If you can't rely on them telling you, how do you know what people want?

I wouldn’t say anything. I understand your concern, but most likely she very much enjoys time with you. When the right opportunity comes up you can reassure her that she shouldn’t feel obligated to spend time with you and miss out on something she would prefer to do, but also she should know how much you enjoy being with her.

Maybe you can talk to her about your own experiences when you followed what you wanted to do, or not listening to yourself when you didn’t want to do something, and some of your regrets about it. Then it’s not a lecture, but more a sharing of life experience. Another idea is when she needs to cancel be sure to let her know it’s no problem at all and be excited and interested in what she is doing instead.

I think this sort of thing is so tricky. Teenagers especially assume incorrectly what adults are thinking. Even as adults, in adult relationships, assumptions of this kind and miscommunication are the source of discord and discontent.

You strike me as quite perceptive and certainly a caring person. I think you’d pick up on any reluctance to come and stay or that she’s just coming because she thinks you want her to. You could always wait for an appropriate moment and make it clear to her that you enjoy her staying over but that you understand she’s getting older and that you’ll understand if she ever wants to stop the regular visits. Just make it clear, you’re not suggesting that she stops but that she should feel comfortable about telling you if that should ever happen. Just keep it light. I really do think you’ll be able to sense if she’s only coming because she feels you want her to.

I’m going to add that I loved spending time with my big sister when I was younger. I definitely had her on a pedestal and I enjoyed her company very much. So, enjoy this special time while you both have the freedom to be together.

I understand your concern – and your reluctance to say anything. But many a tradition (and relationship) have been painfully tolerated for many years for fear that ending it would be just too painful for the other person. In doing so, the desire to not hurt the other person results in a kind of lie, which can be cancerous to any relationship.

What if you look at it this way: you love your sister too much to lie to her. The truth here is that you enjoy spending time with her, but would never want her to do it out of obligation. You can keep it honest without making it heavy.

And keep it from being a “speech”. Keep the focus on just opening up a channel of communication with your sister that is reciprocal and allows for pure honesty from both sides. It’s a liberating thing to know that you have a relationship with someone that doesn’t require the nervous accumulation of white lies that are born of repeated sparing of feelings. Be clear that your relationship is strong enough to withstand a disappointment – but can be weakened by a lie.

It gets complicated with perpetual people-pleasers, however. In my experience, their own desires get tangled with perceived desires from others. It becomes difficult to understand your own wishes and desires.

Personally, I find that asking a question or two is a much more successful technique than making statements. Don’t wait until the issue carries too much weight.

My daughter and I had this experience recently. Each of us misread the other until we started to ask questions.

I agree that speechifying doesn’t work, for either party.

I would leave things be. Your sister apparently is living on her own and it has to be helpful to her to have you as an anchor of support. This arrangement is not likely to last that long. At some point your sister will want to live more independently. Make sure to let her know that she can always spend the night, no questions asked.

This arrangement will probably end when college, a full-time job, a serious romantic partner, or some other normal development crowds it out. In the meantime, enjoy it and don’t overthink it. She’ll end it when she’s ready. If she doesn’t like it anymore (which seems unlikely), part of growing up is figuring out how to deal with this interpersonal stuff.

Thank you, all. I’m going to weave the topics rituals, growing up, and honesty in general into one of our conversations. I won’t address the sleepovers, specifically, but I’ll try to make sure she feels comfortable telling me when things change there. I’ll keep things light, but I’m sure she’ll understand what I’m saying. She’s very much a social person, extremely perceptive in these things.

Appreciate your input a lot, jellies!