100 Things to Talk About With Your Boyfriend

At the beginning of a relationship, you have plenty of things to talk about with your boyfriend, but as time passes, it’s more challenging. Finding things to talk about with your crush after a few months doesn’t need to be so hard!

In older relationships, periods of silence can be difficult. Many common things to talk about have already been answered.

And yet, learning about one another builds intimacy, especially early on. It makes you feel like you’re clicking and there’s chemistry. That’s how you find common ground and continue to grow as a couple.

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But, as time passes, you might feel like you’ve run out of things to talk about with your boyfriend. You might even feel your relationship is losing momentum because you can’t have those great “Oh my gosh, ME TOO” conversations anymore.

Guess what? You still can have those conversations!

How to Use this List

This isn’t a list you print and run through over dinner. Instead, treat it as a list of suggestions to use when you’re together, and it seems like an excellent time to dig a little deeper.

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Also, be aware that some of these questions will bring up areas of his past that can make you jealous. DON’T DO THIS! Jealousy is a trait for low-confidence women!

He had a life before you met; he had other girlfriends and may have been married. That is his past. You also have a past, but now, you’re together. If you ask a question about his history, accept his response without jealousy, envy, or anger, please!

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

100 Things to Talk About With Your Boyfriend

Below, you’ll discover 100 things you can talk about with your boyfriend. Some items on this list are for a couple who just met, while others are for couples who have known each other for a long time.

These things to talk about with your crush are organized into categories to make it easier to find a question to fit the situation. Each one, in and of itself, can produce either a meaningful or fun conversation, depending on the topic. But, beware of digging into a part of his past he might not want to resurrect. If he seems hesitant to ask, back off and shift the conversation to something safe.

Fun Things to Talk About With Your Boyfriend

These topics are fun and shouldn’t scare up any skeletons; they’ll still allow you to get to know one another better.

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. What song would guarantee victory if someone challenged you to a dance competition?
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 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 the video?
15. If you were crazy rich, what types of crazy or obnoxious things would you do?
16. What would be the first thing you would buy if you won the lottery?
17. What would yours be if your diet could only contain five things?
18. Where is the number one place you want to visit?
19. What three wishes would you make if you found a genie and a lamp?
20. Cats or dogs or both?

Personal Things to Talk About with Your Crush

These topics are a bit more personal and might scare up something your guy doesn’t want to discuss right now. It might be too soon for your relationship, or it may be something he isn’t ready to discuss yet.

He may change his mind when he feels safer.

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 make 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 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 procrastinate, what do you do to get past it?
16. Share one secret from your past that most people don’t know.
17. What would you do with that time if you had one week to live?
18. Whom would you choose if you could spend one day with someone, living or dead?
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

Things to talk about with your crush get tricky when you start tromping around in someone’s past. Make sure he’s in the right mood to discuss topics like these before you dive in. 

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 an 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 improved you.
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 story about you do people love to share?
16. What was your favorite TV show when you were a kid?
17. Whom did you idolize when you were a kid?
18. What is the most humiliating moment in your life?
19. When have you felt the proudest of yourself?
20. Whom was your favorite band growing up?

Relationship Things to Talk About with Your Boyfriend

These topics are best saved for when your relationship is a little older because some of these questions ask about a long-term future with you. If he isn’t ready, he might freak out a bit. Don’t worry; you’ll know when the time is right.

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 changing 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 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 to share the household chores?
13. What things do you think cause most couples to split apart?
14. How would your exes describe you today if asked?
15. How would you react if you discovered 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 genuinely in the wrong, will you be able to admit it?

Topics to Talk About with Your Crush Regarding Your Relationship

These topics to discuss with your boyfriend are for later in your relationship. They’re probing into topics around the “L” word, so make sure you’ve said it to one another before you ask him about it.

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 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 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 perfect partner for you?

Things to Ask Your Boyfriend About His Worldview

These are great questions early in a relationship because they help you get to know the guy you’re with. They aren’t too probing or personal, yet they provide insight.

1. Who in your life holds onto a belief or theory that has been proven 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 shouldn’t be?
8. Whom 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?

100 Things to Talk About with Your boyfriend

Some of these questions are very revealing and might contain answers that raise a few red flags. For example, if everything wrong 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 childish and lacks confidence.

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

These one hundred things to discuss with your boyfriend are meant to get you thinking about more topics to explore with your significant other, so have fun with them!

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