Questions to Ask Crush the Turtle
Playful get-to-know-you questions for a crush: light enough to send over text, specific enough to lead somewhere. They start on easy ground and move towards the things people usually only say once they are comfortable.
The questions
Open any question for the note
What did you actually do with your weekend, not the polite version?
Why ask it
The polite version is a summary; the real version has a bad film, a nap and an argument with a flatmate in it. Asking for the second one signals early that you are not looking for a performance, and it usually gets you the first genuinely funny thing they say.
What are you into at the moment that you could talk about for an hour?
Why ask it
This gives permission to be enthusiastic about something niche, which is where most people are at their most likeable. If they cannot name anything, notice it without judging: some people are between interests, and some are guarded with someone new.
What is your order at the place you go to most?
Why ask it
Small and easy to answer, and it hands you a specific detail you can use later, which matters more at this stage than anything profound. It also quietly tells you where they spend their time and whether they are a creature of habit.
Are you a plan-it-out person or a decide-at-the-door person?
Why ask it
The answer is practical information rather than trivia, because it tells you how to ask them to do something without it feeling like pressure. People are usually accurate about this, and they often volunteer what happened the last time they tried being the other way.
What is something you liked when you were fifteen that you still like now?
Why ask it
Long-standing enthusiasms come with more warmth than current ones, and there is usually a slightly embarrassed laugh attached. It also gets you past the version of their taste that they curate for new people.
What was the last thing that made you laugh so much you had to stop what you were doing?
Why ask it
Asking for one incident rather than for their sense of humour in general produces a story instead of a category. Notice whether the story involves a friend, a video or something at work, because that tells you where the good parts of their week happen.
Who did you tell first, the last time something good happened?
Why ask it
This maps who is closest to them without asking about their relationships directly. A parent, a sibling, one particular friend or nobody at all are four quite different answers, and the last one is worth sitting with rather than rushing past.
Where would you take someone who had never been to your city?
Why ask it
It gets an itinerary out of them, which doubles as a list of things they actually like doing. If everything on the list is a tourist stop rather than somewhere they go themselves, they are probably still being careful with you.
What do people tend to get wrong about you at first?
Why ask it
Almost everyone has a ready answer, and it shows you the gap between how they land and how they see themselves. Quiet mistaken for cold and loud mistaken for confident are the two common ones, and the correction is usually the more honest self-description.
What are you better at than you let on?
Why ask it
Framed this way it invites a small brag without the awkwardness of asking what they are proud of. The answers tend to be oddly specific skills, and asking where they learned it is where the conversation gets good.
What is the nicest thing someone has done for you that you did not ask for?
Why ask it
This reveals what registers as care to them, which is more useful than knowing their favourite film. Someone who describes a practical favour and someone who describes being remembered are telling you different things about what they will want later.
What did you get obsessed with and then drop completely?
Why ask it
Abandoned hobbies are funnier and less defended than current ones. They also answer honestly whether this is a person who finishes things, which they will admit here far more readily than if you asked directly.
How do you like to spend a day when nothing is planned?
Why ask it
This is the compatibility question hiding inside a light one, because empty days show whether someone recharges alone or in company. Listen for whether their ideal version of the day includes other people at all.
What is a small thing that ruins your day more than it should?
Why ask it
Inviting a minor complaint gives them a safe way to be unguarded, and the specificity usually comes across as charming rather than sour. If the answer turns out to be a large thing rather than a small one, take that as a signal about what they are carrying.
What were you like at school?
Why ask it
Short question, long answer, and it fills in family, place and how other people treated them without your having to ask about any of that. A very short answer here often means it was not a good time, so let them steer from there.
Which of your friends knows the worst about you?
Why ask it
Warmer than it sounds, because the answer is a person they trust rather than a confession. If they name someone from fifteen years ago, that tells you how they hold onto people, and if they cannot name anyone, that is worth knowing too.
Is there something you have changed your mind about recently?
Why ask it
This shows whether they can hold a position loosely, which predicts how disagreements will go better than anything they say about communication. Small subjects count, and a complete blank is informative in its own way.
What is the trip you keep meaning to take and never do?
Why ask it
Better than asking where they would go with unlimited money, because the reason it has not happened is the interesting part: cost, time, nobody to go with, or a person they would once have gone with. Follow the reason rather than the destination.
What do you want more of in the next year?
Why ask it
Open enough that they can answer lightly or seriously, and where they take it shows how much they trust the conversation. Concrete answers about a place, a job or a person mean they are letting you further in than an answer about wanting to be happier.
What is something you would rather someone knew about you early than late?
Why ask it
Kept for last, this is an invitation rather than a demand, and it lets someone name a circumstance, a boundary or a habit on their own terms. A deflection is a perfectly good answer and should be treated as one rather than pushed.
How to use these questions
Practical guidance for the conversation itself
Making it a conversation, not a quiz
Two or three per conversation, not twenty
Working down a list in order starts to feel like an interview, which kills the thing you are trying to build. Pick a couple, follow whatever they open up, and keep the rest for another time.
Answer everything you ask
The exchange only works if it is mutual. Give your own answer at roughly the same length as theirs, and go first if the question is at all revealing.
Follow the detail, not the topic
If someone mentions a specific person, place or moment in passing, that is the thread. Asking who was there or what happened next moves things forward better than reaching for a new question.
Over text, ask one thing at a time
Stacked questions in a single message get one answer, usually to the last one. Send one, wait, and respond to what they actually said before adding anything else.
What the answers tend to tell you
- Length is the signal, not content. Whichever question got the longest answer is the subject to stay on.
- Whether they ask it back. People who are interested return questions, usually within a message or two.
- How they talk about the people in their stories. Warmth towards friends and family predicts more than anything they say about relationships.
- Where they go vague. A short, smooth answer to an otherwise interesting question is usually a boundary, and it deserves the same respect as a stated one.
- Whether answers get more specific over time. Growing detail across a few conversations is the clearest sign this is going somewhere.
What to avoid
Do not open with the heavy ones
Questions about family, past relationships or what they want from life are fine later and strange early. Starting there tends to make people polite rather than open.
Do not treat a short answer as a challenge
If you get two words, change the subject rather than rephrasing and asking again. Pushing turns a light conversation into an uncomfortable one very quickly.
Do not audit their history
Exes, numbers and why past relationships ended are not get-to-know-you material, whatever the framing. Those conversations happen when someone chooses to have them.
Do not perform your answers
A rehearsed, impressive reply to a light question is more off-putting than a boring true one. The advantage of these questions is that ordinary honest answers work better than clever ones.
Follow-ups worth having ready
- "How did that start?" Works on almost any interest or habit and usually produces a story.
- "Who was with you?" Turns an account of an event into an account of their life.
- "What would you do differently?" Good for anything they mention regretting, without making it a serious conversation.
- "Is that still true?" Useful when someone describes an old version of themselves, and it often gets the most thoughtful answer of the evening.