questions to ask your crush

The questions to skip when asking your crush, and why.

The pre-dating context is unforgiving of wrong-pace prompts. A question that would be fine in an established relationship can collapse a crush dynamic into “we are just friends” or “they read me wrong”. The dating-content industry treats every question as fair game; they are not.

The page below is organised by the stage at which the prompt is wrong, plus a small set of forever-skip prompts. It is opinionated. Disagree where you want; the editorial position is that pace matters more in pre-dating than anywhere else, and the wrong question at the wrong moment is more damaging than no question at all.

The first-thread skips

  • Generic openers. “hey”, “what's up”, “how are you”. They signal you have not been paying attention. The first message has to do the work; specificity is the discipline.
  • Their dating history. Asking about exes or past dating in the first thread reads as either insecure (you are calibrating against competition) or premature (the relationship has not earned the conversation).
  • Anything that requires effort to answer. “Tell me about yourself”, “what is your life story”, the open-ended autobiography prompts. Small, specific questions are easier to answer and more revealing.
  • Premature flirty escalation. Direct or charged prompts in the first ten messages, before the rhythm has earned them. The flirty-questions page covers this in detail; the lean-in section is explicitly not for the early thread.

The mid-thread skips

  • Pressure questions disguised as casual ones. “When can I see you”, “what are we doing this weekend”, “do you want to be exclusive”. The mid-thread is too early for these; they read as a demand for commitment when there is no relationship yet.
  • “Do you like me”. Forces a binary that the friendship-or-romance ambiguity does not deserve. Reading their interest covers calibration prompts that surface the same information without the ultimatum.
  • Vulnerability prompts before mutual interest is established. Depth before the relationship has earned it reads as pressure. Once mutual interest is clearly leaning in, the same prompts can read as care; pacing is everything.
  • Pickup-artist patterns. Prompts that frame the conversation as a test (“qualify you”), use neg-and-tease structures, or treat affection as something to be earned. The intent reads through. Skip.

The trying-to-be-deep skips

  • Therapist-asking-a-stranger prompts. “What is your trauma”, “what is your biggest fear”, “what are your attachment-style patterns”. These read as therapy, not curiosity; the relationship has not earned the disclosure.
  • Vulnerability extraction prompts. Anything that asks them to be more vulnerable than you are willing to be. Reciprocity is the discipline. If you would not answer it yourself, do not ask it.
  • Performance-of-depth prompts. The kind that invite a poetic answer rather than an honest one. Specificity beats abstraction; ask for the specific memory, not the general feeling.
  • Hypothetical-jealousy traps. “What would you do if your ex came back”, “would you ever date X type of person”. The question is structured to catch them in a wrong answer; skip.

The flirty-but-actually-creepy skips

  • Generic-with-implication prompts. The kind that imply something racy without saying anything specific. Specific is flirty; generic-with-implication reads as a line.
  • Questions about their body in the early thread. Skip until the relationship has earned them.
  • Anything that requires a yes to land. Flirty assumes the right to receive a no without it being a problem; if a prompt requires a yes, it is pressure, not flirtation.
  • Prompts that compare them to other people. The kind that ask “am I more attractive than X”. Different intent; skip.

The forever-skip questions

  • “What is your number”. The famous one. The honest answer earns nothing; the dishonest one is corrosive; the question itself is judging. Skip forever.
  • “Why are you single”. A question that frames their relationship status as a problem to explain. Different intent; skip.
  • “What is your type”. Either the answer matches you and they sound shallow, or it does not match you and you feel measured. No good direction.
  • “Do you find me attractive”. Demands a compliment. The kind of question that, if answered yes, you cannot believe, and if answered no, ends the conversation.
Where to read next
How to use these prompts
The technique notes for the prompts that did make the cut.
Reading their interest
The right way to find out whether they like you, without the ultimatum.
Flirty questions
Flirty without crossing into crude. Specific, embodied, kind.
About this site
The editorial position behind the curation discipline, in more detail.