Good Faith, Bad Strategy?
In work, you chase. In life, less so.
She messaged me at 7:42 pm on a dating app.
Six words. One emoji. The photos looked real but not quite right for here—this place, this year. Somehow too crisp and yet, too pixelated, like an image downloaded and retouched over and over. The message itself felt personal, specific enough to dismiss the idea of a chatbot. And yet, something in it smelled of “too good to be true.”
The kind of message that would make you feel warm if it were real.
By 9:15 pm, I was deep in the kind of quiet vetting most investigators would call “due diligence” and most friends would call “strange and unnecessary.” There wasn’t much. An Instagram that seemed almost right but was private, and had no last name. Nothing on Facebook, no seemingly mutual connections. Still, her prompts were funny. Her photos were plausible. She had nice hands and a dog. The mystery was flattering.
I wasn’t suspicious, exactly. I was curious. And fine, I wanted to verify her authenticity. And in the process, appease the competing parts of me. The part that blurs “personal boundaries” and “professional rules” until I can’t remember where my rules apply, exactly.
In a proper investigation, you put true energy into checking assumptions. You confront and challenge your biases, you intentionally clear your mind of useless preconceived notions.
But in a personal investigation? Flip and reverse. You rely on instinct. You work the gut. You read tone. You chase anomalies, and when you’re trained to recognize those anomalies, everything can start to feel just a touch skeptical.
In real casework, a clearly edited photo, a slip in a story, even a simple odd silence is enough to dig your heels in. You chase it. And that reflex doesn’t go quietly dormant after 5 pm.
I’m good at pulling threads. So, I took this innocuous dating app message, and I started pulling. And pulling. Until I realized the thread wasn’t attached to much of anything at all, and I was wasting more of my own time than this probably-not-so-real person was.
While most of us lose our good nature in dating after 30, there is this quiet cultural script that asks you to “assume good intent.” In many ways, I don’t disagree. It sounds noble. It sounds mature. And it is, in theory, how we create space for curiosity, for awkwardness, for growth and potential.
But online? In a context where people can disappear without consequence, perform sincerity with three messages written by ChatGPT, delete their identities in a swipe, or create entirely fake profiles and personalities? Assuming good faith is not always generosity. Sometimes, it’s poor threat modelling.
I don’t work in romance scams. But I’m not unfamiliar with them. I have an incessant curiosity about the humanity of it all—the vulnerability and hope that allows us to interact with idealism that we know, on some level, can’t possibly be real.
If someone wants to be seen, they make it possible. Maybe not immediately. Maybe not loudly. But they will give you something to hold. The name of a neighbourhood, a local coffee shop they enjoy. A photo in a place you’ve been. A phone number connected to an actual provider and a SIM card. A story that checks out. An account that’s not three months old with no tagged photos.
The woman I was messaging never lied to me. She just never told me anything true. She offered intrigue instead of intimacy. Her stories came in half-explanations, delivered like riddles. “That’s a whole bottle-of-wine conversation.” “I could tell you, but I don’t want to ruin the suspense.”
She said she wasn’t seeing anyone else but was too busy preparing for a conference—a conference that would take her out of the city for over a week—to meet in person. Said she deleted Instagram for “mental health reasons” and because it “no longer aligned with her values.” And somewhere in my brain, a familiar narrative lit up: Maybe she’s not out. Maybe she’s afraid.
Maybe, maybe, maybe.
I could build an entire person out of “maybe,” an entire psychology out of vague gestures. And I was doing it in good faith—to believe this was a sympathetic person going through sympathetic things.
That was the problem.
Here’s what good faith can get you online:
Breadcrumbs.
Mixed signals.
People who answer your direct questions with delayed, confusing responses and are frustrated when you ask again.
Weeks of guessing what their real circumstances are, if this is their true identity, why they seem both available and unable to follow through.
Here’s what unearned good faith won’t get you:
The truth.
A meaningful connection.
A better outcome.
Your time back.
When I directly asked this woman if she was genuine, the response was similarly tricky—not yes, not no. When I asked if she truly wanted to meet, she said yes but couldn't choose an actual date. When I asked if the photos were really her, the account disappeared on my end.
The trickiest people are not just the ones who outright lie. It’s the ones who give you enough potential truth to keep you in the dialogue, guessing, justifying. Sometimes it’s deliberate, sometimes it’s just immaturity. But either way: it costs you.
You become the one doing the interpretive labour. You’re no longer relating, you’re managing evidence, filing it away.
So here’s what I do instead: I do not assume good faith. I also do not assume bad faith or deception. I look for clear evidence of intent. I ask questions early. I watch for clarity, coherence and reciprocity. I ask myself not just how does this feel but what is it asking of me?
In an investigation, if someone disappears, you exhaust every resource and every angle to find them. You build out timelines. You dig for data, and call people who have nearly forgotten that name. You double down until you get your answer—because answers matter.
But here? As a person simply seeking connection, if someone doesn’t want to be found, the story has ended.
You’re not tracking a mark. You’re not saving anyone. You’re looking for humans who meet you halfway. And if they won’t—if all they leave are broken links and smoke signals—you can let them vanish.
Curiosity is not the same as connection. And being “nice” is not the same as being honest. And sometimes, when people say “it’s complicated,” what they really mean is: we both know the true answer isn’t the one you’re looking for.