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Hello my darling nieces and nephews, and welcome back to my digital living room. It’s been a whirlwind 17 months, and I’m very happy to be able to address your woes once more. Let’s get started, shall we?

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Hello Dillon! I have a friend who doesn’t make a lot of great decisions, and she loves to tell me about her problems and sometimes asks for my advice, but if I ever give her my opinion she gets really upset with me because I don’t tell her what she wants to hear. It’s becoming a tireless, endless cycle. What should I do?

Sometimes people may seem like they’re looking for advice, but really they just want to feel heard. If your friend is consistently getting upset with you about your responses, it might be best to let her speak and then ask if she wants your opinion. In the end, it’s her life to live and her decisions to make, so you don’t need to try and solve her problems in any way. If you think it’s necessary, it would be perfectly reasonable for you to ask her not to come to you so often with her sticky situations.


I’ve been with my boyfriend for over a year and a half now. He lives with his lifelong best friend and three other close friends. They are kinda socially awkward but have all moderately warmed up to me being around except for his best friend. He won’t talk to me unless prompted, and when it’s just me and him in a room we just ignore each other. It’s frustrating because I’ve been around for a long time now, and he still won’t even exchange pleasantries or acknowledge my existence. I feel super awkward trying to initiate conversation because I don’t know him super well, and he has an air of judgement hanging about him. What do I do Auntie Dill?

If you haven’t already, I think a good first step would be to talk to your boyfriend about this issue. Is his best friend like this with all strangers? Since you say they are “lifelong” best friends, he might be able to offer some insight into this behavior.

You are right to be upset about this — while you can’t expect to be best buddies with him, it seems like his behavior goes beyond awkwardness and lands squarely in just-plain-rude territory. Unless your boyfriend indicates that this is all some big misunderstanding, the best course of action is to spend as little time around his friend as possible.

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I have a problem saying no to people, and I always end up taking way too much on my plate in order to help others, usually at my own expense. How do I balance my desire to be helpful with my individual responsibilities?

Sometimes, our ambition can get in the way of looking out for our own health. I understand the impulse to give as much of yourself to others as possible, but the truth is when we over-extend ourselves to the point of exhaustion, we aren’t very helpful to anybody. It’s not your responsibility to shoulder the burdens of others, and nothing is going to fall apart if you take a step back to realign your work-life balance. Almost everyone will be very understanding if you tell them you need to scale back your commitment to things, and those who aren’t don’t deserve your consideration in the first place.


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