Why Does My Friend Argue About Everything?Dear Nina,I’m having a major issue with a close friend, “Ainsley,” who has been there for me for many years. We share several good friends and our kids attend schools in the same district. The kids aren’t in the same grades, but they’re close in age so on top of doing friend stuff together, Ainsley and I are also part of the same community. We talk on the phone consistently, text a lot, and do things together in person. Like I said, she’s a close friend! I like so many things about her. She’s thoughtful, always up for doing fun things together, and I know she’d drop everything if I really needed her. The one issue that has been building up over time is that she is the biggest contrarian. “Can I be the devil’s advocate?” is something she says often. Ainsley takes the other point of view no matter the topic. It’s a combo of being a contrarian + a know-it-all. If we were debating something like politics it would make more sense as people have different points of view they might want to represent. But I’m referring to the most unremarkable details of life. I could be telling Ainsley about an issue with my kid and what she’s dealing with in fifth grade, and she will have an answer for everything. Why didn’t I try this or that? Why don’t I consider x, y, z? Okay, maybe that’s one issue worthy of discussing so not a great example. If I liked a book, Ainsley thought it wasn’t worth finishing. If I didn’t finish a book she recommended, she’s really surprised I didn’t enjoy it. That’s another thing. She’s often “surprised” by my choices and opinions even though they’re pretty run-of-mill choices and opinions. Again, we’re talking about tiny things here. I realize how petty this sounds as I’m writing it, but that’s how it feels on the receiving end to get commentary about anything and everything I say. I’m constantly having to defend my take on any little thing—which grocery store I like, what time I eat dinner, and on and on and on. Ainsley always knows better. I assume you’re thinking, “So stop spending so much time with her.” It’s not so easy. Our lives are very intertwined. Also, any time I think about distancing myself from this friendship, I remember all the times she’s been a great friend. I can’t figure out if she’s getting worse or I’m getting less tolerant about this trait of hers as I get older. I guess what I’m asking is, how do I get Ainsley to stop putting me on the defense about so many topics? Or is that impossible and I should consider distancing myself since I know we can’t really change another person? Thanks, tired of being questioned and criticized... Continue reading this post for free in the Substack app
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Sunday, 14 September 2025
My Friend Is Always “The Devil’s Advocate”
Friday, 12 September 2025
⏳ Last Chance to Own the Madness—Sale Ends in 10 Days
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Wednesday, 3 September 2025
Stop Listening to Your Bully Brain: September Challenge
Stop Listening to Your Bully Brain: September ChallengeHow to quiet self-doubt, flip the script, and take small actions toward stronger friendships.
Every month on Dear Nina (the podcast) I offer a small challenge to deepen/revive the friendships already in our lives OR to make new friends. I say “our” because I do the challenges too. You can see the January - August challenges here. September’s challenge is unlike the others because it’s pushing for a thought-pattern change at least once this month. Most of the challenges focus on an action like planning a night out, starting a new friendship ritual, pursuing a hyper-local friendship, or changing where you spend time with friends. (All previous monthly assignments!) For September: Listen to your “bestie brain”This month’s Dear Nina Friendship Challenge taps into the fresh-start energy of September to help you quiet the “inner bully” telling you you're awkward or not desired. For the next few weeks, I want you to dial up your “inner bestie.” This idea came from Leslie Randolph, certified coach and TEDx speaker, who helps adults, tweens, and teens cultivate self-confidence that sticks. Leslie joined me for episode 162 of Dear Nina. We broke down self-confidence as a skill. We encouraged listeners to take courageous friendship steps even with fear present. And we discussed practical ways to reframe the stories you tell yourself so you can make and keep adult friendships at any stage of life. Here is the September assignment (or do it any month you’re reading this!)
Other highlights of episode 162 to help you:
Let me know how it goes!REMINDER: You can start the 2025 challenge any time. Each month is meant to stand alone and you don’t need an entire month to accomplish any of them. Come back and let me know how it went no matter when you try that month’s “assignment.”
Two anonymous questions you might have missed
Let’s connect outside of this newsletter: You can find me most often in the Facebook group, Dear Nina: The Group. All the social media links are below. I know I need to get rid of some them! Instagram | TikTok | YouTube | LinkedIn | My Website You’re a free subscriber to Dear Nina: Conversations About Friendship. Frustrated with some of your friends? You’re not alone! The anonymous letters are a perk for paying subscribers. You probably have a similar question. Upgrade any time for the full archive.
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