Dear Darling Advice Column
Darling’s outlook on life, relationships, conflict, and crime can best be described as whimsical. She values care for self and community, feeling good, looking good, and fucking s@!* up. There are no questions too bold, topics too old, and anything you’re thinking is conversation gold.
Send your ponderings, your questions, and your deepest darkest fears and desires to our dear Darling 😉
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Dear Darling
Dear Darling, I have a best friend who is kind and wonderful and beautiful and amazing. Our relationship is everything to me. We've been friends since elementary school, and have kept in touch despite going to different high schools and colleges, and we facetime...
Dear Darling: Attempted humor
Dear Darling, Sometimes I like to take old jokes that are in bad taste in their original form, blonde jokes for example, and change them so they're about specific politicians rather than picking on generalized groups. Is this problematic? From, T. Peaches Wilkerson...
Dear Darling — February 2026
Dear Darling, I have a roommate who will not stop talking to me very loudly about the same topics I do not care about in great detail. I can't go into the common areas for more than a minute when they're home without them coming out of their room to talk to me. It...
Dear Darling: Anxiety or Reality?
Dear Darling, I feel like like a lot of my friends hate me, which is something I've always struggled with, but in some cases I've been right. Lately its been really bad. I tried to tell a friend I was having a bad week and she just stared at me. Other people in...
Dear Darling: Why keep moving if nothing i do matters?
Dear Darling, I feel like I'm going, to use a child friendly word, fluffing crazy! Every time I sit down to get work done, I think, "Does this really matter? Am I really doing anything that's really, truly important in the world? Am I simply a hamster running in its...
Dear Darling: Meet the Parents except it’s poly and they’re you’re extended anarchist community
Okay, darling. I like to date my coworkers (that’s not the problem) and always struggle with gauging when it’s a good time to bring them to community events. You know the kind - when everyone you know is tabling for something, and the whole event is spent seeing your...
Dear Darling,
Dear Darling, I'm gonna be blunt with you: I saw someone the other day with the most amazing ass that I've seen, maybe ever, and I can't stop thinking about it. It's not like me to be so fixated on someone's anatomy as a source of attraction. Normally I'm downright...
Dear Darling: Friendship Advice
Dear Darling, I have a friend who feels like a stranger now. We still eat lunch together, talk, and smile at each other, but it doesn't feel like there's anything left of substance. We're part of a friend group of four, and she's definitely close to the other two than...
Dear Darling: growing? up?
Dear Darling, I need advice about how to talk to my partner about my secret immature thoughts. because we've been together for quite awhile, i have already established a pattern of keeping them to myself. But sometimes i get pretty insecure about things, or really...
Dear Darling / May 2025
Dear Darling, "Why is the sky blue" has become offensive and, at best, assumed a joke. When we stop to consider what we might about someone in this position, we find the vulnerability, we find a scared person looking for affection. To compete with a what will not only...