open with me about this and said that she stopped because she was tired of being “topped from the bottom”; she wanted “real” control. We haven’t discussed this for some years now, and it never occurred to me that it might not be a good idea to leave my preteen son alone with her. The other day, I arrived early to pick him up, and it took my sister a while to answer the door. It appeared that she and my son may have both hastily put their clothes back on. I later asked my son what happened in general terms, so as not to sound accusing of anyone. His answer was plausible, but it almost sounded rehearsed. I’m not sure what to do. Maybe nothing untoward happened and I’m just being paranoid. I love my sister, and I really think she would know better than to do anything remotely sexual with her nephew or anyone his age. Should I talk to my sister and hope she can assure me that everything’s OK? Or should I just assume the worst and never again leave my son in her care? Read what Prudie had to say.

Danny M. Lavery’s new book, Something That May Shock and Discredit You, is out now.