65 Thought-Provoking Things to Say to Your Boyfriend When The Conversation Gets Boring

Last updated on April 13, 2024 by Michelle Devani

Do conversations with your partner grow stale?

Are you running out of things to talk about? 

Are you looking for ways to spice up your conversations?

If so, keep reading because this guide is packed with ideas for engaging conversation topics.

Simply browse the list below, pick your favorite topics and introduce them whenever the chat is becoming a bit stale. 

However, before you do that, I need you to read the following sentences carefully. 

If you’re bored of conversations with your partner, there’s every chance he’s bored too. 

When a relationship gets to this point, it’s normal to start worrying that he’s looking at other women.   

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When The Conversation Gets Boring

Today, we are going to have a conversation about interesting things to say to your boyfriend when the conversation gets boring, so you can spice up your love life! 

You don’t have to worry about things going stale in the communication department with your boyfriend any longer because we will be looking at 65 things to say to your boyfriend!

Do you feel like you and your boyfriend are struggling to find things to talk about? Do you sit in silence often? Are you wondering if the spark in the relationship has faded away? 

We’ll talk more about your relationship with your boyfriend in this post, so you can analyze what has maybe changed in the relationship to make you think the conversation is boring now.

You might want to think about whether you really want to be in a relationship with your boyfriend if the two of you have quit talking. 

Is this relationship worth saving? Do you feel like he still thinks you are interesting? What has changed in the relationship to make it where you can’t talk like a normal couple anymore? 

Think about these things as you read this article!

Things to Say to Your Boyfriend When the Conversation Gets Boring

So, things have gotten a little old in the conversation department in your relationship. That’s not the end of the world; trust me! Worse things could be going on in your relationship! 

If you are struggling with communication, you may just be going through a dry spell. That’s a normal part of any relationship. You just need to find some new topics to discuss. 

This list will surely give you plenty of things to talk about. You could plan a road trip and have fun going over the topics listed below as you drive to a fun destination. Have you considered reading a book together? 

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You could each read a chapter, and then you could discuss your take on what the author of the book really meant by what was written. That’s one way to talk!

Another thing you can do if your talking has gotten stale is to watch television together. Discuss what you are watching while it’s on, too. You might say, “I bet he’s doing this next,” or “He’ll definitely say this in the next scene!” You can kind of play a game to see which one of you can guess what will happen next on the show or movie. It’s really fun! Trust me!

what were your dreams when you were growing up
  1. What were your dreams when you were growing up? How do you feel they have panned out now that you are an adult? What do you have left to do to accomplish them? What are your dreams today?
  2. What would you do if I got pregnant? Would you like to have a baby someday?
  3. If you could have three wishes, what would they be?
  4. What are the top reasons that you think break a couple up? What do you think might break us up one day? What reasons would you break up with me?
  5. What is something you’ve always wanted to tell me but have been too shy to bring up? Please share all of your secrets with me.
  6. What do you believe are your greatest strengths and weaknesses?
  7. Do you believe in God? What is your faith like?
  8. What do you think about the most? What is your passion, biggest hobby, or most ambitious goal in life?
  9. What is your favorite movie and TV show? Why is it your favorite? What is your favorite episode or scene, and why is it your favorite?
  10. Where would you like our first road trip to be? Where would you like our next one to be? Do you think we could plan it now? What would we do there?
  11. What is your dream vacation destination?
  12. Do you have any secrets from me? Why haven’t you shared them yet? I’d love to hear all about them!
  13. What is your most embarrassing story? Have you ever gone to the bathroom outside of an actual bathroom?
  14. What are your biggest pet peeves? Is there anything that I do that bothers you?
  15. If you could star in a movie as a superhero, what would you do? What would your powers be?
  16. What was your most serious romantic relationship? Were you in love? Why did the two of you break up? Do you ever think about her? Do you still stay in contact with her?
  17. What’s the funniest story you’ve ever heard? Have you ever wet your pants because you were laughing so hard?
  18. Would you pray with me and/or go to church with me?
  19. If you won the lottery, what would you do with the money? Do you play the lottery? Do you believe it’s okay to gamble?
  20. If you could change one thing about me, what would it be? Do you think that is something I could change about myself?
  21. What are your friends and family like? When can I meet them?
  22. What is the biggest hurt you’ve ever had? Did you cry? When was the last time you did cry?
  23. What excites you the most in life?
  24. Would you rather travel to Paris or Vegas? Let’s say cost doesn’t matter. What would you do at each location?
  25. What is one accomplishment you have yet to achieve?
  26. Do you think we’d make a good couple in marriage?
  27. What has been the happiest day of your life? Why was it such a good day? What made it different from your average day?
  28. What was your most prized possession as a child? Do you still have it?
  29. What is the weirdest thing about you? What is the weirdest thing about me?
  30. What is the strongest political view you have? Are you super political? Do you think it’s important to have political views? Are you okay with mine?
  31. What is the best advice you’ve ever heard? Who gave it to you? Why was it the best advice ever? How has it affected your life?
  32. Have any of your dreams and wishes come true as an adult? Which ones do you have yet to accomplish? What steps are needed to reach your goals?
  33. What is your dream job? What do you think you need to do to get yourself in that job? What skills or education are you lacking? Do you think one day you will make it to that point? What do you think about my job? Do you think I was meant to do what I’m currently doing? I’d love to hear your thoughts on my career path!
  34. In marriage, what do you believe are grounds for divorce? Have you ever been married? Are your parents still married? If not, why did they get a divorce? How did you feel about the divorce? Do you have step-parents? Do you get along with them? Why or why not?
  35. What do you believe the biggest challenge is in our relationship? How do you think we can overcome it?
  36. If you could have the answers to questions about the future, what would you want to know?
  37. What five words would another guy use to describe you? What about an ex-girlfriend? What would she say about you?
  38. Would you be willing to take a compatibility test with me? How compatible do you think we are?
  39. Do you believe in destiny? Do you think fate brought us together? How do you think destiny picked you and me to be together? What do you think made us such a good match?
  40. What made you fall in love with me? Would you like to hear why I fell in love with you?
  41. Which is worse - silence, boredom, or random conversation?
  42. Do you believe horoscopes can tell the future? Do you think your Zodiac sign is accurate?
  43. Do you think we have problems with communication? Do you feel like we have gotten boring?
  44. What was your worst date? What happened? Where did you take her? What did you do? Who was it with? How did it end?
  45. Who was your first crush? Do you still talk to that person?
  46. What would you change about the past? Do you think our mistakes shape us into the people we are today?
  47. What is your favorite website? Why is it your favorite? 
  48. Who was your first pet? How did he or she pass away? Do you love pets? Would you like a cat or dog one day?
  49. What cause do you think is the most worthy? Do you like volunteer work? Do you think people do enough volunteer work in this world? What do you think is the worst thing people do?
  50. How do you think the Sopranos show ended? What was your favorite ending to a series on television? Why was it your favorite?
  51. Would you rather go to a sporting event or a charity one?
  52. If your house is on fire, what are five material possessions that you would like to save?
  53. Want to hear something that happened to me today?
  54. What are 3 food you can't live without?
  55. What is your weirdest habit?
  56. If money is not a problem what would you be doing with your life right now?
  57. Do you have anything in mind that you've been dying to try?
  58. Have you ever take any personality test? (You can then continue to discuss on the result, or take one if your significant other never take any)
  59. If you had to choose between money and love, what would you choose and why?
  60. If you could go anywhere in the world, where would you go?
  61. What is your favorite quote? 
  62. What is your favorite month of the year and why?
  63. What’s the first thing that you think when you see a homeless person?
  64. What was the thing that makes you attracted to me in the first place?
  65. What was your first impression of me?

Being In Love With Your Boyfriend

being in love with your boyfriend

One consideration you should make is whether you are actually in love with your boyfriend and vice versa. Do you think the two of you are meant to be together, or is this just a fling? Do you think that you two go well together and are just having trouble talking right now? It’s important to ask yourself these questions so that you can determine if you think he is worth it.

If you are head over heels in love with your boyfriend, then it’s okay to think about how your conversation is going. You will want to fix things so that the two of you can live a fairy tale life together, right? I mean, you don’t want to be in a relationship where you have nothing to say to one another. That would make road trips very boring because you’d drive in silence.

I’ve been on trips like that, and they aren’t very fun! It’s much better when you have plenty of things to say to one another. What could you say to spark a great conversation? Think about it. Have a list ready like the one prepared in this article before you go on a trip with your man.

If you don’t think you are in love with your boyfriend, maybe you should determine if you want to continue in this relationship. Should the two of you part ways, or is this relationship going somewhere special? If you are unsure about the status of your relationship, you should talk to your boyfriend to see what he thinks. That would make for a very interesting conversation!

How Do You Show Love?

One important consideration when thinking of what to say to your boyfriend is how you each communicate. What is your love language? How do you show love to one another? Maybe you enjoy buying gifts for your boyfriend to show him you are thinking of him and love him. Perhaps, you just really enjoy watching his face light up when you bring him home a prize!

Maybe his love language is different than yours. If so, this could be the reason that your conversations have gotten a little stale. You just need to understand one another’s needs better. For example, you could read about love languages to determine what yours is. Then, ask him if he believes that is true. He can probably verify what his love language is as well. 

If he identifies his love language as being quality time, he may need you to make more time for him. If you think he wants to talk during that quality time, you may want to use the list in this article to have plenty of things to talk about with each other in your relationship. Can you bring up those topics without him getting upset over the subjects? That’s another important thing.

Determine How to Bring Up Topics

You may find it helpful to talk about the problems you think you have with your boyfriend or a counselor. Talking to a third party may help you discover if there are unresolved issues in your relationship that need to be addressed. Sometimes, an outside perspective can help you see things you wouldn’t have noticed otherwise! Take him with you if you feel it’s necessary!

If you think you can handle things on your own, go ahead and talk to your man. Ask him what he thinks about your communication. Determine if he thinks you two have a problem or not. If he agrees that things have gotten boring, he may have some suggestions as to what you can do about it. Ask him if there is anything he would enjoy talking about that you haven’t discussed.

When you bring up the 65 questions listed above, take your time and discuss each one as it comes up in a natural way. It’s important that you ask open-ended questions so that he can’t just answer with a yes or no, but instead must speak a few sentences at a minimum. If you can, come up with follow-up questions to each question. That way, the conversation will continue.

How to Bring Up Any Topic

how to bring up any topic

One thing you can do if you are struggling to talk to your man is to be confident. Show a big smile when you are ready to talk about a new subject. Just push your shoulders back, and tell him that you want to talk about something. Let him know that you really want to have a serious discussion and need to talk to him about some things. Then, start going through the list!

Another thing you can do is to put away any distractions. Put away the computer, phone, tablet, television, and any other distracting devices. You want him to know that this is a one-on-one talk between just the two of you. You also want him to know that you are ready to pay close attention to everything he has to say because you want to hear his thoughts and ideas.

Finally, talk about important things after having sex. Sometimes, when guys are thinking, they just have that one thing on their minds. They don’t really want to talk about all of these subjects. They’d rather be having sex. So, if you wait until after you are done having sex, he will be more open to talking about things and having a real conversation about any topic in the world!

How to Listen to Your Boyfriend

Listening is a crucial skill when it comes to asking these questions. You don’t want to just ask one question and then move on to the next one. Instead, you need to listen to his tone, mood, attitude, and body language. Pay attention to everything. Try to put yourself in his shoes when he’s talking so that you can best understand where he’s coming from.

Make sure when he is talking that you don't interrupt. Instead, listen closely and intently to what he is saying and think of any follow-up questions you have that you would like to know the answer to when he's done talking. Make sure that you aren't thinking about what you want to talk about next but instead are listening closely to what he means when he's talking. 

Show your boyfriend that you are paying attention when he’s talking by showing him open body language. This means not having your arms or legs crossed. Nod your head as he tries to get you to understand what he’s saying. This shows him that you are paying close attention. You can start thinking of what you want to say next as he wraps up his words.

When you do speak, make sure they are relevant questions that relate directly to what he’s said. Ask meaningful, thoughtful follow-up questions that will help the two of you continue the conversation. You might even paraphrase something he’s said to show that you paid attention and to verify that you understood what he meant when he was speaking.

What Has Changed In The Relationship?

If the two of you aren’t talking a lot or having nothing new to say to each other, has something changed in your relationship? Do you think one of you is having an affair? If that’s the case, you may be getting your stimulating conversations outside of the relationship, and that might not be fair to your boyfriend (or to you if he is the one having a relationship outside of yours).

You might ask your boyfriend if something has changed in your relationship. Find out what the problem is and if there is a problem that he has identified already. He may know what’s going on and could provide you with valuable insight as to what needs to change to get things back to how they used to be. Do you think that might help your relationship?

Another possibility is that you have just run out of things to talk about. There’s really nothing wrong with that. You just need to spice things up by talking about new topics. What is the latest television series one of you has watched that you can share with the other? What is your viewpoint on everything that is happening on the news?

Talk more about your hope, dreams, goals, aspirations, and ideas about the future. What has changed? You surely don’t want exactly the same thing you wanted ten years ago, right? So, you do have plenty of things you can talk about; you just need to get creative and think about what has changed in your life and what you can share with your boyfriend.

Is He Still Interested In You?

is he still interested in you

This is a very interesting question to think about. If you are both in a place where you are comfortable with each other, that’s great! However, you need to consider whether you are actually still interested in one another? Do you enjoy spending time with your boyfriend? Does he seem to want to be around you? Ask him what’s on his mind and why he’s so quiet.

If he has no desire to talk about the serious topics in life that need to be discussed, especially if they are imperative to your relationship, he may no longer be interested in you. Have you asked your boyfriend what he wants out of life and whether you are still the dream girl he once hooked up with? Find out if he’s still in love with you to determine if you should stay together or not.

If you think or he’s said he is no longer interested in you, it may be time to end things and not worry about getting your boyfriend to open up by asking him a million questions. Instead, end the relationship on the best terms you can. Return each other’s belongings and say goodbye. You may find it helpful to stay apart from one another for a certain period of time. 

After you’ve had time for closure and healing, you can talk about pursuing a relationship that is made of friendship. After you’ve had time apart, you may even discover that you actually did belong together, and you’ll return in each other’s arms. Do you think your relationship is worth saving? What caused the problems your relationship experienced? Resolve those issues!


What do you say when your conversation gets boring?

Ask him random questions if you are having communication issues. Some questions to ask include: What does your dream home look like? Would you ever live in a mobile home with me? Do you like it when I text you during the day? What is your favorite form of communication?

What do you do when your boyfriend is a dry Texter?

Ask your boyfriend if he thinks you are having a lack of communication or having difficulty finding things to talk about. Let the guy know that you’d love it if he’d send you longer texts. He may have walls built up due to past hurts, so make sure you’re understanding.

How do you spark a boring conversation?

Ask random questions and have conversation topics ready to go. Maybe make a list of things to talk about before you see your boyfriend. He may just not be in the mood to talk. In that case, you may want to turn to a friend to find things to talk about.

How do I not be boring when texting?

Always ask questions and share ideas when talking to your boyfriend. Ask your boyfriend how his day is going. Asking open-ended, random questions can surely be a conversation starter for your boyfriend. Ask your best friend for things to talk about with your boyfriend. She may have new ideas!

How do I make him worry about losing me?

The best ideas I know of are to play hard to get and give radio silence. That means giving your boyfriend space. Stay busy and show him that you have a life. Do not ask your boyfriend if he’s worried about losing you. Be a mystery in the relationship.

To Sum It All Up

What do you think of my list of things to say to your boyfriend when the conversation gets boring? What do you talk about with your boyfriend? Do you have an in-depth conversation, or are random words spoken? Ask your boyfriend what he thinks about your relationship’s conversation status!

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Michelle Devani
My name is Michelle Devani, and I've been helping people with their relationships since 2003. In 2017 I decided it was about time I started a blog on the topic, and since then more than 2 million people worldwide have read my relationship advice. Drop me a comment below to let me know what you think.

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