I’m going to be upfront with you before we get into this one.
This episode made me uncomfortable. And I almost didn’t record it.
Not because the conversation wasn’t good. Not because the guest wasn’t thoughtful. But because I knew the second I hit publish, some of you were going to have a strong reaction. And I want to honor that reaction, whatever it is, before we go any further.
Here’s what I also know: people are already using AI to navigate their friendships. Right now. Whether you think that’s a good idea or not, it’s happening. And most of the people doing it are doing it in the least useful way possible: typing two sentences into a chat window and asking a stranger with zero context what they should do.
That’s not what today’s episode is about.
Today I’m talking with Connor Joyce, a Senior User Researcher on the Microsoft Copilot team who has spent over five years working in AI and applied behavioral science. Connor has built something he calls Project Folders: detailed, context-rich containers about his core relationships that he uses as a tool for self-awareness, pattern recognition, and showing up more intentionally with the people he cares about.
Some of you are going to love this. Some of you are going to hate it. Some of you are going to land in the messy middle with me.
All of those responses are valid. That’s actually the point.
Why Most People Are Using AI for Relationships Wrong
Before we get into what Connor is doing, let’s talk about what most people are doing. Because Connor said something that I keep coming back to.
When you go into ChatGPT and type “I’m fighting with my friend, she did this thing, why do I feel so bad?” you are asking a stranger with no context for advice. And the system is going to give you an answer. It’s going to sound coherent. It might even feel like it resonates a little.
But here’s the thing Connor explained that I think most people don’t fully understand about these systems:
“It’s kind of like a horoscope sounds coherent because it’s written in a way that fits… pretty much no matter what you’re feeling, something in there is going to resonate. That’s how these systems, without strong context, will do.”
Without context, you’re getting the collective knowledge of the internet filtered through a system that is, by design, trying to keep you engaged. These systems have become, as Connor put it, “very sycophantic.” They want to tell you what you want to hear. And that is genuinely not useful when what you actually need is someone to help you see the thing you’re missing.
The thing you’re not even thinking to look for. The unknown unknown.
That’s the whole problem with the way most people are starting these conversations. And it’s also exactly where Connor’s approach flips the script.
What a Project Folder Actually Is
Here’s the simplest way I can explain it, because when Connor first described this, I needed a minute to translate it into something I could actually picture.
Imagine you’ve been keeping a journal for years. Every time a friend told you something important about themselves, you wrote it down. Every time you noticed a pattern in how you show up in a relationship, you wrote it down. You have therapy session summaries in there. Notes from coaching. Reflections on past relationships. A full timeline of a relationship that ended. Artifacts from grief counseling. Dozens of documents, all about you, your history, your patterns, your values.
Now imagine you walk into a therapist’s office and hand them that entire journal before your first session. And then every time you come back, they’ve read all of it, they’ve reviewed all their previous session notes, and they’ve had an intern writing summary reports on the patterns they’re seeing across everything.
That’s a Project Folder.
Connor has these for his core relationships. He has one for a close friend he’s been coaching through a major life decision. He has one for a friendship that went through a significant conflict. And he has one for the relationship he’s in right now, which he’s been using to work on his anxious attachment style in real time.
“They become these persistent containers of context that I can go in and ask specific questions to… and it is capturing themes that I myself haven’t even begun to understand, because it has access to that collective knowledge of humanity.”
(I know. There’s a lot to sit with there. Stay with me.)
But Wait — Do His Friends Know?
I asked this. You were going to ask this. Let’s just address it.
Yes. All of the people Connor has folders for know about them. It didn’t always start that way. It was more that when an insight from a folder came up naturally in a conversation, he’d mention it. “I actually have this folder in ChatGPT that I use for my own personal growth, and I used it to understand this situation better.”
He was honest with me that he doesn’t ask permission before creating one, which is something he said he’d have to reflect on more. His framing was that he doesn’t ask permission to talk about someone in therapy either. Fair point. Also a genuinely interesting question worth sitting with.
And then he said something that I haven’t been able to stop thinking about:
“I literally have never asked myself that question until you just said that. And then I was like, I wonder if people do about me.”
Which means… yeah. Someone could have a folder about you right now. We don’t know. And that’s a real, new reality we’re all going to have to figure out how we feel about.
Listen to the full episode at friendshipirl.com/episode169 for the complete conversation, including Connor’s honest reflection on this question and why he lands where he does on the ethics of it.
The Part That Actually Stopped Me
Here’s where this conversation shifted for me.
Connor was describing a situation where something happened in his romantic relationship that genuinely hurt him. Every person he told the story to said the same thing: that person hurt you. Full stop.
But when he went to his folder, framed correctly, he got something different. The system didn’t tell him that person hurt him. It told him that person did something, and he was hurt by it. And that distinction, that small, precise reframe, opened up something that years of therapy hadn’t caught.
“In friendships and in relationships, sometimes people are going to do things that ultimately create hurt. But that doesn’t mean that person hurt you. And it means that, at least in my moral framework, I have to own that hurt.”
The framing of the question was everything. He didn’t ask “why did she hurt me?” He asked “why would that person take this action that led me to feeling hurt?” One question keeps you stuck. The other one opens a door.
And that’s the whole point of how Connor uses these tools. Not to get validation. Not to feel good. To find the unknown unknowns. The things you’re not even thinking to look for.
Values Alignment: The Framework Underneath All of It
One of the most interesting things Connor described is how he’s trained his folders to run every situation through his core values before giving him any kind of response.
He did something called values alignment therapy, where he spent months revisiting his biggest regrets, his biggest accomplishments, and what was underneath both. He came out of it with four values: growth, accountability, transparency, and financial stability.
Now, when he brings a situation to a folder, it doesn’t just give him advice. It checks the advice against those four values, one by one. It might flag that a certain choice aligns strongly with growth but shows a caution symbol next to transparency. It gives him four options on a spectrum from complete self-protection to full vulnerability, and tells him which values each option serves.
The result? Less regret.
“I was carrying around a lot of regret and shame, and I realized the core of it was decisions that were made based on emotions… letting other external factors make decisions for me. I’ve learned now with those values that if all four options align with my values and I take any of the four, no matter the outcome, I might be sad, I might be disappointed, I might be hurt, but I won’t be filled with shame. Because I can at least say I did the best with who I actually want to be.”
I want to be honest: I’ve never done values alignment therapy. And after talking to Connor, I’ve been sitting with the question of what MY core values actually are. It’s harder than it sounds. I don’t have a clean answer yet.
But here’s what I do think: if you’re someone who constantly second-guesses yourself after interactions with friends, if you leave conversations feeling like you messed up or said the wrong thing, maybe getting clear on your values could help. Even without the AI piece. Because if you know what matters to you, really know it, then at least you can trust that you stayed true to yourself, even when things didn’t go the way you hoped.
This feels like a bigger topic that deserves its own episode, and I’m already planning it. So stay tuned for that.
How to Actually Start (If You Want To)
Connor was clear about what NOT to do: don’t just open ChatGPT, type two sentences about a fight you’re having, and ask it what to do. You’re going to get a horoscope. It’ll feel vaguely relevant. It won’t actually help.
Here’s what he suggests instead:
- ▪️ Start with a specific goal, not a specific person. Ask yourself: within all of my relationships, what is the ONE thing I most want to work on right now? Maybe it’s a pattern you keep repeating. Maybe it’s a conflict you don’t fully understand. Maybe it’s an attachment style you’re trying to shift. That’s your seed.
- ▪️ Build the context before you ask the questions. Any artifacts you already have: journal entries, therapy summaries, notes from coaching, old text threads, anything that gives the system a real picture of you and this relationship. Feed it all in.
- ▪️ Ask questions that invite more questions. Not “what should I do?” but “why might I be feeling this?” Not “was I right?” but “does this align with my values?” The goal is to surface what you’re NOT thinking about, not to get permission for what you’ve already decided.
- ▪️ Use it as a launch pad, not a landing pad. Connor was clear about this: the insights are meant to help you take real action in real life. Not to live in the chat. The tool is useful only if it gets you somewhere with an actual human being.
And one important caveat from Connor: these systems can hallucinate. They can sound completely confident and be completely wrong. For anything significant, run the insight by a real person, a friend, a therapist, someone, before you act on it.
What I Actually Think About All of This
Here’s where I landed after sitting with this conversation for a couple of weeks.
Connor isn’t using AI to replace his relationships. He’s using it to show up better IN them. To understand his own patterns. To break cycles that weren’t serving him. To make decisions he can live with.
Strip away the technology and that’s just… good relationship work. It’s the same work we talk about every week on this podcast. The tool is new. The work isn’t.
Do I think everyone should go build Project Folders about their friends? No. Do I think this will work for everyone? Also no. But do I think we need to stay open to the reality that people will use AI in ways we haven’t imagined yet, including in their closest relationships? Yeah. I do.
Because my real concern, the thing that keeps me up at night about friendship in 2026, isn’t AI. It’s that we’ve created a culture where people feel so much pressure to get their relationships RIGHT that they’re paralyzed. They spiral about every text. They overthink every interaction. They isolate because they don’t know what to do.
If AI, used thoughtfully and intentionally, helps someone break through that paralysis and actually connect with another human being? I’m not going to stand in the way of that.
If this conversation sparked something for you, listen to the full episode at friendshipirl.com/episode169. Connor also wrote a practical guide to getting started with this approach, and I’m linking it in the show notes.
Resources Mentioned
- ▪️ Connor Joyce on LinkedIn
- ▪️ Starter guide for building relationship Project Folders for your Friendships and Relationships
