Dear Prudence

My Family Won’t Impose Boundaries on Our Creepy Neighbor

They say he “lacks social skills” and that there’s nothing they can do.

On the left, hands holding out a present. On the right, a woman looking skeptical.
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Dear Prudence,

I am a thirtysomething who recently moved into a family-owned property out of necessity. My parents have been great about this, and I’m glad to be here. There is, however, one issue: a family acquaintance we’ll call “Moe.” I never liked Moe growing up. He gave me (and others) many unsolicited gifts and asked me to do projects for him. None of the gifts were themselves inappropriate, but the pattern of favors and obligations made me uncomfortable, even as a child. I decided I didn’t want to speak to him after he tried to date another family friend and didn’t take no for an answer. She had to basically cut him out of her life. His lack of boundaries is obvious. He continues to “gift” people various items that they neither want nor can actually store, seemingly also unaware that this is reckless behavior during COVID, and drops by other people’s houses randomly. My parents recently told me that he drives by my house at least a few times a week, to “see if they’re around.”

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I’ve tried to talk to my family about it, and I get told that he “lacks social skills” and that there’s nothing they can do. I know some people have tried to implement boundaries, but I don’t know if they’ve stuck to them or if they ended up letting him back into their group. I do not want to start dealing with random “gifts” on my porch and really don’t like the idea that someone is scoping out my house for any reason! I feel comfortable telling him off—but what can I do to get my family to impose some boundaries and regain some sanity?

—Family Friend Isn’t Mine

There’s an important distinction to be made between “social skills” and “taking no for an answer.” You’re right to be skeptical of your parents’ implied assertion that because Moe “lacks” something as vague and potentially wide-ranging as “social skills,” they can’t be expected to set reasonable limits with him like “don’t drive past my house to see if I’m home—call or text if you want to arrange a visit instead.” But don’t waste your time and energy trying to persuade your relatives to set boundaries they may have no interest in setting. This sounds like a long-standing pattern on both sides, and they may be as invested in giving him his way as he is in having it.

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The good news is that you’re comfortable with the idea of telling him no yourself, which is a great place to start. While you don’t need your parents’ permission to set a guest policy of your own, you ought to give them advance notice so that they don’t unknowingly undermine you, should Moe attempt to circumvent you by asking them for continued “permission.” Tell them you’re going to let him know you don’t want to receive any gifts and you don’t want him stopping by the house unannounced, and then do so. If they refuse to back you up, at least you’ll know you can’t count on them for support and can act accordingly. They may never choose to set limits with Moe, but that shouldn’t stop you from setting limits of your own.

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Help! I Feel Like I’m Always Competing With My Boyfriend’s Flirty Best Friend.

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Dear Prudence,

I live with my primary and secondary partners. My primary partner, “Taylor,” sees my secondary partner as a best friend—with some boundaries blurred, as we share a very small apartment and a bed, and they both get along incredibly well. At one time, the two of them considered dating, but Taylor wasn’t feeling it and called it off. At least, that’s what we thought. My secondary partner, “Demi,” refers to both me and Taylor as her partners. That could be fine, because Taylor isn’t uncomfortable with the term, but I’m pretty sure Demi thinks the two of them are still dating. I’ve pointed this out and made space for them to talk about it without me around. Taylor says they’ve “had the talk” a few times now and if it’s not sticking, it just won’t, and now isn’t the time to bring it up because we don’t have the chance for space because of the pandemic.

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I know that Taylor eventually wants to live just the two of us. Demi moved in with that knowledge too, but if she thinks all of us are dating, she might be thinking that’s not the case anymore. I don’t really mind living together as the three of us, but my priority has always been Taylor, something I’m pretty sure I’ve been clear on as well. I really don’t feel comfortable saying, “Hey, so, you know, you and Taylor aren’t together romantically, right?” But I also feel uncomfortable having this knowledge. What’s my obligation here as a partner to both? Do I force them to talk? Leave them to make their own decisions? We won’t be able to move to a bigger place for a long time because of prices in the state we live in, and I’m pretty terrified of conflict. I know that I’m definitely doing something wrong here, but I can’t figure out the right way to untangle this mess, or if I should even be the one untangling it at all.

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—Not a Throuple

It’s one thing to know you’re terrified of conflict and to treat your own fears compassionately and humanely. But if you indefinitely attempt to stave off a necessary conversation about shared expectations, you will be setting yourself up for a much more serious and likely unavoidable conflict further down the road. You should treat your fear of conflict as something that requires conscious management, rather than an immutable feature of your character. You do need to talk to your live-in partners about your plans for the future, especially as they relate to living together and what the word partner means to each of you. But—and I hope this can relieve some of your anxiety—that does not mean you and Taylor have to have a joint break-up session tomorrow. It’s very possible that Demi understands her partnership with Taylor to be different from her partnership with you. Since both Demi and Taylor live together, get along well, and share a bed and a romantic relationship with you, it’s understandable that Demi would frame that as a partnership—albeit one that no longer includes sex—especially since Taylor seems fairly comfortable with the word. The important discomfort here is yours, and that discomfort can be addressed fairly straightforwardly by seeking clarity. That may include the possibility of conflict, but not automatically so, and it’s simply not possible to avoid all conflict forever. The upside of getting through conflict, even if you fear it, is that you don’t have to live with that uneasy feeling in the pit of your stomach that accompanies thoughts like “I think I’ve been pretty clear.”

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The first order of business is to speak to Taylor. What “isn’t sticking” as a result of their conversations with Demi? Is it simply Demi’s use of the word partner, or has Demi asked for something in terms of intimacy, commitment, or attention that Taylor isn’t interested in giving? What does “eventually” mean to Taylor when it comes to living together just the two of you? Does Taylor expect that you’ll keep seeing Demi after you stop living together, and if so, would Taylor be interested in maintaining an independent friendship? You say that Taylor has always been your priority, but it’s not clear how far that priority extends, or if you’d rather live alone with Taylor too. Would you, for example, want to keep dating Demi even if Taylor didn’t want to be part of her life anymore? There are practical considerations too, like when your lease is up, and discussing your future living situation together is something you three would have to do even if you were all just roommates. Once you and Taylor have a clearer sense of when you’d like to start living as a duo again, you can talk to Demi together. Ask her what she wants, avoid making assumptions, don’t apologize for the mere possibility that you might want different things, but give her space to have her own feelings too. If the idea of having a frank, loving, open conversation with your partners about the future feels terrifying and like an unacceptable level of conflict, it might be time to revise your definition of conflict and figure out how you can better manage your anxieties.

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Dear Prudence,

I recently celebrated my 15th birthday. My grandparents, who decided I am ready for more responsibilities, gave me an iPhone XR equipped with cell service, which I can start using once it makes sense to (basically, after the vaccine). I really appreciate their generous gift and am impressed with the phone’s features, but I’m perfectly happy with my current phone, which I only got back in July. I was hoping to just ask them to return the gift and give me money for something else instead, but the more I think about it, the more I remember how excited they were to give it to me. I’ve asked to return gifts of much less value from them in the past, and they were quite upset then, so I don’t know how they’d react if I asked them to return something so expensive. On another note, my grades have been slipping this past year (as I’m sure many others’ have), and though I know I’m doing my best, I almost feel like I don’t deserve such a nice gift. Should I return it and face the backlash, or wait to use it until I’m ready?

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—Is There a Receipt

The question of guilt is worth addressing first. As you say, you’re far from the only student who’s been struggling during the pandemic, given how much additional stress, anxiety, inconsistent Zoom connections, and the like that you’ve had to deal with while you try to attend classes. If a relative wants to give you a gift for your birthday as a gesture of affection and appreciation, that’s a good thing and not something you should feel guilty about because you don’t have perfect grades. I realize feeling guilty isn’t something you can simply switch off through sheer force of will, but try to take it easy when you’re inclined to beat yourself up for being human and having a hard time.

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As for not knowing how your grandparents would react if you asked them to return this gift and give you the money—well, I’m afraid I have less heartening news there. If they were “quite upset” when you asked them to return a sweater, they’ll almost certainly be quite upset if you ask them to return an iPhone, so I don’t think you’re going to have much luck there. You don’t say anything about your parents, but if you have a good relationship with them, you could try telling them what you’ve told me and asking for their help. But I suspect the best you can do is try to let your grandparents know what you’ve got your eye on for your 16th birthday a few months in advance, hope for the best, and say, “Thanks, I love it,” whatever they get you.

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