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50 questions

Questions to ask your crush

Talking to a crush has a specific difficulty. You want to know everything about them and you want to appear to want nothing at all. Most questions fail one of those two tests: they are either so safe that the conversation dies, or so pointed that the intention shows.

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The questions that work sit in between. They are friendly enough to ask anyone and open enough that the answer tells you something real. Just as usefully, they give the other person an easy way to ask you something back, which is the only signal worth reading. Someone who is interested returns the question.

A warning that is also a relief: no question will make someone like you. What these do is keep a conversation alive long enough for both of you to find out. The last section is for when you are fairly sure and want to be a little braver.

Easy openers

Things you could ask anybody. The trick is to follow up on the answer, not to move on to the next question.

  1. 1What are you up to this weekend?
  2. 2What have you been watching lately?
  3. 3How do you know everyone here?
  4. 4What is the best thing you have done this year?
  5. 5What are you listening to at the moment?
  6. 6What do you do when you are not doing this?
  7. 7Where is the best place to eat round here?
  8. 8What would you recommend I read, watch or listen to?
  9. 9What is your plan for the summer?
  10. 10What was the highlight of your day?

Getting to know them

A step closer. These show you are interested in them and not only in the conversation.

  1. 1What were you like as a kid?
  2. 2What are you really into that most people do not know about?
  3. 3What is your family like?
  4. 4What would you do if you did not have to work?
  5. 5What is the best trip you have ever taken?
  6. 6What is something you are proud of?
  7. 7Who do you look up to?
  8. 8What is a skill you wish you had?
  9. 9What is your favourite way to waste time?
  10. 10What is something you have always wanted to try?

Questions to ask over text

Short, specific and easy to answer in a line. Text is a poor place for anything deep.

  1. 1What are you having for dinner?
  2. 2What are you watching tonight?
  3. 3What topping does not belong on a pizza?
  4. 4What song should I listen to right now?
  5. 5What is the worst film you have ever sat through?
  6. 6What are you doing instead of what you should be doing?
  7. 7What would you rather be doing right now?
  8. 8Seen anything funny today?
  9. 9What is your go-to karaoke song?
  10. 10What is the best thing about your week so far?

Finding out if you would get on

Light compatibility questions, asked as curiosity.

  1. 1Are you a morning person or a night person?
  2. 2What does your ideal Saturday look like?
  3. 3Would you rather go out or stay in?
  4. 4What kind of holiday do you like?
  5. 5What do you look for in the people you spend time with?
  6. 6What is something that always makes you laugh?
  7. 7How do you feel about surprises?
  8. 8What is a small thing that annoys you more than it should?
  9. 9What is the best way to cheer you up?
  10. 10What do you like doing on a first date?

A little braver

For when you are fairly sure. These lean towards showing your hand, so read the reply before sending another.

  1. 1What is your type, if you have one?
  2. 2What is the best date you have ever been on?
  3. 3What do you find attractive in someone that is not about looks?
  4. 4Has anyone ever told you that you are easy to talk to?
  5. 5What would you say if I asked you out for a coffee?
  6. 6What is something you like about me?
  7. 7Do you believe in making the first move?
  8. 8What were you thinking the first time we talked?
  9. 9Who was your first crush?
  10. 10Are you seeing anyone, or should I keep asking you questions?

Keep asking without having to remember

The hard part of this is not the questions, it is the habit. Most couples read a list like this, have one good conversation, and never open it again. HeartTap exists mainly to remove that failure: it sends one question at a time to both of you, and hides each answer until you have both written yours, so neither of you drifts toward agreeing with the other.

If you would rather not choose, the couple question generator picks one at random from every set on this site.

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Frequently asked questions

What should I ask my crush to keep the conversation going?

Open questions about what they like doing, followed by a real follow-up on whatever they say. The follow-up matters more than the question. People remember being listened to much longer than they remember being asked something clever.

What are good questions to ask your crush over text?

Short ones with easy answers: what they are watching, eating or avoiding doing. Text suits quick back and forth, so keep each question to a line and save anything that needs a paragraph for when you are talking in person.

How do I know if my crush likes me back?

They ask you things in return, they keep the conversation going when it could end, and their answers get longer over time. One-word replies with no question back are an answer too, and it is kinder to yourself to read them as one.

How do I ask questions without making it obvious I like them?

Ask the kind of thing you would ask a friend you were curious about, and share something of your own each time. A conversation with both people talking does not look like an interrogation. That said, being a little obvious is not a disaster. It is how most things start.

One question a day, answered together

HeartTap delivers a question at a time from a library of over 2000, and keeps both answers hidden until you have each written yours. Free on iPhone and Android.

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