Help! My Messy Sister Is on a Mission to “Take Back” My Husband. What I’m Planning in Return Will Ruin Her Life.

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My husband used to date my older sister, “Rochelle,” when they were in college (back then I was in high school and only met him briefly twice). It didn’t work out due to her numerous substance abuse issues, plus her penchant for shoplifting. We ended up getting together when we ran into each other some years later while we were in NYC on business.

The problem is that within the last year, Rochelle has decided she wants him back and shows up drunk and pleading at our house at least once a week. Well, I had a baby last month and have reached my absolute limit.

I told my sister the next time she shows up, I’m taking out a restraining order on her. My parents, however, are begging me not to, as Rochelle has an extensive rap sheet that will weigh heavily against her if she’s arrested. I don’t want her in jail, but my husband and I are sick of the harassment. Should we just file it and let the chips fall where they may with her and my parents?

—Find a Life of Your Own

Dear Life of Your Own,

Has your sister heard your husband say “Please leave and never come back. You’re not welcome here and this is not okay” loud and clear, before shutting the door? I just want to make sure he’s not engaging with Rochelle when she shows up, or trying to be nice about this.

Beyond that, I’m sure your parents’ hearts are breaking over the way her life has unfolded, and I understand their desire to protect her. But it sounds to me like she is in a really bad place and will probably get herself in trouble with the law again pretty soon regardless of what you do. Gently share that idea with them, explaining that your getting the law involved (or not) probably isn’t the thing that will determine whether Rochelle’s life improves. Then, suggest that all of you start to think about whether there’s a way that you can get her some help with her drinking and/or the emotional or mental health issues that have likely fueled her behavior for so many years. Have that conversation soon, to plant the seed that she needs more than just your agreement not to seek a restraining order. She needs to become a person who doesn’t feel the need to do things that justify restraining orders! Tell them you’ll revisit the issue with them when you’re three or four or five or six months postpartum. Because you definitely don’t have the time or energy right now.

In the meantime, your husband can work on documenting Rochelle’s appearances at your home and looking into attorneys who might be able to help you if you decide a restraining order or order of protection is necessary. But before you seek one out, try a simpler solution that won’t cause your parents to fret: Turn the baby’s white noise machine all the way up and don’t answer the door.

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I am having a bit of a disagreement with my partner (both women) about my generosity and general people-pleasing tendencies, and I was hoping for an outside perspective on the issue. I am a highly productive type-A sort of person who is generous with my time and resources. I was raised to treat others the way I want to be treated, and I would like it if my friends, family, and coworkers were more generous and thoughtful towards me, so I try to lead by example.

Unfortunately, I find myself giving much more than I receive or am offered, whether it is paying for dinners/drinks, doing favors, or extending invitations. This often leaves me feeling a bit taken advantage of, and questioning whether people truly like me, or just what I can offer them. My partner thinks I should just “do less” to address this imbalance, as she feels people either can’t or won’t step up and do more. But this isn’t really who I am, or how I want the world to be. I am also fortunate to be in a better position financially than many, and my type-A never-sit-still productivity means I have time and energy to offer as well. I would be happy with people giving where they can, whether it’s a text to check in, inviting me to socialize, or contributing time or money however they are able. She thinks I just need to lower my expectations and offer less, but I would feel bad saying no, especially since I have the resources.

What do you think—does my relative privilege mean I’m going to find myself in a lot of one-sided relationships, or is the problem that I am being overly generous and it’s unfair for me to expect some kind of reciprocity? For what it’s worth, this situation applies to my relationship with her as well, and my repeated attempts to ask her to be more generous have been shut down with the same “you should do less” response.

—Too Kind, Too Naive, or Just Blessed

When it comes to friends, family and coworkers, what if you were to give the same amount of time and energy, but more thoughtfully and intentionally? Choose the people who are really appreciative and who really need the support. Then, go all in. You’d be better off (and make a bigger difference) preparing dinner for a month for a friend who’s dealing with a serious health issue, or hopping on a plane to babysit for a cousin’s kids during a school break when there’s a gap in childcare, than baking a cake for every coworker’s birthday or paying every bar tab.

When it comes to your partner, I’m sensing that she might not be a great fit for you. There are many people who would love a generous, helpful, competent significant other with tons of love and energy to give, who would be happy to return those things, and who would be really empathetic about the struggle you’re experiencing. It doesn’t sound like she’s one of them.

Finally, it’s worth reflecting on whether your habit of constantly doing things for others is really a symptom of being type-A and having extra energy, or something else—like the belief that you have to earn your keep in friendships and relationships. Is there a part of you that thinks friends won’t keep you around if you’re not pulling out your credit card or showing up with a moving van and packing tape when they need to move? Think about it. And maybe experiment with how it feels to redirect your plentiful energy to tasks that make your own life better, or improve the world beyond people who you know personally.

My father thinks I hate him. That’s a wild sentence, I know. Let me explain further: See, my main route of showing affection is teasing. I like to play jokes with my friends; tease them for little mistakes (we all do it and understand it’s not mean-spirited), and as I’ve grown up, this teasing has transferred to my father.

However, at the same time, I don’t act this way with my mother, particularly because I don’t feel the same respect for her as I do for him. This lessened need for her approval means I often go to my mother for the hard stuff—I came out to her and asked her to tell my dad because her initial reaction meant far less than his and my anxiety would’ve killed me over the waiting process if I told him over text instead. (Note: There was no possible way they’d reject me, they’re both very liberal and didn’t mind at all; this was mostly my own anxiety gaslighting me.)

As prefaced by the start of this letter, my father thinks I hate him because of the teasing—I don’t know how I really explain to him that I’m not trying to slight him, I do it out of affection! He understands that I tease my friends out of affection, and trying not to tease him ends in a slightly stilted or quiet conversation because most of my humor does rely a tad on ribbing.

You have to know your audience. If your dad hates being teased, stop teasing him. Or at least cut back drastically. Get it all out with your friends and find a way to show your dad affection that makes him feel loved, not antagonized. It might mean you’re not being 100 percent authentic, but this is the kind of change you make for people who are important to you.

Catch up on this week’s Prudie.

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