75 Questions to Ask Your Boyfriend That Will Make Him Open Up

It’s well known that men often communicate less in relationships. Psychology Today explains that this happens from fears of conflict, shame, and abandonment, influenced by social expectations that make it harder for men to show their feelings. In this context then, what are the best questions to ask your boyfriend to help him open up?

Staying curious about each other is one of the most effective relationship communication exercises, but certain topics can feel daunting or uncomfortable. Fortunately, there are question formats designed to make conversations easier, such as:

• Never have I ever…
• Who’s most likely to…?
• This or that…
• Would you rather…?

Even better, apps like the Couple Joy app have these questions built in, so you can dive in without worrying about what to ask next.

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In this article, we’ll share 15 examples for each type of question, which will hopefully make communication more enjoyable for both you and your partner.

😆 Silly Questions to Ask Your Boyfriend

Injecting humor into a relationship can ease tension, and one of the best fun things to do with a partner is playing a game of Never have I ever questions.

This format lets you explore your partner’s past without it feeling intrusive, turning potentially awkward revelations into playful moments.

Here are 15 Never have I ever questions to ask your boyfriend:

1. Never have I ever sent a text to the wrong person.
2. Never have I ever kissed a celebrity.
3. Never have I ever cried in public.
4. Never have I ever pretended to like a gift I didn’t.
5. Never have I ever pretended I was someone I'm not.
6. Never have I ever gone out without underwear.
7. Never have I ever used a pick-up line.
8. Never have I ever sung karaoke in front of strangers.
9. Never have I ever had a funny or embarrassing Zoom/online call moment.
10. Never have I ever spied on a conversation.
11. Never have I ever eaten something off the floor.
12. Never have I ever fallen asleep in a weird place.
13. Never have I ever tried a crazy food combination just for fun.
14. Never have I ever made up a story to sound more interesting.
15. Never have I ever tried to impress someone and completely failed.

✋ Good Questions to Ask Your Boyfriend to Know Your Relationship’s Dynamic

Understanding your relationship dynamics helps identify each partner’s tendencies and roles. “Who’s most likely to” questions provide a playful lens to see patterns in your relationship, such as who takes the lead in planning adventures or who tends to dream big.

Try these 15 questions to explore your relationship dynamic:

1. Who’s most likely to plan a spontaneous trip?
2. Who’s most likely to start a DIY project at home?
3. Who’s most likely to forget a birthday?
4. Who’s most likely to splurge on something unnecessary?
5. Who’s most likely to crack a joke at the wrong moment?
6. Who's most likely to cry during a movie?
7. Who's most likely to start a conversation with a stranger?
8. Who’s most likely to come up with a new conspiracy theory about the world?
9. Who’s most likely to go crazy for Christmas decorating?
10. Who's most likely to eat dessert for breakfast?
11. Who’s most likely to leave dishes in the sink for days?
12. Who’s most likely to get lost even with GPS?
13. Who’s most likely to sing in the shower?
14. Who’s most likely to take a nap anywhere, anytime?
15. Who’s most likely to overpack for a weekend trip?

💭 Hypothetical Questions to Ask Your Boyfriend

Hypothetical questions spark imagination and help you learn what matters most to your partner. They show how he thinks, what he values, and how he might react in different situations.

Would you rather questions can go from funny and impossible to serious and thoughtful, giving you a glimpse into your boyfriend’s personality and way of thinking.

Here are 15 hypothetical questions to ask your boyfriend:

1. Would you rather be able to go back in time or see the future?
2. Would you rather buy a house in the countryside or rent an apartment in a big city?
3. Would you rather win the lottery or forever be healthy?
4. Would you rather have a pause or rewind button for life?
5. Would you rather build a stable career or dedicate your life to traveling?
6. Would you rather be famous or unknown but rich?
7. Would you rather live without music or movies?
8. Would you rather explore space or the ocean?
9. Would you rather invest your money or treat yourself?
10. Would you rather lose all your money and valuables or lose all of the pictures you have ever taken?
11. Would you rather always have perfect weather or always have perfect sleep?
12. Would you rather have endless free time but no money, or endless money but no free time?
13. Would you rather master a new language instantly or a new skill?
14. Would you rather have a home with a massive library or a home with a massive kitchen?
15. Would you rather have a night out on the town or a cozy night in together every weekend?

🫦 Sexy Questions to Ask Your Boyfriend

Sexual topics can be delicate, but starting with playful options lowers pressure. In fact, a study in the Canadian Journal of Human Sexuality found that couples who joke about their sex lives are often happier in both sexual and overall relationship satisfaction.

One way to introduce humor and simplicity is through “This or That?” questions, where all your partner has to do is choose between two options (whether it’s a short description or a photo). No lengthy explanations required (unless you want to develop the conversation further), no pressure, and no awkwardness.

Some 15 sexy questions to ask your boyfriend:

1. Candlelit bedroom or steamy shower?
2. Lingerie or cozy pajamas?
3. Slow and sensual or fast and fiery?
4. Whispered compliments or playful teasing?
5. Massage first or kiss first?
6. Roleplay or spontaneous fun?
7. Bedroom playlist or silence?
8. Light bondage or free play?
9. Movie night cuddles or dancing in the living room?
10. New positions or favorite classic?
11. Sexy text messages or flirty voice notes?
12. Shower together or bathe together?
13. Slow kisses or passionate kisses?
14. Feather/light touch or deep massage?
15. Roleplay or foreplay?

🏡 Serious Questions to Ask Your Boyfriend

Once you’ve known each other for a while and feel ready to take the next step in your relationship, it’s important to start having deeper conversations. Talking about key topics before big changes happen can prevent misunderstandings later on.

The Couple Joy app includes an entire category called “Discuss before…”, filled with prompts to help you talk about sensitive subjects that often come up around major relationship milestones, such as:

• Moving in together
• Getting engaged
• Planning long-term finances
• Starting a family
• Buying a house
• Relocating for work

Here are 15 serious questions to ask your boyfriend when you want to move forward with your relationship:

1. What are your long-term career goals?
2. How do you feel about marriage and commitment?
3. How do you handle finances in a partnership?
4. What are your thoughts on children?
5. What values are non-negotiable for you?
6. How important is alone time versus together time?
7. How will we split the household chores?
8. Will we still go on regular dates after moving together?
9. Are you looking for a starter house or a forever home?
10. Are we able to cover all the costs needed for a child/children?
11. What role does religion or spirituality play in your life?
12. How do you feel about relocating for work or family?
13. How do you prioritize health and wellness for yourself and your partner?
14. How do you want to handle holidays and family traditions?
15. What’s your approach to planning for emergencies or unexpected events?

🥰 Conclusion

Choosing the right questions to ask your boyfriend allows you to explore emotions, desires, and shared goals in a thoughtful but fun way. Use the Couple Joy app to test all these questions (and explore 3,000+ more) and turn everyday chats into opportunities for growth and connection!