Well, you didn't ask for my opinion, but...
Redoing other advice columns.
Welcome! I’m The Overthinker and this is a special edition of You Asked, an advice column. This week, I’m redoing a handful of other advice column answers that irked me. Have a question for The Overthinker? Send it to asktheoverthinker@gmail.com and it might be included (anonymously!) in the next edition.
“My Sad, Sad Friend Talks Only About Herself”
The Q: The letter writer’s friend is going through a hard time — and it’s been the only topic of conversation for months. “She manages to turn even the most pleasant interaction into something grim, cynical, and self-pitying. It’s getting to the point where I don’t want to be around her.”
The A, from James Parker at The Atlantic: Surprise her! Mix it up! “Crank up the gallantry, crank up the generosity: Send a spark of love and novelty into the black cloud.”
The Overthinker adds: You also. . . have to tell your friend what you’ve observed the last few months about her, about you, and about your dynamic — and how it’s come to make you feel. Your friend is clearly suffering, and instead of naming that for her at the outset, you’ve gotten stuck in a vicious circle of venting and resentment that is making things worse for you both.
Believe me. I understand how you got here. We live in what I’ve taken to calling an “interpersonally permissive” culture. We let other people do whatever they want, however they want to do it, without any face-to-face feedback — and then develop elaborate theories about what’s wrong with them with mutual friends and our own therapists.
I think there are a bunch of reasons why this is true: We filter a lot of our experience of other people through a lens of authenticity. “I have to let them be their true self,” we think. Even if that “true self” is, in this moment, suffering endlessly. We’re always being told to be empathetic — and we don’t realize we’re only empathizing with the part of our friend that would be hurt by our honesty, completely forgetting there’s a part of them that might be uplifted, redirected, or fortified by it. There is a real and pervasive fear of blowback (what if we’re wrong? What if we’re cancelled?). And many of us are simply out of practice with honesty. We don’t know how to begin, or even why.
But I’m quite convinced we need to turn the tide. As my friend Claire said: “If your friend has a horrible cough that won’t go away for weeks, you’d be like, ‘Go see a doctor.’ No question.” This is not so different! So gather your strength, and follow these instructions:
Separate your honesty from “the truth.” Going into this, you already have a theory about your friend (they’re depressed!), and you may well be right. You may also be wrong. Practice holding your truths lightly.
Share what you’ve observed with your five senses. Do so non-judgmentally, and with shared attention to your friend’s explicit behaviors, and your own. These details might include: a validating recap of everything bad thing that’s happened to them the past few months; a description of how you have observed them repeatedly turning your conversations back to themselves; an account of your internal thoughts and/or body sensations along the way (“I am noticing resentment building up in me” or “When you say X, my stomach tightens, and I feel what I think is dread.”)
Place your sharing in a framework of compassion. Receiving critical feedback is hard, and explicitly stating things like “I am sharing this because I really care about our friendship and want it to be solid” or “It makes me uncomfortable to speak up in this way, but I’m doing it because I genuinely hope it’s helpful to you.”
Offer any interpretations as just that — interpretations. If you feel the need to share with your friend your theory that they’re depressed, explain your reasoning. Have you experienced depression, or seen it in others? Just doing a lot of Googling? Explain how you got there, and express your openness to being wrong.
Return to your ask. Share that your goal right now is just to be heard and understood. Share that your long-term goal is for you and your friend to get back to more enjoyable, more wide-ranging conversations — and that you acknowledge that probably won’t be achievable today. Change takes time. We must have patience with the process, and we it’s totally fair to ask for reassurance that the process is actually underway!
“Help! I banned kids from my wedding. My sister keeps begging for an ‘exception.’”
The Q: “My fiancée and I decided on a child-free wedding. It wasn’t an easy decision, but with limited space and budget, we thought it was the best way to keep things manageable. We made one exception: my 8-year-old niece, who’s going to be the flower girl. She’s at a great age for it, and my fiancée and I adore her. Unfortunately, my sister is upset that her 6-year-old daughter wasn’t invited. She says it’s unfair.”
The A, from Delia Cai at Slate: “Talk to your sister about whether there’s another form of reassurance or validation that you can offer her (either directly related to the wedding or not) to show how important your relationship is to you while you’re gearing up for this new chapter in life.”
The Overthinker adds: I remain totally baffled by this one. Did the columnist read this person’s letter!?
For starters, this isn’t a child-free wedding. The letter writer’s 8-year-old niece is attending as flower girl. Secondly, the sister in the headline isn’t “begging for an exception.” There is no real rule in the first place! Finally, and most disturbingly, the bride who wrote this letter seems to have at least two nieces, but only one (the flower girl) is called a “niece”; the other (the uninvited child) is referred to as her “sister’s daughter.” What is going on here!?
This is the kind of query where the advice-giver should be holding up a mirror to the letter writer. Yes, you have the power to ban all children but one from your wedding. Yes, you can single out a six-year-old child and make them feel excluded to the point of tears. And yes, you can totally choose to become the “family grinch,” as one commenter put it. But why, oh why, would you want to?
“My Mom Can’t Stand My Sister-in-Law. How Can I Stop Her Griping?”
The Q: The letter writer loves her sister-in-law; her mother doesn’t. “When I finally told my mother how much it hurts me to hear her say these things about my sister-in-law, she said that she needed to air her frustrations with someone.”
The A, from Lori Gottlieb at The New York Times: Set a boundary in three simple steps: 1) State the issue and your desire to come closer, 2) Set the boundary, and 3) Hold the boundary.
On this last point, Gottlieb emphasizes: “If you end the conversation only 90 percent of the time, then why would the other person honor your request when 10 percent of the time, you can’t honor it yourself?”
The Overthinker adds: You heard it here first, folks: In 2025, “boundaries” are OUT. “Limits” are IN.
What’s the difference?
Boundary-setting1 is a pop psychology trend with no single definition. In my experience, it typically refers to a hard and fast rule one individual sets for another’s behavior: “If you do X, I will do Y.” Or, “If you don’t do Z, I will do A.” In my life, I’ve found that boundaries often raise the stakes in situations that are already fraught; come with the conviction that boundaries “must” be observed 100% of the time by all parties; and leave little room for the nuanced reality of intimacy, interdependency, and compromise. In short, a boundary runs the risk of turning our human relationships into inflexible bureaucracies.
The idea of “observing limits” comes from dialectical behavior therapy (DBT). Instead of setting hard boundaries with clients, an individual therapist is encouraged to observe the things that got in the way of them being the best possible clinician.2 Instead of “setting” pre-defined “boundaries” derived from dubious received wisdom about how therapists and/or clients “should” behave, therapists had the opportunity to create more idiosyncratic limits that were actually effective for them. And while “boundaries” went stale, “limits” evolved with the situation. This could be both in the short term (“extending your limits” to help this client through this crisis) or in the long term (reducing your caseload to make more time for your growing family). Needless to say, 100% adherence to a limit is not what defines a limit’s legitimacy.
The truth is, it’s harder to observe limits than set boundaries. Limits respond to reality, while boundaries are based on our faulty mental forecasts about the future. Responding to reality is always more difficult than we give it credit for. Limits ask us to balance our relationships, our goals, and our self-respect, moment by moment. And, in the DBT framework, they ask us to do so non-judgmentally — that is, with an appreciation for the “why” of our own needs, and the needs of others. Perhaps most importantly, limits ask us to cultivate, communicate, and reexamine them over time. We observe. And we observe again.
While I have my qualms with Gottlieb’s set-up, I don’t know that my practical advice for this letter writer would be all that different than the script Gottlieb offered. I’d simply add is 1) make sure your limits are your own, and not the advice columnist’s, 2) validate that your mom does need someone to work through her feelings with and, at least for now, it can’t be you, and 3) consider adding that this is your limit right now. . . and you’ll observe how your feelings change as the situation evolves.
I really enjoyed this pop psychology history of “boundaries” from The Guardian, which traced the term back a 1989 self-help book by motivational speaker and self-described “interventionist” Jeff VanVonderen , who wrote: “Boundaries are those invisible barriers that tell others where they stop and where you begin. Personal boundaries notify others that you have the right to have your own opinion, feel your own feelings, and protect the privacy of your own physical being.” OK!
There’s a really funny example of Marsha Linehan, the creator of DBT, observing her own limits. She said to a client something along the lines of, “When you do X, it makes it harder for me to do therapy with you, so I really need you to stop doing X.” And the client said something like, “What if I don’t stop? Are you going to quit being my therapist?” Linehan responded: “No, I’ll keep being your therapist, I just won’t like enjoy it.”