Dear Prudence

Help! My Boyfriend’s Sister Demanded We Move Our Proposal So She Can Get Engaged First.

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

A monthly planner with a graphic of an engagement ring.
Photo illustration by Slate. Photo by 2H Media on Unsplash.

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

Jenée Desmond-Harris: Hi everyone. This is my last chat before I take off for parental leave, so let’s make it a good one.

Q. Can’t we just be happy? Me, my boyfriend (“John”), his older sister (“Katie”), and her boyfriend (“Tom”) are all between the ages of 28-31. Katie has always been an overly competitive big sister and jealous of John’s easygoing and likable nature. As an adult, Katie very much “has everything” but seems unhappy and overall insecure about her outwardly extremely successful life. I’ve worked hard to establish what I thought was a good relationship with Katie; she is not an easy person to get close to but it’s important to me that we at least feel comfortable around each other, and it would mean a lot to me if we could grow to be friends in the coming years.

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In January, John and I made plans to get engaged on a meaningful trip in May. John clued his parents in, and that info made its way to Katie, and she is livid because in her mind John being engaged before her is…him winning? At life? Or something? Katie threw an astounding scene and made their mom call John and ask him to move our engagement months later so that Katie and Tom could have time to get a custom ring made, make an elaborate engagement plan, and propose before our trip, even though this is bad timing for them as Tom just started a new job, they just moved, and they’re about to get a puppy that will require a lot of work.

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John was hurt that he would be asked this when everyone involved knew we had set-in-stone plans, and because our engagement is about us and has absolutely nothing to do with Katie. John informed his mom we are not changing our plans. But now John has been told he has to call Tom and tell him our exact plans down to the day to ensure Tom can get his act together at least a day before John proposes. This is so, so ridiculous to me. I have offered to delay any announcements outside of my close friends and family by a couple weeks if that would ease tensions, but apparently that’s not good enough.

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I can’t emphasize enough how much we don’t care what Katie and Tom do, but I still can’t help but feel like no matter their outcome, I’m being set up for everything to revolve around Katie. I want to feel excited about my engagement but now I’m just dreading the tension that will come with planning a wedding around what may or may not hurt Katie’s feelings. Based on Katie’s personality, I knew there was a possibility of this happening all along, but I was not prepared for the level of drama going on right now. How can I find some peace of mind through all of this? I’m afraid the tension will come through when I talk to my friends and family about our plans, and I will seem like I’m not in fact excited to be marrying the love of my life. Should I try to have a heart-to-heart with Katie? I’m afraid it would go poorly.

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A: The first part of this that’s making my head spin is the idea of announcing a plan to get engaged. At least for most Americans who aren’t tapping into cultural traditions based in other cultures, the engagement itself is usually just the announcement of the plan to get married, is often a surprise to one of the people in the couple, and is almost always a surprise to everyone else. Bringing John’s parents  into the mix so early in the process was the first mistake. But here we are.

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I originally thought I’d advise you to stick with your initial response: “We are going to get engaged on our schedule, but we’ll hold off announcing to the family until after Katie announces if that would make her feel better.” But you know what? That’s nuts. And it feels like it would set a precedent for your accommodating ridiculous demands, which will not end with this and will only become more unreasonable as both weddings are being planned. The great news is that John is already inclined to stand up for himself (and for your relationship) here. Encourage him to continue repeating “our engagement is about us and has nothing to do with Katie.” He can even add “we’re excited to celebrate with her when the time comes—it’s going to be a great year for the whole family.” Just refuse to debate or engage beyond that. Don’t fight, don’t negotiate, don’t get into screaming matches, don’t be cold or weird to Katie, don’t give them anything legitimate to complain about. You can’t control how they react, but you just need to reaffirm to yourself (hopefully with the support of friends and other reasonable people in your life) that you’ve done nothing wrong. Because you haven’t.

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And let John continue to handle the communications with everyone in his family. Katie hasn’t said anything directly to you, so you shouldn’t feel pressured to say anything directly to her. Are they going to be upset about the way you’re handling it? Maybe. But you and John owe it to each other to refuse to take this demand seriously, refuse to give it more of your energy than necessary, and refuse to allow it—or the hurt feelings around it—ruin this special time in your lives. Meanwhile, you’ll be teaching his family an important lesson about what happens when they get together to bully you: They can cause a scene if they want, but they’ll be wasting their time.

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How to Get Advice From Prudie:

• Send questions for publication here. (Questions may be edited.)

• Join the live chat Mondays at noon. Submit your questions and comments here before or during the discussion.

Q. Happy in my skin: I am 15 and am an avid runner and work out every day (most of this is for school sports but I still enjoy working out on weekends). I am rather small and skinny for my age, although I am extremely healthy and eat what I want on a regular basis.

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Recently my dad has started to get on my back, telling me that I am too skinny and that I must have an eating disorder. He says that I never eat (which is not true) and that my body is extremely unhealthy. This is so ironic because growing up, he constantly told me that I was getting too chunky and needed to lose weight, and he is morbidly obese. I am the youngest of three and know for a fact that I am the only child getting any of these comments. I also have cystic acne (inherited from my mom) and although I wash my face and have a doctor-advised skin care routine, I get the occasional large cyst on my face that looks like a massive pimple. While I do not see any issue with it since I am doing everything I have been told by doctors and it is common in my family, my dad thinks these pimples are the end of the world and that it is my fault I get them.

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Although I try not to listen to his constant criticism of me and my body, I am extremely hurt by his constant comments about how my body is not good enough. The fact that this has been going on since I was 7 makes me angry that at such a young age I was subjected to his body shaming. I am happy with how I look and am extremely happy that I am healthy in my body. Is there any way I can stop his criticism? I am afraid that if I ask him to stop, he will gaslight me into thinking that he is doing what is best for me and just trying to help, but his comments make me angry and depressed at times. Please help.

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A: I’m writing not so much because I have a great answer for you, but because I’m so impressed that you are able to see this situation for what it is: one in which your dad is mistreating you for reasons that aren’t rational and are based on his own issues. By understanding that he’s the one with the problem and not internalizing his negative messages about your body, you’re already winning. It’s definitely worth telling him that while he may believe he’s doing what’s best for you, his comments are hurtful. Maybe even recruit your siblings to back you up in asking him to help.

But you’re right to be prepared for him to be self-righteous and defensive. As a teen, your options are so limited when it comes to pushing back against your parents’ behavior—and that’s extremely frustrating. My best idea is to think about where you learned that your body and face are fine the way they are and that body shaming is wrong. Was it school, or friends, or the internet? Whatever the source, turn there for affirmation or reinforcement of your beliefs as often as you can over the next three years. I’m really sorry you’re dealing with this and I’d love to know if readers have any other ideas that might help you out.

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Q. Traveling trouble: I ended up winning a contest for a trip to my dream country. I was so excited, but my boyfriend ran kind of hot and cold. He hasn’t traveled like I have and doesn’t love it like I do. I realized that I could upgrade the trip and go by myself, which is what I did. I had a blast.

My boyfriend was livid. He called me a horrible girlfriend for leaving him at home. I said I didn’t want him dragging me down on this once-in-a-lifetime trip. He said if we wanted to be serious that he shouldn’t be left behind because he wasn’t going to be 100 percent perfect all the time. I told him he was being a selfish brat and left. We haven’t talked for a week. I feel like I can’t get my head around this. Was I being the selfish one or is he being unreasonable?

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A: If the plan was for him to go, and you uninvited him because he showed a little ambivalence, that was kind of messed up! At the same time, it sounds like you have some incompatibility, you’re both calling each other names, your communication sucks, and you resent each other.

With that in mind, you know how you made the quick decision when it came to the trip that being by yourself would be an upgraded experience? Do the same when it comes to your relationship.

Q. Podcast or pod can’t: My friend “Steve” and I have known each other for more than a decade, and we started recording a weekly podcast about a mutual interest six years ago. Steve and I have had a close bond over this shared hobby since high school, but our personal lives have diverted significantly.

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My wife and I own a house, and I work 50-plus hours a week at a white collar job. After a semester at one MFA program and completing his degree at another, Steve lives rent-free in the equivalent of a one-bedroom apartment in his parent’s basement, and he doesn’t believe in work (his words).

While I enjoy my friendship with Steve, preparing for a weekly podcast has become more taxing as my career has progressed. Now my wife is pregnant, and she (understandably) expects me to adjust the time I spend on my hobbies—including the podcast.

But I’m concerned how this will impact Steve’s struggles with mental health. He’s received varying degrees of treatment for depression over the years, and he’s said on multiple occasions that he views our friendship as a lifeline, specifically our weekly call to record the podcast.

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What do I owe Steve? At this point in my life, it would definitely be a relief to reduce our podcast to biweekly or monthly or retire it altogether, especially with a baby on the way. But I’m concerned about how this will affect my friendship with Steve and his mental health.

A: You’re such a good friend to Steve! But being responsible for his well-being puts you in a really difficult position that’s not fair to you and not sustainable when it comes to his long-term health. The answer to “What do I owe him?” is kindness, empathy, and clear communication. But, especially when it comes to your precious time, you do not owe him more than what you owe yourself and your family. So this is a perfect moment to give some serious thought to what works best for you.

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Why don’t you sit down with your wife and figure out what recording schedule would  make sense once the baby is born? Or maybe the answer is that, totally separate from whatever she might request, you just don’t want to do this podcast anymore. Either way, make a decision and then tell Steve as soon as possible, giving him as much warning as you can before you make any changes. I’m not sure how far along your wife is, but maybe you could even give him a few months’ notice so he has time to get used to the idea. Tell him you would support him in finding another co-host to cover the weeks that you don’t record, or take over for you completely. Most importantly, make sure he understands that this isn’t personal, and that you will still be friends and discuss what’s going on in your lives and your hobbies.

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I know what you’re afraid of: That no matter how kind you are, this news will plunge him into a deep depression. I hope that doesn’t happen, but it’s possible. Make a plan for what you’ll do in that case, whether it’s nudging him toward adjusting his medication or touching base with his parents to make sure they’re aware of what he’s going through, or checking in regularly to offer a listening ear. Providing this kind of support, more than hosting a podcast that doesn’t fit into your life anymore, is the right role for a good friend.

Q. Re: Can’t we just be happy? Katie will always be in competition with you and John. From here on out, you cannot share plans about the wedding with her. She will try to outdo you, she will steal your themes and venue, and God forbid if you try to get married before her.

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Word of warning: If you tell her what you plan on naming your future children she WILL “steal” your baby name.

A: This is 100 percent exactly what will happen! Or better yet, she’ll accuse you of having stolen her baby name that she never mentioned.

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Q. Re: Happy in my skin: I am glad you are happy in your skin. But I would feel better if you would schedule a doctor’s visit and discuss your body with the doctor. That will give you some validation and facts from a professional to use with your father.

I did see a few red flags: Because eating disorders can begin with a parent criticizing a child for being “chunky”, your father put you at heightened risk for eating disorders. The references to being an “avid runner” and working out every day and eating “what I want” are general enough to be within the bounds of healthy, but could also be benign sounding code words for an eating disorder. See a doctor, get help from a school counselor, therapist, and other adults for dealing with a parent who is not giving you the love and unconditional support that you deserve.

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A: That’s a very good idea: Seek out a counselor or other professional not to treat the problems your dad thinks he sees with your body and your skin, but to cope with the relationship you have with him. And if there really is an underlying issue, it will come up and be addressed.

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Classic Prudie

My live-in boyfriend of almost three years is amazing—when sober. When drunk (about once or twice a month), he’s belligerent, disrespectful, and hurtful. He’s been reconfiguring his life path over the past year after having had most of his goals on the back burner, one of which was getting in shape, and he’s put himself on a strict diet and workout regimen. I’ve been trying to support him but have made some mistakes, like continuing to have cheesy foods around for snacks or insisting on making birthday cakes for him and his family members. He’s been trying to get me to join him on the regimen—I follow it when we’re eating the same meal, but it’s hard to keep track, so occasionally I’ll screw up and make pasta for both of us without thinking about it. Last night, not for the first time, he turned an innocuous comment I made into a critique of my weight.

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