What Your WhatsApp Chats Reveal About Your Relationships (And How to Decode Them with AI)

06/03/2025

What Your WhatsApp Chats Reveal About Your Relationships (And How to Decode Them with AI)

Trigger Warning:

This is more powerful than you might expect. AI doesn’t just analyse words—it detects patterns in how you communicate. Be prepared for insights that could be fascinating, reassuring, or even a little uncomfortable.

The Digital Mirror In Your Pocket

If someone scrolled through your WhatsApp messages with your best friend, your partner, or your closest colleague—what would they learn about your relationship?

Would they see deep, meaningful conversations? Quickfire banter? Endless discussions about what to have for dinner? Or would they notice something you hadn’t—one person always initiating, another dodging difficult topics, or a tendency to over-apologise?

We spend hours a week communicating digitally, yet we rarely stop to analyse what those conversations reveal about the connections we value most. But what if AI could do it for us?

Last week, we ran an experiment. We took one of our longest-running message threads (four years to be precise), uploaded it to a GPT-powered AI, and asked a simple question:

“Based on our conversations, what can you tell me about our relationship?”

What came back was equal parts mindblowing and uncomfortable. Strengths we hadn’t articulated. Patterns we hadn’t spotted. And challenges we might have preferred to ignore.

So, naturally, we took it further.

This article is an invitation for you to try the same. With just a few simple steps, you can use AI to analyse your own digital relationships—uncovering insights that could make your connections even stronger.

Here’s how.

 

Step 1: Gathering Your Digital Conversation History

Before we let AI loose on your relationship dynamics, we need some raw material to work with. Your digital conversations hold an incredible amount of insight—but only if we extract them properly.

Who to Choose?

Pick someone you communicate with frequently and over a long period. Ideally, this should be a person you have a meaningful connection with—someone whose interactions you’d genuinely like to understand better. Some good options:
✅ A best friend you’ve known for years
✅ A partner or spouse
✅ A close colleague you collaborate with daily
✅ A family member you message regularly

Who not to choose? Probably not your Uber driver, your hairdresser, or that group chat that only exists to coordinate birthdays.

How to Download Your Chat History

Different messaging platforms have different ways of exporting messages. The key here is to save only the text—no images, GIFs, voice notes, or memes (as insightful as that sticker collection might be).

Here’s how to do it for WhatsApp:
1️⃣ Open the chat.
2️⃣ Tap the three dots (Android) or the name at the top (iPhone).
3️⃣ Select Export Chat and choose Without Media.
4️⃣ Save it as a .txt or .pdf file.

For iMessage, Telegram, or Messenger, there are similar methods (a quick Google search will get you there).

Privacy & Ethical Considerations

This experiment is for your eyes only. It’s about reflecting on your communication, not spying on someone else. If you’re analysing a chat with a close friend or partner, it might even be worth telling them what you’re doing—because who knows, they might want to try it too.  We did this collaboratively, as a pair.

 

Step 2: Running the AI Analysis

Now that you have your conversation history saved, it’s time to let AI work its magic. This is where things get really interesting.

Uploading Your Chat to AI

Most AI tools—such as ChatGPT, Claude, or Gemini—allow you to upload or paste text. If you’re using ChatGPT (which we did), here’s how:

1️⃣ Open ChatGPT (or your AI tool of choice).
2️⃣ If it has an upload function, simply attach your .txt or .pdf file.
3️⃣ If not, copy and paste a chunk of the conversation (depending on the word limit of the AI you’re using).
4️⃣ Once uploaded, you’re ready to ask your first big question.

The First Prompt: Relationship Strengths & Challenges

This is where the AI starts reading between the lines. Copy and paste the following prompt:

💬 “Based on our communications, what can you tell me about my relationship with this person? Identify the top five strengths of this relationship and the top five challenges.”

Give the AI a moment, and then… boom. You’ll get an analysis that may surprise you.

What to Expect from the AI’s Response

The AI will look for patterns—who leads conversations, how frequently you message, your tone, emotional nuance, and even power dynamics. Some things it might pick up on:
✅ A sense of humour that runs through your chats
✅ Emotional support and encouragement
✅ Unspoken tensions or recurring disagreements
✅ A communication imbalance (one person always initiating, for example)

At this stage, it’s likely there are a few Aha moments… But we once we’d started, we couldn’t stop, so here goes…

 

Step 3: Digging Deeper into Hidden Relationship Patterns

So, you’ve seen the AI’s take on your relationship’s strengths and challenges. Some parts may have felt spot on, others surprising, and a few possibly a little uncomfortable.

Now, let’s push further.

The first analysis showed us what was obvious. The next step is to uncover what’s unspoken—the dynamics we might not even realise are playing out.

The Second Prompt: Unearthing the Hidden Challenges

Time to ask AI the tougher question. Copy and paste this prompt:

💬 “Now, tell me the top five challenges in this relationship that I might be unaware of—or that may be difficult to acknowledge.”

This is where things can get really interesting. AI is trained to pick up on subtle linguistic patterns that humans often miss—repeated apologies, hesitations, power imbalances, avoidance tactics, even shifts in tone over time.

What the AI Might Spot:

👀 Unspoken Frustrations – Recurring themes where one person subtly expresses irritation (but the other never directly acknowledges it).

👀 Avoidance Loops – Are certain topics always deflected or ignored? Do tough conversations get cut short?

👀 Emotional Weight Distribution – Does one person always do the emotional heavy lifting—offering support but rarely receiving it?

👀 Passive vs. Active Engagement – Does one person consistently respond with short, functional messages while the other carries the emotional tone of the conversation?

👀 Patterns of Power – Are decisions being made equally? Who changes the subject first? Who softens their language more?

 

At this point, you’ll probably have a few big insights swirling in your mind. But insight alone isn’t enough.

Now, it’s time to turn analysis into action.

 

Step 4: Strengthening Your Relationship with AI-Backed Suggestions

Now that you’ve uncovered the strengths, the obvious challenges, and the hidden dynamics in your relationship, it’s time for the most important step: 

 

Action.

 

Self-awareness is great, but if we don’t do anything with it, then this whole experiment is just an interesting parlour trick.

The Third Prompt: How to Improve Your Relationship

Time to ask AI for some constructive guidance. Copy and paste this prompt:

💬 “Based on what you’ve learned about this relationship, give me five ways I can nurture and strengthen it in a way that benefits both of us.”

This is where AI shifts from analysis to coaching mode, helping you turn insights into practical steps.

What the AI Might Suggest:

✅ Balance the Energy – If one person always initiates, try making a conscious effort to check in first.

✅ Address the Unspoken – If certain topics get avoided, consider whether they’re worth bringing up (or at least acknowledging that they exist).

✅ Adjust Communication Styles – If one of you sends long, expressive messages while the other replies in short bursts, try adapting to meet in the middle.

✅ Express Appreciation More Often – AI often picks up on a lack of direct affirmations—so a simple, “I really appreciate you” can go a long way.

✅ Create More Shared Moments – If your chats are mainly logistical, plan something together that doesn’t revolve around scheduling or problem-solving.

 

Step 5: When the AI Flags Something You Weren’t Expecting

For most people, this experiment will highlight subtle relationship dynamics—things like communication imbalances, recurring themes, or emotional habits that could be adjusted for a stronger connection. But what if the AI picks up on something deeper, something unsettling?

Sometimes, we don’t fully see the patterns in our relationships until they’re laid out in black and white. And while that can be helpful, it can also be confronting.

Recognising Unhealthy Patterns

If AI points out something that feels sinister—like controlling behaviour, manipulation, emotional neglect, or coercion—it’s important to take a step back and reflect.

Some red flags to watch for:
⚠️ One-sided communication – Are you always apologising? Always initiating? Walking on eggshells?
⚠️ Dismissive or undermining language – Does the other person frequently belittle your concerns or downplay your emotions?
⚠️ Patterns of control – Do they dictate when and how you can communicate? Do they use guilt, withdrawal, or passive-aggression to influence your behaviour?
⚠️ Emotional imbalance – Do you give constant support but receive very little in return?
⚠️ Isolation tactics – Does the AI highlight patterns where the person subtly discourages you from seeing other friends or speaking openly?

💡 If any of this resonates, you might want to seek external support. This could be talking to a trusted friend, therapist, or professional coach. If you’re in a situation that feels coercive or abusive, know that help is available.

When This Experiment Highlights Your Own Behaviour

Not all uncomfortable insights mean someone else is the problem. Sometimes, AI will flag patterns that suggest you might be struggling with boundaries, avoiding difficult conversations, or repeating unhealthy communication styles.

And that’s okay. Awareness is the first step towards change.

If you recognise areas where you might want to grow, this could be the perfect moment to dig deeper into your own emotional intelligence, communication style, and relational habits.

How Lead Happy Can Help

At Lead Happy, we know that self-awareness is the foundation of great leadership—not just in work, but in life and not just of others, but of ourselves. Our Personal Exploration Programme is designed to help you understand:
🔹 Why you communicate the way you do
🔹 What emotional habits shape your relationships
🔹 How to build stronger, more authentic connections (professionally and personally)

If this experiment has left you curious, reflective, or even a little shaken, our coaching can help you make sense of it.

💬 If you’d like to explore how we work, drop us a message—we’d love to chat.

Final Thought: AI as a Mirror, Not a Judge

This experiment isn’t about letting AI tell you whether a relationship is “good” or “bad.” It’s about noticing things you might have missed and deciding what—if anything—you want to do differently.

If all it does is make you more intentional about how you communicate, that’s a win.
If it helps you strengthen a great relationship, even better.
And if it nudges you to get support where you need it—then it’s done something truly valuable.

🚀 Would you be brave enough to try this? Let us know what you think. Email us your revelations here.

Interested in learning more about yourself and your behaviours?  Discover more about Personal Exploration and how it can support you.

Interested in a discovery session to see how we can help? Click here to book a meeting.

Further Reading:

Personal Exploration:  The Foundation of Brilliant Leadership

Unpacking Team Dynamics:  Turning Relationships Into Results

Exploring & Managing Emotional Intelligence