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Deeper, Please! 45 Things to Talk About With Your Boyfriend

Is the conversation getting stale? Here’s a list of things to talk about with your boyfriend to reignite the spark between you two.
Editorial team
April 1, 2024
April 16, 2024
min. read
Table of Contents

A healthy relationship requires consistent, respectful communication. But that doesn’t necessarily mean you need to have a daily, super-serious “defining the relationship” talk. Sometimes, communication comes in the form of light-hearted, exciting conversation.

It doesn’t matter how long you’ve been together; you can always get to know your boyfriend better, building even more intimacy and trust. Plus, it’s a fantastic way to learn some of your partner’s weirdest and most embarrassing moments (and share your own). Spilling the tea is fun, even when it’s about yourself.

Many couples struggle with finding creative conversation topics, especially if they’ve been together for eons. But you’ll be surprised how much there is to learn once you delve into these unique questions to ask your boyfriend.

Getting to know him: 45 things to talk about with your boyfriend 

If quality time is your love language, you’ll want some intriguing conversation starters to keep the candles flickering and the wine flowing. Here are 45 conversation topics to help you and your boyfriend build emotional intimacy and comfort.

1. Are you a cat person or a dog person?

Let’s start with the most crucial question: dogs or cats? Ask why he prefers one over the other; he might have a fascinating bark-story.

2. What was your most awkward moment as a teenager?

Everyone has an embarrassing story from their years in middle and high school. Get to know him better by sharing your cringiest memories. Just remember to be kind, especially if he’s still sore about it.

3. When have you been the most proud of yourself?

Celebrate your BF’s wins by encouraging him to celebrate his own!

4. Who’s your celebrity crush?

Is he into twinky Timothee Chalamets or Taye Diggs daddies? Learning his celebrity crush might give you hints on how to coif your hair the next time you meet up.

5. What are your love languages?

Love languages like gift-giving, physical touch, and quality time are essential in relationships. Figure out which ones he prefers so you can become fluent.

6. Do you have any relationship deal breakers?

Ask him about deal breakers. Then, make a deal with yourself not to break them.

7. What’s your favorite movie?

If the relationship is fresh, ask about his favorite movie to gain insight into his personality. If you already know the answer, ask him why it’s his favorite.

8. Who was your first kiss? How was it?

A guy’s first kiss can be unforgettably romantic or eternally embarrassing. So, which one was his?

9. What are your guilty pleasures?

We should never feel ashamed to be ourselves. Still, everyone has that one thing they love but feel like they shouldn’t.

10. What’s your fondest childhood memory?

Stroll down memory lane with your boyfriend and learn about his childhood. Childhood memories often bring up intense emotions, so treat this conversation with care (and keep the tissues handy).

11. What’s at the top of your bucket list?

What experiences are on your boyfriend’s bucket list? Hopefully, you have some overlap!

12. What was your worst first date?

Who doesn’t have an embarrassing first date story? Get your partner to be specific about his strangest dating experiences and commiserate with him.

13. What was the craziest date you’ve ever been on?

Sometimes, the craziest date isn’t the first one. And crazy isn’t necessarily a bad thing!

14. Do you have a sexual fantasy you want to see fulfilled?

Pull out the pen and paper and ask your boyfriend about his sexual fantasies. And keep your phone handy in case you need to order a costume with priority shipping.

15. If you could trade places with a fictional character, who would it be?

Does your guy envy or emulate any fictional characters? Why would he want to live their life?

16. What are your thoughts on marriage?

The marriage question is a big one and maybe not a thing to talk about with your boyfriend over text, but it’s totally valid if you’ve been together for a while.

17. What’s a funny memory you have of you and me?

Reminisce on some of the best experiences in your relationship by asking him about his favorite memories.

18. What does your perfect day look like?

Is he seeking thrills or looking to relax at home? This is another question that requires active listening and maybe opening the notes app on your phone.

19. What relationship advice are you constantly giving your friends?

Maybe you can both use the advice to build a happy, healthy relationship.

20. What makes you laugh the most?

Humor is crucial in relationships, so learn how to make your boyfriend cackle!

21. When was the happiest you’ve ever been?

Ah, memories. This is another relationship question you can ask to watch your boyfriend’s eyes light up!

22. Have you ever been cheated on?

If he’s been cheated on, that experience probably informs how he approaches relationships to this day. The topic is an excellent thing to talk about with your boyfriend to get closer. This is another challenging subject you should handle with care.

23. Do you watch porn when I’m not around?

Porn can be part of a nutritious sex life. Plus, it tells you what he’s fantasizing about.

24. Where’s the craziest place you’ve had sex?

Get flirty and ask about his raunchiest casual encounters! This is a fun thing to talk about on the phone with your boyfriend if you want to get him in the mood from a distance.


25. What was your favorite TV show from childhood?

Learn more about his formative childhood years with this relationship question. His fondness for Blue’s Clues may explain why he goes wild whenever you wear a striped shirt.

26. What’s the most romantic thing anyone’s ever done for you?

Everyone can appreciate a romantic moment, even if you weren’t the one responsible.

27. What’s your favorite part about sex?

Learn what really gets your boyfriend’s sex drive in gear and use it to your advantage once that bottle of wine runs dry.

28. How do you feel about small talk?

If you’re reading this list, you probably got sick of discussing the weather. But maybe your boo loves small talk.

29. What’s the strangest food you’ve ever eaten?

What else is he willing to put in his mouth? This is a safe relationship question to break the ice.

30. What’s a hobby you wish you had taken up?

Does he regret quitting piano? Or maybe he always wanted to learn to salsa dance? Find out!

31. What does a healthy relationship look like to you?

Learn how he views a healthy relationship so you can cultivate one with him.

32. Do you have any regrets?

Asking about regrets can bring up some deep conversations. This topic might present an opportunity for you to help each other grow!

33. What’s the weirdest thing anyone has said to you during sex?

From the unexpectedly kinky (“Does puppy wanna yiff with me?”) to the totally uncalled for (“Damn, you’re really sweaty.”), we’ve all heard something shocking during a hookup.

34. What do you need most from a romantic or intimate relationship?

Even if he doesn’t know his love language, you can still find out if your partner needs something specific to feel safe and fulfilled.

35. What’s your happiest moment between us?

Build more emotional intimacy by chatting about the best of times.

36. Tell me about an awkward conversation with an ex.

Talking about ex-boyfriends isn’t always in the cards. But if it is, you have an opportunity to learn what not to say.

37. How can I make you feel more loved in our relationship?

Feedback is always welcome in a healthy relationship!

38. What beliefs do you consider a deal breaker?

Understanding his ideological boundaries sheds light on his moral compass.

39. What should be more normalized in society? Less?

Pet play? Male-pattern baldness? This intriguing relationship question can take you to many curious places.

40. Why didn’t things work out between you and your ex-boyfriend?

This is another potentially nerve-wracking topic, but it could yield some crucial information.

41. What’s something embarrassing you’ve said on a first date?

Maybe he isn’t great at flirting, or food flew out of his mouth while laughing. This is one of the funnier topics to talk about!

42. How can we improve our sex life?

Get more intimate and be open to making some changes.

43. Who was your childhood best friend? Do you keep in touch?

Take another peek back in time and learn about the relationships your partner had when he was itty bitty!

44. What’s the riskiest thing you’ve done?

Learning about his thirst for danger tells you whether your bucket lists are likely to align.

45. What is it about our relationship that drives you crazy? 

Crazy can be good! Let him interpret this question however he wishes.

Go all in with deep questions to ask your special someone

No subject should be off-limits with your boyfriend. Use these conversation starters to make your chats more flirty and fun. Just remember: Intimacy is developed over time. Be patient, stay open minded, and encourage honesty to build a better relationship!

Want to find a boyfriend or hookup who will talk all night about these topics? You’ll find him on Grindr! Download the Grindr app now and get started.

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