The RelationshipQuestions
Questions to ask a guy

Questions to ask a guy

For getting to know him, whether it is day one or date three.

Whether you just matched, just met, or are a few dates in, the way to know a guy is not to interview him. It is to ask the questions he actually wants to answer.

These move from easy ice breakers to the ones that quietly show you who he is, with a few flirty ones for when the moment is right.

Ask a guy / Ice breakers1 / 72

What would you change about today if you could redo one part of it?

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Ice breakers

  1. 1What would you change about today if you could redo one part of it?
  2. 2What made today better than you expected it to be?
  3. 3What do you do to unwind after a long week?
  4. 4What is something you do purely because you enjoy it, not for results?
  5. 5What is the one thing you always order no matter where you are?
  6. 6Do you text back fast, or are you the slow and mysterious type?
  7. 7Which app is eating most of your time lately?
  8. 8What is something you have rewatched more than once this month?
  9. 9How are you actually doing today, for real?
  10. 10Do you go straight home after work, or take the long way?
  11. 11What is your go-to move when you walk into a party solo?
  12. 12What is something on your phone I would find surprising?
  13. 13When was the last time something excited you way more than it should have?
  14. 14If you had to describe your mood in exactly one word, what would it be?
  15. 15Which place around here do you keep telling people to try?
  16. 16What is something about you I would never guess just by looking?

Getting to know him

  1. 17How would you describe what you do without using your job title?
  2. 18What are you weirdly passionate about?
  3. 19What would your best friend say is your best quality?
  4. 20What have you taught yourself just because you wanted to?
  5. 21What does your friend group usually get up to on a normal weekend?
  6. 22Do you collect anything or geek out over something without apology?
  7. 23How do you usually spend money you did not plan on having?
  8. 24What is a habit from your family you did not realize was unusual until you left home?
  9. 25What can you do that most people your age cannot?
  10. 26What do you do the moment a day completely falls apart?
  11. 27What are you working on that nobody assigned you?
  12. 28What random skill would you love to teach someone else?
  13. 29Is there something you do every single day without ever posting about it?
  14. 30What have you been meaning to start but have not gotten to yet?
  15. 31What is the farthest you have gone out of your way for something you loved?
  16. 32If your friends had to warn someone about you, what would they say?

Fun and playful

  1. 33What is a rumor about you that is somehow completely true?
  2. 34How do you win people over in under a minute flat?
  3. 35Have you ever gone through with a dare you regretted saying yes to?
  4. 36What rule do you break on purpose just because you can?
  5. 37How good is your best party trick, honestly?
  6. 38What is the most chaotic thing you have ever talked a friend into doing?
  7. 39What game turns you into a completely different person the moment it starts?
  8. 40What is the smoothest excuse you have ever gotten away with?
  9. 41Could you nail a costume or character without even trying?
  10. 42How much trouble has your sense of humor gotten you into?
  11. 43What is the fastest way you know to make a total stranger laugh?
  12. 44What is a prank you are still proud of pulling off?
  13. 45Which topic do you always end up turning into a bit?
  14. 46Would you take on a challenge just to prove a point?

A little deeper

  1. 47What is a piece of advice you give others but rarely take yourself?
  2. 48What kind of person do you find yourself becoming around the right people?
  3. 49Which compliment actually lands for you instead of just bouncing off?
  4. 50What do you do when you care about someone but are not sure it shows?
  5. 51Is there a part of yourself you like more now than you used to?
  6. 52What do you keep to yourself even when you probably should not?
  7. 53When did you last realize you had grown into someone completely new?
  8. 54What is something you have stopped explaining to people because they never got it?
  9. 55Do people underestimate how driven you actually are?
  10. 56Who has supported you in a way you still think about?
  11. 57What is a belief about relationships you have changed your mind on?
  12. 58What do you notice about yourself when you are around someone you like?
  13. 59Have you grown more honest about yourself as you have gotten older?
  14. 60What is a version of success that only matters to you, not anyone else?

Flirty

  1. 61What is a version of me you are only now starting to see?
  2. 62Did you decide something about me before I had even said much?
  3. 63What is the exact moment you decided I was not just a stranger?
  4. 64What compliment have you been holding back since we started talking?
  5. 65How far would you actually go if you knew I would say yes?
  6. 66What are you secretly hoping this turns into?
  7. 67What is a text to me you typed out and then deleted?
  8. 68What charming habit of yours do you probably not even notice?
  9. 69Is asking me out something you have actually thought about?
  10. 70Is there something you want to know about me but have not asked yet?
  11. 71What is a line you would never actually have the nerve to use?
  12. 72What kept you from losing interest after our first conversation?

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