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01 · Personal & Relational

Questions to Ask a Lesbian Crush

Questions for a woman you have a crush on, arranged from easy openers through to the point where you find out whether she is single, what she is looking for, and whether she wants to go out with you. Written for the situation queer women describe most often: a friendship that might be something else, and no clear way to tell.

21 questions · each with a note on why · conversation guide

The questions

Open any question for the note

  1. What have you been reading or listening to that you cannot stop talking about?

    Why ask it

    An opener that works because it asks for enthusiasm rather than facts. You also get an immediate read on how she talks when she is interested in something, which is the baseline you will compare everything else against.

  2. How do you know most of the people you spend time with?

    Why ask it

    This maps her world without interrogating her: work, an old house share, a team, one central friend who introduced everyone. In small circles it also quietly tells you how many people would hear about it if something happened between you.

  3. What is your week actually like? When are you free?

    Why ask it

    Practical and mildly forward, which is the point. If she answers with real openings rather than a general complaint about being busy, that is a small piece of evidence. If she stays vague twice, believe the vagueness.

  4. What is the last thing that made you laugh until you could not speak?

    Why ask it

    Better than asking what she finds funny, because it forces a specific story and she has to tell it. Whether she can be silly with someone she does not know well yet is worth learning before you plan anything ambitious.

  5. What are you like at home when nobody is coming over?

    Why ask it

    Everyone has a public setting; this asks past it. The answer is the version of her you would actually be spending time with, and it is much more useful than any list of interests.

  6. Are you seeing anyone at the moment?

    Why ask it

    Ask it plainly and early rather than deducing it over weeks. Note whether the answer is a clear no, a clear yes, or a complicated paragraph, because the paragraph is an answer too and it usually means not yet resolved.

  7. Would you rather be asked out directly, or do you prefer to do the asking?

    Why ask it

    This is doing two things at once: gathering information and putting the possibility in the room. It is also a genuine question between women, where the assumption that someone else initiates has no default to fall back on.

  8. Have you ever dated anyone in this circle?

    Why ask it

    Overlapping histories are normal rather than scandalous, and knowing about them beforehand saves an awkward evening later. What matters more is the tone: whether she describes exes as people she still respects or as a list of grievances.

  9. Have you had a friendship turn into something else before? How did that go?

    Why ask it

    The most useful question on this page if you are currently friends. Her answer tells you whether she considers that a good idea at all, and whether the last attempt cost her a friend, which is often the real hesitation.

  10. What are you looking for at the moment, honestly?

    Why ask it

    Adding 'honestly' gives permission for an inconvenient answer, and an inconvenient answer now is far better than one in three months. Take it at face value rather than as an opening position to negotiate with.

  11. What ended your last relationship, in your words?

    Why ask it

    Listen for whether she can describe her own part in it. A story where the other person is entirely at fault is not necessarily untrue, but it tells you nothing about how she handles things, which is what you were asking.

  12. What do you end up arguing about with someone you are seeing?

    Why ask it

    The recurring argument is more predictive than any account of how she handles conflict in general, because everyone describes themselves as a good communicator. Time, money, attention, and other people's opinions cover most of it.

  13. How out are you at work and with your family, and what does that look like day to day?

    Why ask it

    This is the practical question rather than the emotional one, and it has real consequences for anyone dating her: whose photos go on a desk, who gets told about a holiday. Ask it neutrally, and do not treat a cautious answer as a problem to be fixed.

  14. Is your family part of your life, and how does that go?

    Why ask it

    Keeping it open lets her decide how much to say. The answer covers both closeness and acceptance without demanding a story about rejection, and it tells you who is likely to be in the room at Christmas.

  15. What do you need from someone after a bad week?

    Why ask it

    Concrete answers are the good ones: food, silence, being asked no questions, going out anyway. This is the most immediately usable thing you can learn about her, and almost nobody asks it early.

  16. What does a good weekend together look like once things are settled?

    Why ask it

    It skips the first-date fantasy and describes the ordinary version, which is what a relationship mostly is. Whether her picture involves other people or just the two of you is worth noticing, because that mismatch causes more trouble than taste in films.

  17. Who would you want me to meet, and who would you never introduce me to?

    Why ask it

    The second half is the interesting one. There is usually a specific reason: a chaotic friend, a parent who behaves badly, an ex still in the group. It also tells you whether she is picturing you meeting anyone at all.

  18. What are you working on about yourself at the moment?

    Why ask it

    Answers range from a course to therapy to a habit she is trying to break. What matters is whether she can name something without either performing humility or turning it into a list of achievements.

  19. What would make you say no to someone you actually liked?

    Why ask it

    This reaches her deal-breakers from an angle that gets real answers, because it forces her to name what outweighs attraction. Distance, wanting children, a habit she will not live with. Believe the list.

  20. What have I got wrong about you so far?

    Why ask it

    Late-conversation question, and it works because it assumes you have got something wrong. She may name something small, but the correction is usually a genuine invitation to know her better rather than a complaint.

  21. Can I take you out properly? What would you want to do?

    Why ask it

    The point of everything above. Saying 'properly' removes the ambiguity that a friendship-shaped invitation preserves, and asking what she would want to do makes it easy to say yes to something specific. A yes with no suggestion attached, twice, is usually a polite no.

Before, during, and after the conversation

Practical guidance for the conversation itself

Working out whether it is mutual

  • Look at initiation rather than warmth. Plenty of people are affectionate with friends; the signal is whether she starts things, suggests plans, and follows up when you do not.
  • Notice whether she engineers time alone with you. Group friendliness and one-to-one effort are very different pieces of evidence.
  • Count the times you have asked and she has been unavailable. Two vague deferrals with no alternative offered is an answer, even when the words are enthusiastic.
  • Be careful with the intense-friendship reading. It is a well-known dynamic and it goes both ways, which is exactly why guessing has such a bad record and asking works better.
  • If she is a friend, weigh what you would lose. Some people can ask and stay close afterward; some cannot, and it is worth being honest with yourself about which you are before you start.

Asking her out

  1. 1Use an unmistakable word. 'A date' removes the ambiguity that 'hang out' preserves, and the ambiguity is the thing that has been costing you months.
  2. 2Propose something specific with a time attached. An open invitation puts all the work on her and is easy to leave unanswered without either of you deciding anything.
  3. 3Say it in person or on a call if you can. Text makes a warm no easier to send and a real yes harder to read.
  4. 4Give her an easy exit. Something like 'no pressure at all if not' costs you nothing and makes a friendship much more likely to survive a no.
  5. 5Take the first answer as the answer. Asking again after a clear no changes what she has to manage every time she sees you.
  6. 6If it is a yes, book it before the conversation ends. Enthusiasm that never turns into a date is where most of these stall.

What not to open with

  • Her coming-out story. It can be a good conversation later, once there is trust, but as an opener it asks her to hand over the most personal thing she has while you have offered nothing.
  • How she knew she was attracted to women. She has answered this for strangers many times, and being asked again on a first evening is tiring rather than intimate.
  • Questions about the community as though she speaks for it. Ask what she thinks, not what lesbians think.
  • Anything about her body, her past with men, or how she and a partner would do things. If you would not ask a straight acquaintance, do not ask her.
  • A rapid sequence of deep questions. Two or three good ones with real listening between them beats a checklist, which reads as an interview and gets interview answers.