Being in a Relationship

129 Things to Talk About With Your Boyfriend to Strengthen Your Connection

Milena J. Wisniewska Avatar

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    Never run out of things to talk about with your boyfriend or husband thanks to my ultimate list of conversation starters. This mix of prompts and questions will give you plenty to chat and laugh about, like who knew that you both had that fear of being chased by geese?

    Things to Talk About With Your Boyfriend

    • Talk about the last book or movie that really moved you.
    • What’s the one hobby you’ve always wanted to try but haven’t yet?
    • If you could live in any country for a year, where would it be and why?
    • Tell me about the best vacation you’ve ever had.
    • What’s something you’d love to do on a date and why haven’t you done it yet?
    • Do you have a dream career you haven’t pursued?
    • Share a random fact that never fails to amaze you.
    • What’s a childhood toy or game you wish you could play again?
    • Tell me about a family tradition you loved growing up.
    • What’s your favorite way to relax after a stressful day?
    • Have you ever had a dream that felt real and stayed with you?
    • What skill do you find the most impressive?
    • Describe the perfect weekend for you.
    • Who was your childhood hero?
    • If you could relive any year of your life, which one would it be and why?
    • What’s something you think everyone should try at least once?

    Asking your boyfriend thoughtful questions and using prompts like these helps keep the conversation going and strengthens your connection. Discussing life goals, dreams, and personal experiences can spark deeper conversations and bring you closer, no matter how short or long you have known each other. 

    Random Things to Talk About

    • Describe your perfect lazy day.
    • What’s the weirdest food combination you love?
    • What’s the most random thing you’ve googled recently?
    • If you could switch lives with a celebrity for one day, who would it be?
    • What’s the funniest joke you know by heart?
    • Tell me about a strange coincidence you’ve experienced.
    • Have you ever experienced a night terror?
    • Share your thoughts on astrology.
    • Tell me a story from your childhood that still makes you cringe.
    • If you had a time machine, would you travel to the past or the future?
    • What’s the strangest thing you’ve ever eaten?
    • If animals could talk, which animal would be the funniest to have a conversation with?
    • What’s the most random item you’ve ever bought online?
    • What conspiracy theory seems the most plausible to you?
    • What’s the weirdest thing you’ve ever seen happen in public?
    • Theme song for your life. First thing that pops into your head!
    • What’s the one thing people argue about that seems ridiculous to you?

    This list of random things to talk about is perfect for keeping the convo playful and fun. Asking your boyfriend about quirky topics like strange food combinations or cringy childhood stories can lead to a creative conversation that keeps things lighthearted while helping you discover new sides of each other.

    Fun Things to Talk About to Keep a Conversation Going

    • Describe your dream holiday in one sentence.
    • What’s the funniest nickname you’ve ever had?
    • If you had to perform in a talent show, what would your talent be?
    • What’s your go-to karaoke song?
    • Tell me about the most ridiculous thing you’ve ever done.
    • Describe your favorite pizza topping combination.
    • What would your wrestler name be if you had one?
    • If you could create a new holiday, what would it celebrate?
    • Tell me about a time you laughed so hard you cried.
    • What’s the silliest dare you’ve ever done?
    • Choose the best animal and justify your choice.
    • What’s the strangest fashion trend you’ve ever seen?
    • What’s your funniest memory from school?
    • Tell me about a time when you were caught in a hilarious misunderstanding.
    • What’s your guilty pleasure TV show or movie?
    • What’s the most spontaneous thing you’ve ever done?

    This list of fun things to talk about is filled with lighthearted and entertaining topics of conversation to keep your connection with your boyfriend lively. 

    From fun questions to ask about guilty pleasure TV shows to recounting hilarious misunderstandings, these prompts help you both share fun memories and moments. 

    They offer one of the best ways to get to know your boyfriend better and strengthen your relationship by keeping the conversation flowing effortlessly.

    Cute Conversation Topics

    • What’s the sweetest thing you remember from when we first met?
    • Describe our perfect date night without using the word 'romantic.'
    • What’s the most adorable thing you’ve ever seen a child or pet do?
    • Share a memory of us that always makes you smile.
    • If we had a pet together, what would you name it?
    • What’s one thing you love about me that you haven’t told me before?
    • Talk about the little things we do together that bring you joy.
    • If you could write a love letter to me, what’s one thing you’d include?
    • Tell me about something you think we’ll laugh about years from now.
    • What’s the first thing you thought about me when we met?
    • Imagine we’re a famous couple — who would we be and why?
    • What’s your favorite way to cuddle?
    • Describe something I do that always makes you smile.
    • What’s your favorite memory of us so far?
    • Explain what you think is our cutest habit as a couple.
    • Share the thing that makes you feel close to me.

    This blended list of questions to ask your boyfriend and prompts offers both fun and meaningful conversation topics that will help you deepen your connection. From light-hearted moments to deep questions, these prompts help you discover new things about each other and keep the conversation going.

    Mature Topics to Talk About

    • Tell me about a book or documentary that changed your perspective on something.
    • What’s a personal project or hobby you’ve always wanted to start but haven’t yet?
    • How do you balance staying informed about world events with not feeling overwhelmed?
    • Share one habit you've adopted recently to improve your well-being.
    • What’s your take on the rise of remote work and how it’s affected people’s lifestyles?
    • What’s one skill you think everyone should learn, regardless of their career?
    • Share a wellness or self-care trend that you find interesting or beneficial.
    • How do you think your outlook on life has evolved over the past decade?
    • Describe a personal project or goal that you’re passionate about right now.
    • What’s your opinion on sustainability, and how do you think individuals can make a difference?
    • Tell me about an experience that shifted your perspective on work-life balance.
    • What’s the best piece of advice you’ve received about staying focused on long-term goals?
    • Share your thoughts on the importance of community involvement and volunteering.
    • What’s one activity or practice that helps you stay grounded in the present?
    • How do you manage social media use without getting overwhelmed?
    • What’s one skill or life lesson you think schools should teach more?

    Serious Things to Talk About

    • What are your love languages?
    • Share your core values and priorities.
    • What’s your attachment style?
    • Do you want to get married at some point in life?
    • Would you like to have kids?
    • Describe your expectations for a committed relationship.
    • What’s one nonnegotiable in a relationship for you?
    • Talk about your views on family involvement in a relationship.
    • How do you feel about balancing personal space and intimacy in a relationship?
    • What are your views on managing finances as a couple?
    • How do you prioritize work, personal time, and relationship time?
    • Share your take on religious beliefs and their importance in your life.
    • Do you want to stay living in one place or travel the world?
    • How do you handle stress, and what support do you need from a partner?
    • Talk about your expectations around loyalty and faithfulness in a relationship.
    • What’s your biggest fear when it comes to relationships, and how does it manifest?

    Deep Things to Talk to Your Boyfriend About Over Text

    • I’ve been thinking about how much you mean to me lately. It’s crazy how close we’ve gotten. How do you feel about it?
    • I really love that I can be myself with you. Do you feel like you can be your true self around me too?
    • You make it easier for me to trust again, even with things I’m still working through. Do you feel like you can trust me?
    • It’s kind of amazing how you just get me. Do you feel understood by me too?
    • Even when we’re not together, I still feel so connected to you. Why do you think that is?
    • I’ve never felt this comfortable opening up about my insecurities with anyone before. Do you feel safe being vulnerable around me too?
    • Sometimes I worry about being too much. Do you ever feel like that?
    • I don’t say this often, but I’ve grown so much because of what we have. It’s been really good for me. Do you feel like you’ve grown too ever since we’ve met?
    • I love that we can have real, deep conversations without it ever feeling forced. Do you think that too?
    • Being with you makes me want to be the best version of myself. Do you feel the same way?
    • I really appreciate how we can talk about things most people avoid. It makes me feel closer to you. Do you feel closer to me because of it too?
    • You’re the first person I’ve ever been able to be totally real with, even about the tough stuff. Do you feel like you can be totally real with me too?
    • I feel like I can tell you everything without feeling judged. Do you feel safe sharing things with me?
    • Some days I feel insecure, but then I remember I don’t need to be perfect for you to love me. Do you ever feel that way, or is it just me?
    • I love that we can talk about our future and it doesn’t feel overwhelming or scary. How do you feel when we talk about it?
    • It’s comforting knowing that even when I’m at my low, you’re still there, loving me. Do you feel supported by me when you are feeling down?

    Sharing something personal and following up with reflective questions deepens emotional connection by inviting open dialogue. It shows vulnerability, builds trust, and encourages the other person to share their own feelings. This creates a mutual exchange, fostering closeness and understanding while showing genuine interest in their perspective.

    What to Discuss With Your Boyfriend When You’re Bored

    • If we were in a zombie apocalypse, what’s the one item you’d insist on bringing and why?
    • If you had to wear a cartoon character costume every day for the rest of your life, which character would you choose?
    • Imagine you’re the ruler of a tiny island. What’s the first law you’d enforce?
    • If you could create your own infomercial for a completely useless invention, what would you be selling?
    • If you could swap your laugh with any animal sound, which one would you pick?
    • If our lives were made into a reality TV show, what would our dramatic storyline be about?
    • If we switched bodies for a day, what’s the first thing you’d do as me?
    • If we had to go undercover as spies, what would our secret identities be?
    • If you could have one completely bizarre item in your house that would freak out guests, what would it be and where would you place it?
    • If we had to communicate exclusively through emojis for a day, which would be our go-to three?
    • You’ve just been hired to write slogans for super mundane products like dishwashing soap. Which slogan are you rewriting first?
    • If you had to design a theme park based on something completely random, what would be the theme?
    • If you could challenge anyone in the world to a completely useless competition, who would it be, what would you compete in, and why would you win?
    • If we were stranded on a desert island but could choose one game to bring along, what would it be?
    • You just inherited a haunted house, but the ghost only does one incredibly silly thing — what’s their ghostly hobby?
    • If aliens landed right now and asked you to take them to our leader, who would you bring them to?

    These silly, entertaining prompts are perfect for when you’re bored. They can reignite the spark, prevent awkward lulls, and build a deeper connection over time. Keep the flow natural and fun — and maybe mix a few flirty remarks in there for good measure!

    How to Talk Intimately With Your Boyfriend Over Text

    Use texting mindfully

    While texting is a great way to stay connected, share affection, and coordinate plans, important conversations, and deeper emotions are best shared in person because tone and body language add layers of understanding that texts simply can’t convey.

    A chapter from the Handbook of Interpersonal Psychology explores how nonverbal cues — such as facial expressions, body language, gestures, eye contact, and tone of voice — play a crucial role in interpersonal interactions. 

    This study highlights how nonverbal cues help people interpret each other’s emotions more accurately, suggesting that face-to-face communication allows for richer, more nuanced exchanges than computer-facilitated communication.[1

    So, instead of describing an awkward, stressful situation at work via text, try messaging this: “I’m looking forward to chatting later about our day. You won’t believe what my boss said!”

    Compliment and express affection

    While texting shouldn’t replace in-person affection, it can be a lovely complement to it. 

    Sending thoughtful compliments or loving messages throughout the day can keep your emotional connection strong, especially when you’re apart. It’s like a modern-day love note — though I still love the charm of a handwritten note tucked into a pocket.

    For example, you could text, “I know you’re going to crush your presentation today!” or “Thanks for doing the dishes this morning, you’re the best.” 

    Simple, specific expressions of affection remind your partner that you notice the little things, making him feel appreciated and valued.

    Start with compliments that matter

    Compliments aren’t just surface-level pleasantries, they’re a powerful way to build emotional intimacy. 

    When you’re looking to engage in an emotionally intimate conversation, think beyond the usual “You look great” and try something more meaningful. A deeper compliment, like “I’ve been reflecting on how supportive you were during my stressful week. It meant the world to me,” touches on emotions and experiences that truly matter. 

    These thoughtful remarks show appreciation not just for their looks, but for their actions, making the person feel seen and valued. This type of compliment creates a space where vulnerability thrives, often leading to a deeper conversation. 

    It can help break through the usual chit-chat and foster genuine connection, leaving room for sharing more about what makes your bond special.

    Dare to be vulnerable

    In relationships, vulnerability is about sharing your feelings, even when it’s scary. Texting your boyfriend something like “I have never felt safe in a relationship before I met you” might seem like a small gesture, but it opens the door for deeper conversations. 

    Vulnerability fosters trust, and trust is the cornerstone of any healthy relationship. Expressing your feelings regularly can prevent emotional walls from building up, and can help bring down some of them too, ensuring that your relationship remains emotionally intimate.

    Ask reflective questions

    Asking reflective questions encourages deep thinking about personal experiences and emotions, sparking introspection. These questions are key for building self-awareness, emotional growth, and regulation. 

    Research published in Frontiers in Psychology highlights that reflection helps people understand their emotions, reducing negative responses and improving emotional intelligence, which strengthens empathy and trust in relationships.[2]

    So, instead of small talk, ask your boyfriend reflective questions like, “What’s something you’ve been thinking about lately?” or “What’s a goal you’re working on that I don’t know about?” 

    These questions allow you to explore his inner world, uncovering thoughts and feelings that might not come up in everyday conversations.

    Ask for his opinion and advice

    There’s a somewhat tiresome joke on the internet that women love to talk about emotions, while men are all about offering solutions — highlighting just how underdeveloped emotional communication still is globally. 

    But it’s not a made-up story. It makes sense. Men often feel more connected when they can offer advice or solutions, which is why they tend to jump into problem-solving mode when we just want them to listen.

    When texting your boyfriend, asking for his opinion on something like a tricky work situation or an emotional dilemma not only shows you trust him but also makes him feel valued. 

    So, sometimes, instead of simply venting, try texting, “I want to hear your take on this,” or “What would you do in my shoes?” It gives him a chance to feel involved and strengthens your bond. 

    Choose your timing wisely

    Timing is everything when it comes to discussing deeper, more sensitive topics. 

    Pay attention to when your boyfriend is more relaxed — perhaps in the evening or during a quiet weekend — and bring up emotional topics then. 

    Texting “I’d love to talk more about how we can handle stress better together” at an appropriate time can prevent unnecessary conflict and lead to more meaningful discussions. 

    The key is choosing moments when both of you can focus fully on the conversation.

    Opt for calls when emotions run deep

    When it comes to discussing emotional topics or building emotional intimacy, tone is crucial. Long text threads can easily lead to misinterpretation, but a phone call or in-person conversation allows for clearer communication. 

    If you’re feeling misunderstood or frustrated, instead of texting paragraphs, try this: “I feel like we’re not understanding each other. Can we talk on the phone?” It’s one of the best ways to strengthen your connection and avoid emotional miscommunication.

    Conclusion

    This ultimate list of things to talk about with your boyfriend is packed with deep questions and thoughtful, fun prompts to spark meaningful discussions. 

    Use these conversation starters to strengthen your bond, discover new sides of each other, and keep the connection alive with deeper and more meaningful discussions.

    Curious to learn more about being in a relationship? Check out the link.

    References

    1. Gifford, R. (2011). The role of nonverbal communication in interpersonal relations. In L. M. Horowitz & S. Strack (Eds.), Handbook of interpersonal psychology (pp. 171–190). Wiley.
    https://doi.org/10.1002/9781118001868.ch11

    2. Merkebu, J., Kitsantas, A., Durning, S. J., & Ma, T. (2023). What is metacognitive reflection? The moderating role of metacognition on emotional regulation and reflection. Frontiers in Education, 8.
    https://doi.org/10.3389/feduc.2023.1166195


    Author

    • Milena J. Wisniewska

      Milena might not be a relationship professor, but she's definitely been through it all, learned her lessons, and is here to spill the tea.She combines the wisdom of renowned relationship specialists with her own romantic adventures to offer relatable and practical advice.

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