Lost for Words? Need some Questions to Ask your Boyfriend?

In the beginning of a relationship, you’re not usually lacking for things to talk about.

But as time passes, it seems like you’ve learned all there is to know about one another. Periods of silence can be difficult. Most topics to talk about with your crush might have been all answered.

Learning about one another builds intimacy between you as a couple. Especially early on, it makes you feel like you’re clicking – you feel chemistry – when you ask questions and find common ground.

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Of course, as time goes by and you and your guy get to know each other, you might feel like you’ve run out of things to talk about. You might even feel as if your relationship is losing momentum because you can’t have those great “Oh my gosh ME TOO” kinds of conversations any more.

Guess what? You can still have those conversations!

I’m here today to bring you a list of things you can talk about with your boyfriend. Some things on this list are for a couple who just met – others are for couples who have known each other for a longtime.

I’ve organized topics to talk about with your crush into categories.

Before we get to the list, I want to provide you with a few of cautions. First of all, this isn’t a list you print and run through over dinner. This is a list of suggestions for when you’re together and it seems like a good time to dig a little deeper.

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Secondly, some of these questions will bring up areas of his past that can make you jealous. DON’T DO THIS! He did indeed have a life before you met, he had other girlfriends and maybe he was even married. That is his past. You also have a past but now, you’re together. If you ask a question about his past, accept his response without jealousy, envy or anger, please!

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Lastly, if you ask him these questions, be prepared to answer them yourself!

Here’s the list of 100 things to talk about with your boyfriend

Fun Things to Talk About With Your Boyfriend

  1. What names have been ruined for you because you knew someone you didn’t like who had that name?
  2. What boggles your mind whenever you think about it?
  3. What’s the spiciest thing you’ve ever eaten and regretted?
  4. Toilet paper – over or under?
  5. If someone challenged you to a dance competition, what song would guarantee your victory?
  6. What’s your favorite lame joke?
  7. If you had no financial restrictions, what would be one thing you would want to try?
  8. What’s the chore you put off the longest?
  9. If I waved a magic wand and gave you the ability to fly, where would you go first?
  10. If you were an action figure, what would your superpower be and what special tools would be on your belt?
  11. Where do you wish you could create a shortcut?
  12. If someone offered you whatever car you wanted, what car would you get?
  13. Of all the products out there, which one do you think needs to be made better?
  14. What event from your past do you wish you could see in video?
  15. If you were crazy rich, what types of crazy or obnoxious things would you do?
  16. If you won the lottery, what’s the first thing you would buy?
  17. If your diet could only contain five things, what would yours be?
  18. Where is the number one place you want to visit?
  19. If you found a genie and a lamp, what three wishes would you make?
  20. Cats or dogs or both?

Personal Things to Talk About With Your Boyfriend

  1. What’s it like to be you?
  2. Tell me one brutally honest truth about yourself.
  3. When do you feel the most like your true self?
  4. If you wrote your story, what would this chapter be called?
  5. What makes you more emotional than you’re comfortable with?
  6. If I wanted the fast-track to making you angry, what would it be?
  7. Tell me what’s on your bucket list.
  8. What do you do that makes you the happiest?
  9. What do you want people to remember you for when you’re gone?
  10. What would your life be like if you lived up to your full potential?
  11. What is the one thing in life that just fascinates the heck out of you?
  12. Who makes you the most uncomfortable when they’re around?
  13. Give me one word that describes you the best.
  14. What do you want to get out of life?
  15. When you catch yourself procrastinating, what do you do to get past it?
  16. Share with me one secret from your past that most people don’t know.
  17. If you had one week to live, what would you do with that time?
  18. If you could spend one day with someone, living or dead, who would you choose?
  19. Do you love or hate animals? Which animal would you want as a pet?
  20. How do you react when you don’t get what you want?

Things to Talk About With Your Boyfriend From His Past

  1. What is the most difficult or painful text you’ve ever sent someone?
  2. What’s the worst thing you’ve done and hidden from your parents?
  3. Tell me about a really awkward moment you had in high school.
  4. If you could have a re-do on one decision from your life, what decision would that be and how would you change?
  5. Tell me about a time when you just threw caution to the wind and went for it, regardless of the consequences.
  6. If you had a recording about your whole life, which hour would you want to go back and watch?
  7. What is the most memorable phone call of your life?
  8. Tell me about something in your life that changed you for the better.
  9. Tell me about something in your life that changed you for the worse.
  10. Have you ever purposefully cut someone out of your life? Why?
  11. What is your most beautiful memory so far?
  12. How different are you from five years ago?
  13. Tell me about the riskiest thing you’ve ever done.
  14. What is the most memorable vacation you’ve ever taken?
  15. What is the story about you that people just love to share?
  16. What was your favorite TV show when you were a kid?
  17. Who did you idolize when you were a kid?
  18. What is the most humiliating moment from your life?
  19. When have you felt the most proud of yourself?
  20. Who was your favorite band growing up?

Relationship Things to Talk About With Your Boyfriend

  1. What is the best way you can think of to spend a day with a loved one?
  2. What would you say is the best and worst thing about having you as a boyfriend?
  3. How do you view the role of a wife?
  4. Tell me one thing a woman can do to become more attractive (excluding change her appearance).
  5. What did you learn about relationships from your parents?
  6. Tell me about the couple you know who has the healthiest relationship.
  7. Are you willing to go to couples therapy if things derail in a serious relationship?
  8. What do you like and dislike most about being in a long-term relationship?
  9. Excluding cheating, what is an absolute relationship-ending incident for you?
  10. Where have your ideas of the ideal relationship come from?
  11. What have you learned from past relationships?
  12. How do you think couples should manage sharing the household chores?
  13. What things do you think cause most couples to grow apart and split up?
  14. How would your exes describe you today if asked?
  15. How would you react if you found out I accidentally got pregnant?
  16. Are you willing to change diapers? Allllll diapers?
  17. City or country boy?
  18. What’s your favorite female body part?
  19. What is the craziest thing you’ve done during sex?
  20. If we argue and you’re truly in the wrong, will you be able to admit it?

Topics to Talk About With Your Crush About YOUR Relationship

  1. At what point did you realize you were in love with me?
  2. What was it about me that first attracted you to me?
  3. The first time you saw me, what did you think?
  4. Of all of our dates so far, what’s your favorite?
  5. How can I make you feel loved in our relationship?
  6. What do I do that drives you crazy, but still makes you smile inside?
  7. What is one sexual fantasy you would like to live out?
  8. What three things do you see between us that make us such a great couple?
  9. Is there something in our sex life that I don’t do but you wish I would?
  10. Is there anything I can change to make me a more perfect partner for you?

Things to Ask Your Boyfriend About His Worldview

  1. Who in your life holds onto a belief or theory that has been proven to be wrong? What is that belief and how do they rationalize holding on to it?
  2. How do you view money?
  3. Is there ever a time to act first and ask for forgiveness later?
  4. Who do you find impossible to take seriously?
  5. What do you wish someone had taught you so you didn’t have to learn it the hard way?
  6. If you could dictate one mandatory class for all school-age kids, what would it be?
  7. What do you think has been considered normal by society, but it shouldn’t be?
  8. Who do you wish you could be more like?
  9. What is your favorite period of history?
  10. What do you wish you could stop doing?

Topics to Talk About With Your Crush Summary

Beware of The Answers

Some of these questions will be very revealing and might contain answers that are red flags. For example, if everything bad that has happened in his life is someone else’s fault, he has a problem accepting responsibility.

If he thinks treating people disrespectfully is funny, he’s probably pretty childish and lacks confidence.

If your guy reveals something particularly disturbing about his past, you might want to consider your next move. Your values should be in alignment.

In summary, these 100 things to talk about are meant to get you thinking about some more topics to explore with your significant other – have fun with them!

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