Think about the last time a stranger made a lasting impression on you. Not through a dazzling compliment or a perfectly timed joke — but through a question. A question that made you pause, that invited you to talk about something you actually cared about, that signalled the other person was genuinely curious about who you are rather than what you look like.
That moment is rarer than it should be, particularly in online dating chat, where most conversations follow a script so familiar it has become almost invisible: Hi, how are you, what do you do, do you come here often. The format is not wrong exactly — it is just forgettable. And forgettable is the enemy in a space where the average person is carrying on three to seven conversations simultaneously and trying to work out who is actually worth getting excited about.
The good news is that standing out in online chat does not require a personality transplant or a screenwriting degree. It requires one thing done well: asking a question that invites a real answer.
Why Most Opening Questions Fail
The conventional opener — "How was your weekend?" or "What do you do for fun?" — is not bad in concept. In theory, it is an invitation to share something personal. In practice, it functions like a form field. Most people answer it with the same low-effort response they have given dozens of times before, and the conversation proceeds along well-worn grooves toward nowhere in particular.
The problem is not the topic. It is the framing. A question like "what do you do for fun?" puts the other person in a position of generating a list, which is inherently a bit dull to produce and even duller to read. "I like hiking, cooking, and travelling." Great. So do approximately forty million other people on dating apps. The question has technically been answered, but nothing memorable has been shared.
What makes a question memorable — what makes someone put their phone down and actually think before they answer — is specificity and genuine curiosity. Specificity because vague questions invite vague answers, and genuine curiosity because people can sense, even through text, whether a question is being asked by someone who wants to know the answer or someone who is just following a script.
The Question That Changes Everything
The question that does the most work in early online chat is some version of this:
"What is something you are quietly really proud of that most people who meet you would never guess?"
Or, depending on the conversation's tone, variants like:
- "What is one thing you care about that would completely surprise someone who just looked at your profile?"
- "What is a skill or interest you have that feels like a secret identity compared to what you do for work?"
- "What is the thing you most enjoy talking about when someone actually asks?"
The exact wording matters less than the structure. What all these questions share is that they:
- Signal that you are interested in the person beneath the surface presentation
- Give the other person permission to share something they genuinely care about rather than something they think they are supposed to say
- Invite a response that is inherently unique — nobody has a canned answer ready for this
- Create an immediate sense of being seen, which is one of the most powerful feelings a conversation can produce
The Psychology Behind It
There is a body of research, most famously associated with the psychologist Arthur Aron, suggesting that interpersonal closeness can be generated surprisingly quickly through a particular kind of question-and-answer exchange — one where both parties progressively share things that feel personally meaningful rather than socially safe.
Aron's best-known work involved pairs of strangers who were guided through 36 increasingly personal questions and then asked to spend four minutes making sustained eye contact. The results, including a reported real-life marriage between two participants, went viral in a 2015 New York Times essay. But the underlying finding is more nuanced and more useful than the viral story suggests: it is not the specific questions that create closeness, and it is not the eye contact. It is the experience of mutual vulnerability — of both people revealing something real rather than performing something acceptable.
You cannot replicate this in full with an online dating opener. But you can start the process. A question that invites the other person to share something they are quietly proud of does exactly that — it creates a tiny, low-stakes moment of authentic self-disclosure, and it signals that you are the kind of person who is capable of receiving it. That signal, more than anything else, is what makes someone memorable.
Why This Works Even Better Online
In face-to-face conversation, signals of genuine interest are communicated through body language, tone of voice, and sustained eye contact. Online, you have only words. This means that the quality of your questions carries more weight, not less, than it would in person.
When someone receives a question that is clearly tailored, clearly curious, and clearly different from the template questions they have been fielding all week, it does something important: it makes your conversation feel distinct. Instead of being one thread among many that feels interchangeable, it becomes the one they actually look forward to opening.
This is not a small thing. Platforms like iwillfindyou.love, which put no paywall on messaging so you can have real conversations from the start, are full of people who are genuinely trying to connect — and genuinely struggling to make their conversations feel different from everyone else's. The people who stand out are almost never the ones with the wittiest openers or the most polished profiles. They are the ones who make the other person feel interesting.
Making someone feel interesting is primarily achieved through the quality of your questions.
How to Use It Without Sounding Like a Quiz Show
The most common mistake when people discover this approach is to deploy it too abruptly or too mechanically. Dropping "tell me something about yourself that would surprise people" as a cold opener, before any warmth has been established, can land as odd or even slightly confrontational.
The better approach is to let a question like this arise naturally from the conversation's existing texture. If someone mentions their job, that is an invitation: "What is it about that work that most people who haven't done it would completely misunderstand?" If they mention a hobby in their profile, try: "I saw you're into [thing] — is there a part of it that you're secretly more obsessed with than the usual version most people know about?"
These are essentially the same question as the headline version, but they are grounded in something specific about this particular person, which makes them feel even more tailored — and therefore even more memorable.
The other key is to answer your own question, or at least to be ready to. The moment someone responds to a question about what they are quietly proud of, you have created an implicit social contract: they have been vulnerable with you, and you now owe them a corresponding willingness to share. The conversations that go somewhere are almost always exchanges, not interviews.
What Happens Next
When this approach works — and it works consistently enough to be worth making a habit — the conversation changes character almost immediately. Instead of a mutual exchange of résumé points, you are suddenly talking about what actually matters to both of you. Instead of trying to establish whether you are superficially compatible, you are getting glimpses of who this person really is.
That is useful information in its own right. It is also significantly more enjoyable than the alternative, and it tends to produce something that most online dating conversations conspicuously lack: a shared sense of having actually connected.
From Chat to Meeting
There is a secondary benefit to this approach that is worth naming: conversations that get real faster also tend to progress to actual meetings faster.
One of the consistent frustrations in online dating is the large number of conversations that run for days or weeks and then simply fade without ever becoming anything. This happens for a lot of reasons, but one of them is that conversations that stay at the surface level — swapping generic facts about each other's lives without ever getting to anything that actually matters — tend to plateau. There is nothing pulling either person forward. No momentum, no sense of discovery, no feeling of wanting to know more.
A conversation that establishes early on that there is something real to discover has a very different energy. It creates investment. And investment is what makes someone motivated to suggest a meeting, and to follow through on it.
The question is simple. The effect is not.
A Note on Authenticity
None of this works if the curiosity is performed rather than genuine. People can tell, even in text, when a question is a technique rather than an expression of actual interest. The version of this that works is the one where you ask because you actually want to know — because you are genuinely curious about what is going on inside the person on the other side of the screen.
If you are not particularly curious about the people you are talking to, that is worth examining before you look for conversational strategies. The question is a tool for expressing genuine interest, not a substitute for it.
But if you are the kind of person who is genuinely interested in people — who finds other human beings actually fascinating rather than just theoretically interesting — then this approach is simply a way of communicating that more clearly. And in a space as noisy and fast-moving as online dating chat, communicating it clearly is most of the work.
Further Reading
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Arthur Aron, Edward Melinat, Elaine N. Aron, Robert Darrin Vallone, and Renee J. Bator. "The Experimental Generation of Interpersonal Closeness: A Procedure and Some Preliminary Findings." Personality and Social Psychology Bulletin 23, no. 4 (1997). The original study behind the "36 Questions" phenomenon — foundational reading on how vulnerability and mutual disclosure accelerate interpersonal closeness.
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Charles Duhigg. Supercommunicators: How to Unlock the Secret Language of Connection. Random House, 2024. A recent, research-grounded look at what distinguishes people who communicate exceptionally well — with particular attention to how the right questions shift the register of a conversation.
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Celeste Headlee. We Need to Talk: How to Have Conversations That Matter. Harper Wave, 2017. Practical and warmly written guide to the art of genuine conversation, with useful coverage of how listening shapes what people choose to share.
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Sherry Turkle. Reclaiming Conversation: The Power of Talk in a Digital Age. Penguin Press, 2015. A thoughtful examination of what is lost and what can be preserved in digitally mediated communication — particularly relevant for understanding why quality questions matter more online than in person.
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Mandy Len Catron. "To Fall in Love with Anyone, Do This." The New York Times, January 9, 2015. The essay that brought Aron's 36-questions research to mainstream attention — readable, personal, and a good entry point into the literature on closeness-generating conversation.