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Getting to know him: 80 questions to ask a guy

by eharmony Editorial Team - November 22, 2023

Whether it’s the first date or you’re six months in, there’s always room to get to know someone better. It can be hard thinking of good questions to ask a guy – which is where this article comes in. Regardless of what stage yourrelationship is in, dating or long-term, you’ll find plenty of interesting questions to ask a guy.

What are good questions to ask a guy?

It depends – on the guy, on the relationship, on the circumstances. As a general rule, start with easy, light-hearted questions, and go deeper as the relationship progresses and you build trust. Open-ended questions are preferable, since they give people space to answer in detail if they want to. It’s also important to ask follow-up questions to show you’re interested.

Flirty questions to ask a guy

Whether you’re preparing for a first date or a little further along and want to take things to the level, flirty questions are a fantastic way to make your interest known without being obvious, especially when you say them in a teasing tone. Some flirty questions to ask a guy:

  1. What do you notice first about a person?
  2. What do you think are your best features?
  3. What is the best and worst pick up line that you have ever heard or used?
  4. Do you prefer it when I’m naughty or nice?
  5. What’s something we have never done together that you would like to try?
  6. What one thing about our relationship that you hope will never change?
  7. What’s me something I don’t know about you, no matter how small?
  8. Can you tell me the story of our first kiss?
  9. How many times did you want to ask me out before you finally did?
  10. What sets me apart from other people you’ve dated?

Questions to ask a guy to get to know him

It can be difficult to get to know a guy but open-ended questions are really useful; they are good ways to prompt your partner into sharing information he might not otherwise realize you want to know about him.

  1. What’s the best thing you’ve read in the last five years?
  2. If you could only bring three things with you on a deserted island, what would you pick?
  3. What do you feel most passionate about?
  4. Who is the most important person in your life and why?
  5. What is something people would never guess just by looking at you?
  6. Can you tell me about your best friend?
  7. What is the weirdest thing you’ve put on a sandwich?
  8. If you could be any animal, for a day, what would you be? And why?
  9. Are you a night owl or an early bird?
  10. How did your last relationship end?

Personal questions to ask a guy

As your relationship progresses, really getting to know your partner becomes more and more important. This is especially true if you’re planning on the relationship being a serious one, since your partner’s views and lifestyle could have an impact on yours for years to come.

  1. Can we talk about our health histories?
  2. Have you ever been in therapy?
  3. How do you approach finances? Do you have debt? What are your financial goals?
  4. What role will your family play in our relationship?
  5. What are you afraid of?
  6. What is something you wish you hadn’t done?
  7. What do you want to improve or change about yourself?
  8. What’s your relationship like with your family?
  9. What’s your favorite way to destress from work?
  10. How do you feel about surprises? Do you like to be surprised?

Questions to ask a guy you like

Those initial stages of getting to know a guy are so much fun… but it can be hard to think of questions to ask that are personal but not too much so, that’ll give you an idea of his personality without being too pushy or nosy. Ask him about his likes and dislikes, his friends, or what he likes to do and save the deep stuff for later.

  1. What’s something you’re looking forward to?
  2. What’s the best compliment you’ve ever received?
  3. Are you a dog person or a car person?
  4. What’s the best new artist/song you’ve discovered recently?
  5. What’s something you wish would go out of style forever?
  6. Are you someone who likes to plan ahead or be spontaneous?
  7. Would you say you’re a superstitious person?
  8. How did you and your best friend meet?
  9. What is the best concert you have ever been to?
  10. What’s the worst movie you ever saw?

Questions to ask a guy over text

More and more people are switching over to text, and for good reason – it lets you take your time answering, you can send people links, and the other person can’t see your reaction, meaning it’s a great avenue for both silly and serious questions.

  1. Would you rather date someone who is exactly like you or the complete opposite?
  2. What’s the most embarrassing thing you’ve ever said or done in front of someone you liked?
  3. What word would you use to describe yourself if you had to choose only one?
  4. What are some of the questions you wish people would stop asking you?
  5. Who haven’t you seen or spoken with in a long time who you hope is doing well?
  6. When was the last time you did something that took you out of your comfort zone?
  7. What is your favorite emoji?
  8. What emojis would you use to describe yourself?
  9. Why did you vote for [his preferred party or candidate]?
  10. What is a fact that you’re shocked more people aren’t aware of?

Deep questions to ask a guy

At some point, the time comes when you really want to know what makes your significant other tick. Deep questions like the ones on this list are a great way to spend some free time getting to know each other better – you could even order in food and make a date night of it.

  1. When was the last time you did something that took you out of your comfort zone?
  2. Do you believe in soulmates?
  3. What would you say are your three most important values?
  4. What traits do you think are most important to find in a partner?
  5. What would you like people to say at your funeral?
  6. What’s your relationship to religion?
  7. Would you rather have a job that’s just a job but pays well, or be paid less to do something you’re passionate about?
  8. What does your dream life look like?
  9. Do you think it matters more what we achieve or who we surround ourselves with?
  10. What are some things you wish you had known when you were younger?

Funny questions to ask a guy

Guys love someone who makes them laugh, and this set of funny questions to ask a guy will have you both chuckling in no time. A light-hearted question is a great icebreaker, plus it can often give you insights into his personality that more serious ones might not.

  1. What’s the weirdest thing that happened to you this week?
  2. What’s your favorite meme of all time?
  3. Would you rather give up carbs or making out?
  4. Are avocados overrated?
  5. What is your favorite urban legend that you believe is true?
  6. If you were to win an Olympic medal, what would it most likely to be for? (Note: it does not have to be a traditional Olympic sport.)
  7. If you could have an unlimited supply of one food, what would it be?
  8. What’s the strangest thing you’ve ever eaten?
  9. Would you rather be on a survival reality show or a dating game show?
  10. Is a hot dog a sandwich?

Relationship questions to ask a guy

Communication is one of the cornerstones of a successful relationship, which is why it’s important for you and your partner to ask each other questions (and answer them honestly) right from the get-go. Plus, being clear about your expectations means there will be fewer unpleasant surprises waiting for you as the relationship progresses.

  1. Would you consider yourself a Relationship Person, or someone who’s generally more comfortable single?
  2. In relationships, are you someone who moves pretty quickly or takes things slow?
  3. Would you rather date someone who is exactly like you or the complete opposite?
  4. What’s something unexpected that you find attractive?
  5. Do you believe in love languages? What’s yours?
  6. Is other people’s approval important to you?
  7. Do you have any relationship deal-breakers?
  8. What traits do you think are most important in a partner?
  9. Are there couples whose relationships you admire? Why?
  10. What is the worst thing about dating these days? The best?

Explore further questions to ask

Getting to know each other is an integral part of the dating process, but it can be very hard to know what kind of questions to ask. Next to the already explained questions, we’ve covered a range of topics, each with plenty of example questions to ask to get to know someone. 

Ask and ye shall receive, even – or maybe especially – in relationships.

Knowing what questions to ask a guy – and being able to ask them at the right time – is an important tool when it comes to dating and finding a deeper connection with your partner. However, that doesn’t mean every conversation needs to be an interrogation – keep it natural and let the conversation flow organically. Speaking of conversations, at eharmony, we take great care to give our members the opportunity to get to know each other with different communication tools. So, start free today to meet singles and find a deeper connection.

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