Great Questions Try Asking Your Boyfriend

Whether you’ve just started dating or been together for years, there are always many ways to bring the fun back into a relationship.

Sometimes all you need is a fun conversation to remind you why you fell in love in the first place. And what better way to start your conversation than with these fun and great questions for boyfriends?

We’ve listed a ton of great questions that you can use to start conversations. These can help make your guy feel special and keep your relationship exciting. Check them out and see which questions you want to ask him on your next date!

Photo by Josh Hild on Unsplash

Great Questions For Boyfriends

Fun Questions

Keep the mood light by asking your boyfriend some of these fun questions. They’re great for casually chatting with your man over coffee. They can even get him laughing as they share their answers.

  • Have you ever done anything crazy for me? 
  • What would you do if you got lucky and met your celebrity crush?
  • What’s the craziest lie you’ve ever told someone? 
  • What is your favorite date activity?
  • Is there a question you would never ask someone on a date?
  • What was the most embarrassing question someone asked you on a date, and how did you react?
  • What is the worst question someone has ever asked you on a date?
  • Have you gone on a date with someone who was uninteresting?
  • What’s one thing you would do if you could turn into a woman for the day?
  • What three items would you want to have if you were on a desert island?
  • Is there one toy or item that you’ve kept with you since childhood?
  • What was the worst online purchase you have ever made?

Deep Questions

Gain more insight and understanding about your man with these deep questions. These will surely reveal a side of him you might have never seen before. It will also help you explore your feelings and emotions more.

  • What qualities do you admire most about yourself?
  • What are the things that you’re most thankful for?
  • Who would like to live as for a day?
  • What are the things you have on your bucket list for this year?
  • What qualities do you like the most about your parents?
  • How do you deal with stressful situations?
  • Is there anything that you would like to alter about yourself?
  • How can you tell if someone is ready to get married?
  • Is there anything that you’re afraid to tell me?
  • What words hurt you the most?
  • What values or principles do you want your children to have?
  • What’s the worst heartbreak you’ve ever endured?
  • How would you define a healthy relationship?
  • Would you move to an entirely different country for love?

Alluring questions

Want to spice up the conversation on a date night? Try asking him these alluring and sexy questions. It’s sure to make your date a lot more romantic and memorable.

  • What kind of things do you do when there’s no one watching?
  • When was the last time you felt a great rush of adrenaline?
  • What do you think of when we’re kissing?
  • Which body part do you think is my greatest asset?
  • What is your biggest turn-off?
  • What is your biggest turn-on?
  • How would you define a “real man”?
  • What is your guilty pleasure?

Unique Questions

Be surprised at what you may learn from asking him these unique questions. These are sure to get him thinking and talking.

  • What would you tell your younger self?
  • Do you have an invaluable skill?
  • If you’re allowed to listen to only one song for your entire life, what would it be?
  • What quote do you live by?
  • What is your favorite book as a child, and why?
  • Have you ever fought with someone physically? What was the fight about?
  • What are the things you would do if you could travel back in time?
  • Are you a confrontational kind of person?
  • Are you the type of person to judge a book by its cover?
  • Would you take a bullet for someone? Who would it be?
  • If you only had one day left, what would you do?


Questions are a great way to start conversations and learn more about each other. They can help you understand your partner better and show that you care about their thoughts, opinions, and answers. Try out these questions for boyfriends on your next date and see where it goes!

Abir is a data analyst and researcher. Among her interests are artificial intelligence, machine learning, and natural language processing. As a humanitarian and educator, she actively supports women in tech and promotes diversity.

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